Justin Welsh Newsletter Strategy - 31 Emails Analyzed (2026)

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Mediocrity at scale.

hello@justinwelsh.me7/25/2026

Kit

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The machine is a mirror.

hello@justinwelsh.me7/18/2026

Kit

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Having fun is the new moat.

hello@justinwelsh.me7/11/2026

Kit

Stop sharpening your axe. You don't have a skill problem. You have this big problem instead. Read on my website ( https://b9bcc769.click.convertkit-mail4.com/gkupv4dmzqu5hl4p49durh8oxm3dofmh223kz/7qh7h2u92d6g68s9u6/aHR0cHM6Ly9qdXN0aW53ZWxzaC5tZS9lc3NheXMvYXhl ) · 4 min read Quick note: I’m kicking around an idea related to this issue that I mention at the end. Would love to hear what you think. There’s an old quote, credited to Abraham Lincoln, that if he had six hours to chop down a tree, he’d spend the first four sharpening his axe. I love that quote. I’ve repeated it probably a hundred times to colleagues over the course of my career. Because I believe that the people who win in their careers are the folks who prepare the longest, work on their skills, and show up doing the best possible version of their work. But for entrepreneurship, I think it’s the wrong advice. I know a guy I’ll call Ben. Ben ran sales at a healthcare tech company in San Francisco focused on pricing transparency. He went to an Ivy League school, and you could tell when you met him. He was super smart, sharply dressed, and well-spoken. But more importantly, he was a brilliant operator. The kind of guy who could build out complex go-to-market plans that left CEOs feeling confident. We came up in the same industry and knew most of the same people. But I was what you might consider a “poor man’s version” of Ben. He was running revenue at a company well north of $250 million, managing sophisticated partnerships and a complex sales process. I was at $70 million, without most of the complexity. We were both good at our jobs, but if you’d lined us up in 2018 and asked anyone to bet on who would be a successful entrepreneur, nobody would have picked me. Like we all assumed he would, Ben eventually went out on his own to build a healthcare technology consulting firm. And when things didn’t take off the way he expected, he followed the old Lincoln adage and sharpened his axe. He built more frameworks, better processes, and deeper methodologies that would resonate with clients. He believed that excellence alone would lead to success. But it turns out that working on getting better didn’t actually work. And the last time I spoke with him, his business still hadn’t found its footing. He was trying to make fractional work stick and applying for VP jobs back in the Bay Area. It’s hard to understand why Ben couldn’t translate his smarts, expertise, and excellence into successful entrepreneurship. Because by every measure of merit, he deserved to win. In 2019, I launched my own healthcare consulting business. I didn’t have the patience Ben had, and I didn’t have the runway to find out if being the best consultant I could be would eventually pay off. The pressure to make my business work fast was real. Going back to a regular job wasn’t something I wanted to do. So I took the opposite approach. Rather than trying to become the best consultant I could be, I decided that I was going to start putting myself out there in every way I could think of. I wrote on LinkedIn every single day. Posts about healthcare and sales and building teams, hiring, firing, go-to-market, and everything else I’d spent sixteen years learning. I hit the podcast circuit like an absolute madman. Hundreds of them. Any show that would have me. Any audience that might include a single person who needed what I had. Every morning, I scoured Google News and found all of the healthcare founders who had just announced a funding round, and sent them a DM. Congrats on the round. I’m a healthcare technology veteran from Zocdoc and PatientPop, and I love what you’re building. Let me know if I can be helpful. I sent thousands of those DMs over the course of two years. Some founders ignored me. Some responded. And some became the first clients in my new business. Then I did it all over again. DM. DM. DM. More posts. More comments. More podcasts. Networking event. Connecting two people. Cold email a VC firm. I was reaching out to anyone who I thought might need what I was offering or could point me in the direction of someone else who did. I didn’t even have a strategy. I was just swinging my axe. After a while, a few discovery calls started trickling in. Some of them came from writing valuable LinkedIn posts. A few from DMs that landed at just the right time. One or two from podcast appearances. Then, one of those appearances found its way to Jason Lemkin of SaaStr. Turns out he had also seen some of my posts on LinkedIn, and he invited me to speak on stage at SaaStr Annual in San Francisco. After my presentation, several founders lined up asking if I offered consulting. The recording of my talk hit YouTube, and even more calls started to come in. And then in April 2020, after posting on LinkedIn daily for seven months, one of my posts finally exploded. It generated millions of impressions, tens of thousands of engagements, and five thousand reshares. Thirty people booked calls that week. If you looked at any of those things in isolation, it’s easy to pass them off as luck. Jason Lemkin hearing me on some podcast. The YouTube video being seen by founders who just happened to need some help. A post going wild and hitting millions of impressions out of nowhere. I understand why each one looks lucky. But the truth is, you don’t get a one-in-a-thousand break without taking a thousand swings first. I’d been putting myself out there every single day, and eventually the math had to work out in my favor. The break that looks lucky from the outside is just compounded volume finally paying off. The craziest part is that I hadn’t actually gotten any better at consulting during my entire push for more exposure. My skills were basically the same. My expertise was hardly different than it had been the very first day I opened my business. What changed was that I had become almost impossible to miss. Ben had an exposure problem, not a preparation, excellence, or expertise problem. The market doesn’t reward the most talented people. It rewards talented people who are also visible. Once you’re past an above-average threshold of competence, “getting better” barely moves the needle. What moves the needle is getting your face and your brand and your thoughts and your expertise in front of as many relevant people as humanly possible. We don’t hear this growing up. We hear about working harder and getting better. That the best person wins out in the end, and the quality of your work will be what sets you apart. I just don’t think that’s true when you’re getting started as an entrepreneur. So if you’ve been trying to work your way out of a failing business by “improving your skills,” I grant you permission to stop. Because the number of people who know you exist is what matters right now. You’re talented just like Ben or me. Your axe doesn’t need any more sharpening. It needs you to start swinging. That’s all for this week. See you next Saturday. Cheers, Justin Welsh P.S. Exposure still seems to be the biggest issue for most entrepreneurs. I recently gave a 90-minute talk at a private mastermind to more than 50 six- and seven-figure creators on how I’m still growing on social in the age of A.I. (while most accounts are stagnating or declining). My process, systems, what’s working, what isn’t, etc. I’m considering turning it into a polished version that I can do live for readers, but it would depend on how many people are actually interested. It would be a paid ticket to cover the build, time, software for a large group, etc. But, as always, an affordable price. If you think it would be beneficial to you, you can learn more and let me know if you’re interested here ( https://b9bcc769.click.convertkit-mail4.com/gkupv4dmzqu5hl4p49durh8oxm3dofmh223kz/6qhx3rd6aoul8x5q56t9uk/aHR0cHM6Ly9qdXN0aW53ZWxzaC5tZS90aGUtdGFsa3Mvc29jaWFsLW1lZGlh ). 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Stop sharpening your axe.

hello@justinwelsh.me7/4/2026

Kit

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Manufactured certainty.

hello@justinwelsh.me6/27/2026

Kit

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Rich and broke.

hello@justinwelsh.me6/20/2026

Kit

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The two-speed problem.

hello@justinwelsh.me6/13/2026

Kit

Unreasonable. Read on my website ( https://b9bcc769.click.convertkit-mail4.com/8kuwprkx54foh26q607skhkoqo225a3hqq5wl/n2hohquvp034z0u0ug/aHR0cHM6Ly9qdXN0aW53ZWxzaC5tZS9lc3NheXMvdW5yZWFzb25hYmxl ) · 5 min read The best financial decision of my life was taking a job that paid $18,000 less than the one I already had. I was 28. My mom had emailed me the Craigslist ad. A door-to-door sales gig in New York City, for a company nobody had heard of, in a city I couldn’t begin to afford, and I was already drowning in credit card debt. Every reasonable person in my life told me to pass. I’m glad I didn’t listen to one of them. Over the last twenty years of my life, my seemingly unreasonable choices have been responsible for almost everything good that’s happened to me. This is something I think about a lot. How the choices that yielded the most positive results were never the ones that made sense on paper. And maybe you’re thinking that taking risks and “having courage” are, of course, the choices that lead to the good stuff. But I don’t think it’s really about that. I think it has to do with how choices compound over time and what happens when you make too many reasonable choices in a row. Think about it. The status quo looks a little something like this: Go to a good school and get good grades, take the reasonable job, say yes to the city the job wants you to move to, meet the guy or gal, date and get married, take the promotion, move again, have the kids, send them to good schools, take the next promotion, buy the house, and mow the yard. On it goes. And the fact is, every one of those choices is reasonable. Nobody could blame you for saying yes to the stuff that makes sense. But there’s a catch. Because every time you make a reasonable choice, it makes the next decision a little easier to make too, without thinking. It doesn’t matter if you’re facing a decision about the industry you’re in, the promotion you’re offered, or the titles you acquire along the way. Each next choice comes with a little less friction, every time. Another promotion? It’s more money. Sure. Move closer to the office? Will make life more efficient. Yeah, I don’t love the industry, but this offer from a competitor is pretty compelling. I should look at it. The aggregate total of all these reasonable choices creates a long chain. Each choice you make is one link, and each link makes the next choice a bit more automatic. Then somewhere around year 10 or 15 or 20, there’s so much momentum that breaking the chain feels downright irresponsible. Reckless even. So most people will never break the chain, and they just keep trucking along. What’s the worst thing that could happen? But one day you wake up 40 years later and realize you built your entire life this way, on autopilot, one reasonable choice at a time. And a lot of people who wake up there don’t like the life they find themselves in. The chain you linked together isn’t actually the problem, though. My old college roommate, Dave, has been at the same medical company in the same city he grew up in for the last 23 years. He’s married, has the kids, and from everything I hear, he’s happy as a clam. Last time I asked a buddy how Dave was doing, I heard, “He’s exactly the same as he was 20 years ago.” And that wasn’t an insult. Because the chain Dave built and the life Dave wants point in the same direction. I admire that. But for a lot of people, the chain is building in the opposite direction of the life they really want. But they can’t see it happening because each link they added was so small and so logical that they never stopped to question the direction the chain was going. This happened to me early in my career. When I graduated from college, I got into pharmaceutical sales because that’s what my Dad had done my whole life. I had a nice, American, middle-class childhood, and I figured that’s what I’d build for my family someday. But unlike my Dad, I wasn’t good at the job and got fired pretty fast. And with one pharma job on my resume, I felt like my choices started to narrow. So I applied for another pharma job and met the same demise a few years later. So I started applying again. Same industry, another terrible small town, same logic behind the choice. Three jobs, three nowhere towns, and three firings later, I was the biggest loser in my friend group. That Craigslist ad my mom sent me was for a startup called ZocDoc, and I had absolutely no business taking that job. I was already crushed by credit card debt, had a résumé full of firings, and I had a second offer sitting right in front of me that was, by far, a more reasonable choice. It was a sales job at a big medical device company back home in Cleveland that paid more than I was making. The reasonable choice was obvious. Take the Cleveland job, live near (or with) my family, pay down my debt, and turn my career around. If I’d polled all my friends and former colleagues at the time, nobody would have voted for New York. But I said yes to New York. I moved into my friend Mara’s apartment in Bushwick, Brooklyn. She had four other roommates, and I slept on a futon in the living room, next to a rolling rack that held my entire wardrobe. I woke up for my first day in a city I couldn’t afford. Within a few months of living in NYC, I was selling more ZocDoc subscriptions than anyone on the team, and I was good at something for the first time in my career. The company was growing fast, and we finally needed an office manager. Our CEO recruited a no-nonsense cocktail waitress he’d met in Chicago, talking her into moving to New York to work for a company she’d also never heard of. That waitress’s choice was just as unreasonable as mine. She’d just rented a new apartment in Chicago, painted the walls with her boyfriend of five years, and settled in for good. Then she left all of it to move to Brooklyn. Her name was Jennifer Kelly, and we’ve been married for 12 years. I replay that in my mind often. The Cleveland job was the reasonable and safe choice. But I can trace every good thing back to my unreasonable decision to take a chance on New York. In 2014, I made another unreasonable decision. Six months after getting promoted to work directly for the CEO, I decided to quit. ZocDoc had become one of New York’s first “unicorns,” and I walked away to take a VP of Sales job at a company with no funding and one salesperson. My friends (and especially my buddies at ZocDoc) thought I’d lost my mind. We were on a rocket ship, after all. Why leave a sure thing to manage one sales guy at a startup nobody believed in enough to even fund? But off I went, and I built a sales team to 150+ people doing $70 million in revenue. And eventually, a unicorn valuation of its own. Then I quit that too. Why? To build an online business by myself. I didn’t have a team, a title, or a salary. And it was the scariest and most unreasonable thing I ever did. I’m not sure I ever thought it would work. But I went on to build an eight-figure business over seven years, and that’s where I am today. Every one of those moves scared my friends and family at the time. But they all worked out better than the reasonable alternatives would have. If you’re reading this and you’ve heard stories like this before, I know how this comes off. “Guy takes risks, things work out, and now he tells others to be bold.” I know that luck is a much bigger part of my story than I’ll ever fully grasp. But I’ve only got a sample size of this one life. And I’m not claiming that breaking your chain will work out the same way mine did. But I do think it’s important to view the risks of unreasonable AND reasonable choices. People usually focus on the risks of the unreasonable choice and stop there. What if I fail? What if this choice doesn’t work out? What if everyone thinks I’m crazy for trying? Those are valid concerns. But nobody talks about the risks of sticking to the reasonable choices, compounded over decades. And I think those risks are bigger. It’s just slower and harder to feel the consequences. Because the unreasonable choices get loud, scary warnings, while the reasonable ones get decades of encouragement and approval. Every link is defensible, and everyone around you nods along and claps the whole way down. That’s why you can’t see it happening. Because nothing ever feels like the wrong choice. You follow the chain for decades, one reasonable link at a time, and you end up deep inside a life you never really chose. Nobody warns you about it because, from the outside, everything looks great. Thumbs up. When I realized this, I stopped asking questions the status quo wanted me to ask. Is this safe? Does the money make sense? Will people approve? Sure, those questions keep you employed, housed, and respectable. And there’s a time and a place for asking them. But they’re also the questions that build the chain over time. So instead, I started asking a different question: Does this life feel like mine? And once I started asking that, I couldn’t stop. Every few years, the chain started to get predictable and easy again. Reasonable choices began stacking up, the momentum building, and my autopilot would kick in. So, I’d make the conscious choice to break the chain. Quit my job, change the business, or move somewhere else. A slight pivot here, a new business model there, pack up and move to the mountains of Upstate New York. And each time, that worried voice in my head (and my friends and family) showed up to tell me I could be making a huge mistake, or…being unreasonable. But they’ve been wrong every time so far. The most unreasonable people I know aren’t always rich. Some run tiny businesses that venture capitalists would laugh at. Some of them just got sick of their corporate gigs and leaned into something more personal. And others just picked up their family and moved somewhere they felt most alive, and stopped feeling the need to explain their decisions. They’re not all successful by the common narrative. But their lives are their own. And I’d venture to guess that if you’re reading this, you know whether your life feels the way you want it to or not. When it doesn’t, most people call it something else. Being “tired”, “overwhelmed,” and “too busy”, “going through a rough patch”, or the kind of thing “everybody” deals with. You may have decided it’s ungrateful to even think that way. So you reach for the next link of the chain. The next promotion or the bigger house or the decision that makes total sense to everyone around you. And the chain gets one link longer and stronger. I’m not here to tell you to blow up your life. That would be foolish. I don’t know your life. And maybe your chain and life point in the same direction, like my old college roommate, Dave. If so, that’s something to celebrate. Because most people can’t say that. But if this essay touches a nerve, I’d encourage you not to explain it away. It’s not a weakness to question yourself. It’s just a small part of you that’s trying to figure out whether or not this life you’re living is actually yours. If it’s tracking in a direction you actually want to go. Most people will never stop to even consider it. Almost all of the risks you’ve been taught to fear are around unreasonable choices. Those risks are loud and obvious and pretty easy to talk yourself out of. The risks you’ll rarely think about are the invisible ones. It’s the reasonable choice you’re about to make, without even thinking, because it’s sitting right in front of you. That choice is easy, obvious, and pre-approved by everyone. And maybe, just maybe, very wrong. Cheers, Justin Welsh P.S. This is an essay I’ve been really excited to share. If you got this far, someone probably came to mind. Maybe a friend or family member whose chain is quietly pointing the wrong way, but who can’t see it because every choice looked fine on its own. Forward this to them. Don’t write a long note. Just say “thought this was worth 5 minutes, curious what you think.” Find me elsewhere X ( https://b9bcc769.click.convertkit-mail4.com/8kuwprkx54foh26q607skhkoqo225a3hqq5wl/48hvh7ume8r34ehqu7/aHR0cHM6Ly94LmNvbS90aGVqdXN0aW53ZWxzaA== ) · LinkedIn ( https://b9bcc769.click.convertkit-mail4.com/8kuwprkx54foh26q607skhkoqo225a3hqq5wl/wnh2h6uqp6wde2blux/aHR0cHM6Ly93d3cubGlua2VkaW4uY29tL2luL2p1c3RpbndlbHNoLw== ) · Instagram ( https://b9bcc769.click.convertkit-mail4.com/8kuwprkx54foh26q607skhkoqo225a3hqq5wl/reh8h9umrz0pggi6u6/aHR0cHM6Ly93d3cuaW5zdGFncmFtLmNvbS90aGVqdXN0aW53ZWxzaC8= ) · 1:1 call ( https://b9bcc769.click.convertkit-mail4.com/8kuwprkx54foh26q607skhkoqo225a3hqq5wl/08hwhgu25rd43lapu5/aHR0cHM6Ly93d3cuZXZlcnlleHBlcnQuY29tL2p1c3RpbndlbHNo ) You’re receiving this because you subscribed at justinwelsh.me ( https://b9bcc769.click.convertkit-mail4.com/8kuwprkx54foh26q607skhkoqo225a3hqq5wl/8ghqh3uovnl8m7hlu9/aHR0cHM6Ly9qdXN0aW53ZWxzaC5tZQ== ). 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Unreasonable.

hello@justinwelsh.me6/6/2026

Kit

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Your new rabbit hole.

hello@justinwelsh.me5/30/2026

Kit

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Small enough to see.

hello@justinwelsh.me5/23/2026

Kit

* * * ************************ There's no map for this. ************************ Read on my website ( https://b9bcc769.click.convertkit-mail4.com/0vu59q6oxgh9h95e5votlhv7vnp3etnhnndwz/3ohphdu3l683pzcp/d3d3Lmp1c3RpbndlbHNoLm1lL25ld3NsZXR0ZXIvdGhlcmVzLW5vLW1hcA== ) / Read time: 4 minutes The Saturday Solopreneur is brought to you by: Vibe Prospecting - Professional Prospecting in Claude ----------------------------------------------------- Connect Claude to 800M contacts, 150M companies. Find prospects, enrich leads, and build lists in chat. 30% off first package code: SOLO30 Try it for free ( https://b9bcc769.click.convertkit-mail4.com/0vu59q6oxgh9h95e5votlhv7vnp3etnhnndwz/48hvh7umez3mxwfq/aHR0cHM6Ly93d3cudmliZXByb3NwZWN0aW5nLmFpLz91dG1fc291cmNlPW5ld3NsZXR0ZXImdXRtX21lZGl1bT1uZXdzbGV0dGVyJnV0bV9jYW1wYWlnbj1zb2xvcHJlbmV1ZXImdXRtX2NvbnRlbnQ9c29sb3ByZW5ldWVy ) Back in 2009, I was a 28-year-old salesperson hawking healthcare software door-to-door in Manhattan. Many of the doctors I was calling on weren't much older than me. And after forming some friendships, I found myself joining a group of doctors for dinner one night. We ended up at a new Indian spot in Tribeca. Prem, our host and organizer for the evening, was a gastroenterologist. David was a well-known plastic surgeon. And Jessica was a young dermatologist, just starting to build her practice. They brought along a few of their younger friends who were still in med school. We all crammed into a table in the back, ordered way too much food, and after the second (or third) round of drinks, the conversation turned to careers. I remember feeling pretty good about mine at the time. I was new to the city, loving my job, and things were starting to click for the first time in my professional life. I was happy to be in New York, to be invited to a dinner with new friends, and not thinking much about where the conversation was headed. Then a young med student named Kristine started talking. She seemed to be about my age, if I were to guess. And she commanded everyone’s attention as she walked through her career plan with calm confidence. She’d finish her residency, followed by a fellowship, join a practice, work her way up, and eventually become a partner. The next two or three decades had been mapped out with such specificity, and I remember noting just how impressive she was. She could tell you, down to the year, exactly which step came next. I was working for a fast and furious startup at the time. Putting it kindly, we were building the plane as we flew it. Roles were being created and doled out weekly. People were getting relocated on a whim. Nobody knew what came next because "next" was being figured out in real time. As I sat listening to Kristine that night, I felt just how big the gap was between her world and mine. We were about the same age, just starting our careers, and working hard. But Kristine had a path that existed long before she arrived. And I was on a journey that would change every day, if not every hour. I thought back on that dinner several times over the years. It was just one of those nights that stuck with me for some reason. And it really popped back into my mind the further I got into building my own business. I finally understood what I'd felt sitting across from Kristine that night. ------ No map ------ Entrepreneurship isn't hard because the work is necessarily hard. It's hard because you're never quite sure what the work even is. You feel confused more often than you feel certain. You sit down to design a strategy and realize that there aren't just a few options to choose from. There are hundreds or thousands. Should you build this funnel or that one? Is it high ticket or low ticket that’s best for you? Audience first, or product first? Twitter or LinkedIn or YouTube or TikTok or Instagram, or all of them, or none of them, or some of them? And just when you think you've figured something out, the platforms change, the algorithms shift, a new trend arrives, and the entire landscape shuffles underneath your feet. Sound confusing? It is. Add to that thousands of people telling you they've cracked the code. Everyone has the cheat code, the framework, the playbook, and a done-for-you system. Some people are scamming. Some of them are telling the truth because it worked for them. The bad news is that their market isn't your market, their timing isn't your timing, and their personality isn't yours. You can follow their steps exactly and land somewhere insanely different. And that whirlwind feeling never really goes away. Even after years of building, finding something that works, and getting a little traction, there's always a new competitor, or a new tool, or a new threat that makes you feel totally lost. Like you’re starting from scratch again. I'm not sure I've ever felt like I've truly “made it.” I don’t actually think that feeling exists in this entrepreneurship game. I’ve always felt like, no matter how much success I had, that someone else had cracked the code faster or better than I had. And for a long time, I thought that was a personal failure of mine. Like everyone else had figured out the map, and I was the only one still wandering around asking, “Am I doing this right?” But, it turns out there’s no map for anyone in entrepreneurship. -------------------- Two kinds of careers -------------------- Most traditional career paths have a path you can follow that was sketched out long ago. It doesn’t matter if it’s medicine, law, most trades, or even becoming a professional athlete. The stages have been largely predetermined by what’s been proven to work. Do this first, this second, this third, end with this, and ta-da, you’ve made it. A doctor who worked her way to becoming a practice partner back in 1995 can jump on a call with a resident today and give them advice that still mostly applies, because the path is generally the same. Entrepreneurship has none of that. There are no predetermined stages. And even the things that look like stages aren’t. Getting into Y Combinator isn't a step in the way that getting into medical school is a step. Hitting 100,000 followers means everything to one person’s business and nothing to someone else’s. The next marker of success doesn't exist until you invent it. And you're out there trying to figure out what the next stage looks like while simultaneously trying to win at whatever the heck stage you're currently stuck in. And, unfortunately, most good career advice is stage advice. Do this specific thing at stage three of your career, and you’ll move to stage four. But the entrepreneur isn't at stage three of anything. They're at some random, unmarked point on a path they're making up in real time. That's why so much entrepreneurship advice fails to land. The advice giver tells us what they did, as if the “doing” is the part that transfers. But it’s not. What transfers (if anything) is the judgment they built by living through it. The hard-won instincts. The experience and wisdom they gained in their market, at their moment. But most of the time, you can't even borrow stuff like that. You just have to build your own. And when the advice and the frameworks and the playbooks don't work? Most people will blame themselves. They weren't focused enough, or didn't execute correctly, or gave up too soon. But working without a map isn't a personal failure. For an entrepreneur, that's just the job. And it’s one of the hardest jobs in the world. --------------- The bottom line --------------- When I think back to that dinner in Tribeca, I think about Kristine. I imagine she's somewhere around step 14 of 20 on her way to practice partner. Of course, there's absolutely nothing easy about that journey. But sometimes I envy the predictability of it. Mostly, though, I love the challenge of entrepreneurship. I love the fact that I can stop, pivot, and do something completely different tomorrow or next year. I love that when people ask what I do for a living, I'm never quite sure what to say. I love that when I have a new idea, I can go take some action on it and find out if it’s brilliant or moronic. There's a freedom in that which most linear career paths will never offer. What I didn't know at that dinner table in 2009 is that Kristine and I weren’t on the same path and never would be. We just happened to be about the same age, sitting in the same room, eating the same Indian food. Her map already existed. And mine never would. So here's my question for you this week: What path are you still following that was built for someone else's situation? Reply and tell me about it. I can't respond to everyone, but Jennifer and I read every response, and we love hearing from you. That's all for this week. See you next Saturday. Justin Welsh Find me on X ( https://b9bcc769.click.convertkit-mail4.com/0vu59q6oxgh9h95e5votlhv7vnp3etnhnndwz/wnh2h6uqp9dq0nsl/aHR0cHM6Ly90d2l0dGVyLmNvbS90aGVqdXN0aW53ZWxzaC8= ), LinkedIn ( https://b9bcc769.click.convertkit-mail4.com/0vu59q6oxgh9h95e5votlhv7vnp3etnhnndwz/reh8h9umr9pm6dc6/aHR0cHM6Ly93d3cubGlua2VkaW4uY29tL2luL2p1c3RpbndlbHNoLw== ), Instagram, ( https://b9bcc769.click.convertkit-mail4.com/0vu59q6oxgh9h95e5votlhv7vnp3etnhnndwz/08hwhgu25042lrfp/aHR0cHM6Ly93d3cuaW5zdGFncmFtLmNvbS90aGVqdXN0aW53ZWxzaC8= ) or Book a 1:1 Call ( https://b9bcc769.click.convertkit-mail4.com/0vu59q6oxgh9h95e5votlhv7vnp3etnhnndwz/vqh3hmuo726ow9sw/aHR0cHM6Ly9pbnRyby5jby9KdXN0aW5XZWxzaA== ) Market your brand or business to 175,000 readers ------------------------------------------------ Sponsor The Saturday Solopreneur ( https://b9bcc769.click.convertkit-mail4.com/0vu59q6oxgh9h95e5votlhv7vnp3etnhnndwz/m2h7h6u3pkx344cl/aHR0cHM6Ly93d3cuanVzdGlud2Vsc2gubWUvc3BvbnNvcnNoaXA= ) and put your brand or business in front of 175,000+ solopreneurs, entrepreneurs, authors, creators, and makers. 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There's no map for this.

hello@justinwelsh.me5/16/2026

Kit

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Freedom. Sort of.

hello@justinwelsh.me5/9/2026

Kit

* * * ********************** Sweat the small stuff. ********************** Read on my website ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpepxkztxh69mpdx5s5hnnlkr/3ohphdu3g035enip/d3d3Lmp1c3RpbndlbHNoLm1lL25ld3NsZXR0ZXIvc3dlYXQ= ) / Read time: 3 minutes The Saturday Solopreneur is brought to you by: Lettuce Solo Summit: Free day of masterclasses ---------------------------------------------- We surveyed 600+ solopreneurs. The ones who grow are more intentional. One free day, eleven sessions to help you get there. May 14, it's free. Save your free spot ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpepxkztxh69mpdx5s5hnnlkr/n2hohquv0mv9zos0/aHR0cHM6Ly9sZXR0dWNlLmNvL3NvbG8tc3VtbWl0LTIwMjYtcmVnaXN0cmF0aW9uP3V0bV9zb3VyY2U9cGFydG5lciZ1dG1fbWVkaXVtPWVtYWlsJnV0bV9jYW1wYWlnbj1KdXN0aW5fV2Vsc2hfTWF5XzI2X1NTX25ld3NsZXR0ZXI= ) Hire Your AI CEO for $25/Month ------------------------------ Denovo builds your website, business plan, brand assets, videos, and pitch decks — then finds your customers and investors. All from an idea. Hire Your AI CEO ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpepxkztxh69mpdx5s5hnnlkr/n2hohquv0mv9zos0/aHR0cHM6Ly93d3cuZGVub3ZvLmRldi8= ) When I publish this newsletter, replies come in fast and furious. And Jennifer and I love to read them. We get everything from, "I feel like you're in my head," to "This wasn't one of my favorites." Responses come in all shapes, sizes, and tones. And there’s always a handful that are not nice at all. Someone calling me a fraud, or yelling at me because I didn’t use my personal brand to support a political injustice near and dear to them, or someone just letting me know how much they hate my writing. All of that is to be expected when you write to 180,000+ people every week. And when I get a reply where someone made a special effort to be extra mean, I've got seven years of practice letting it roll off my shoulders. But it doesn't always. Last week, a curt response slipped past my defense shield and got under my skin pretty badly. Not because it was a particularly clever barb. Because it questioned my authenticity and honesty, without offering any reasoning behind the attack. And forty-five minutes later, there I was stewing about it when Jennifer yelled up that lunch was ready. I'd drafted five different replies, none of them right. And when I looked up at the clock, I realized this nonsense had stolen a good chunk of my most productive hours. "What the f!@# am I doing?” I literally yelled that out loud to myself. Then I shut my computer and went down to lunch. For the rest of the day, that really gnawed at me. Not the email itself. The forty-five minutes of wasted time on something that didn't deserve it. The fact that I'd given part of the best hour of my morning to one guy with a chip on his shoulder, drafting a reply that wasn't going to change his mind anyway. I thought I was past getting irritated and letting things like this control part of my day. But it turns out, I'm not. And after thinking about this for a while, I'm not sure anyone gets past this kind of thing. Nobody’s too successful for this -------------------------------- A few years ago, I clapped back at Alex Hormozi’s wife online. She’d posted something I disagreed with, and I threw a jab that racked up thousands of engagements from people agreeing with me. If you’ve followed me online for any period of time, you know that going after people’s opinions isn’t really my thing. Looking back, I wish I hadn’t done that. And, of course, an hour later, Alex replied angrily. The exact same way that I’d react if someone were taking shots at Jennifer online. A few minutes later, I refreshed, and his comment was gone. He'd deleted it. And then he shot me a DM, and we talked it through. I said I was wrong for writing it, and he said he shouldn't have written his reply, and that was that. Alex is worth nine figures, has millions of followers, and built his career around discipline and not caring what other people think. If he’s not past letting random negativity get under his skin, then who is? I know I’m not, and I'll bet you aren't either. The lie nobody wants to admit is a lie -------------------------------------- A big part of the self-help industry is built on the premise that we shouldn’t let this kind of stuff bring us down. That we should train ourselves to be impervious to what other people think about us. Richard Carlson's "Don't Sweat the Small Stuff" was a massive bestseller that promoted the idea. To be clear, the book itself is a lot more careful than its reputation. But the dumbed-down version that so many people parrot sounds a lot like this: Do enough work, build the right habits, get successful enough, and the petty stuff stops mattering. You stop taking things personally. You’ll become the calm, unbothered sage on the other side of it all. I think this is total BS. I’ve worked with (and been friends with) some incredibly successful people for the last 20 years of my life. And I’ve watched nearly all of them fire off responses they regret, send nasty 3 a.m. emails, and get derailed by insults that shouldn’t matter. And I’ve done it myself. The idea of the “unbothered guru” is marketing. It’s not a real human state that most people will ever reach. And the people who tell you they don't care are usually either lying, numb, or selling you something. Most often it's the third. Because "I figured out how to stop caring about what other people think" is a much better book pitch than "I still get bothered, I just recover faster now." Let’s be realistic ------------------ If you’ve practiced the art of letting insults roll off your shoulders, but you still get bothered from time to time, you’re not broken or defective. You're just a human being with a pulse, doing work that you care about, around people whose opinions sometimes land a lot harder than you'd like. That’s who I am, too. The part of me that was drafting a bunch of replies to that mean email is the same part of me that cares enough to rewrite a sentence eight or nine times to get it right. When my stomach drops because someone takes a shot at me online? That’s the same part of me that cares enough to show up every week and do this work in the first place. Those feelings and that passion exist on the same wire. Cut one, and you cut both. The skill you want to build here isn’t total apathy. It’s noticing the derailment faster. It’s recovering more quickly. It’s being able to breathe and meditate through the times when you’re feeling most irritated. I've gotten better at all of that. Stuff that used to ruin my day now barely makes it 30 minutes. But this make-believe version of you who never gets bothered? I just don’t think that person exists. And if they do exist, you might not even like them very much. They'd be a less passionate worker and spouse, a less interested friend, and probably someone the people closest to you wouldn't even recognize. How and why we care about the things we do is our essence. So the next time someone tells you to rise above it, stop sweating the small stuff, or to let it all go, you have my permission to politely ignore them. There's no shame in caring. It’s simply up to us to recognize it faster and reduce the amount of time it knocks us off our game. So here's my question for you this week: What’s something that really heats you up, that you know, deep down, is a waste of your time? Reply and tell us about it. We can't reply to everyone, but Jennifer and I love hearing from you, and we read every response. Even the mean ones. That's all for this week. See you next Saturday. Justin Welsh Find me on X ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpepxkztxh69mpdx5s5hnnlkr/48hvh7um8vmd40iq/aHR0cHM6Ly90d2l0dGVyLmNvbS90aGVqdXN0aW53ZWxzaC8= ), LinkedIn ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpepxkztxh69mpdx5s5hnnlkr/wnh2h6uq6nq2ewul/aHR0cHM6Ly93d3cubGlua2VkaW4uY29tL2luL2p1c3RpbndlbHNoLw== ), Instagram, ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpepxkztxh69mpdx5s5hnnlkr/reh8h9umz4mlgmt6/aHR0cHM6Ly93d3cuaW5zdGFncmFtLmNvbS90aGVqdXN0aW53ZWxzaC8= ) or Book a 1:1 Call ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpepxkztxh69mpdx5s5hnnlkr/08hwhgu2rv263gcp/aHR0cHM6Ly9pbnRyby5jby9KdXN0aW5XZWxzaA== ) Join 10K+ entrepreneurs in my business Masterclass: --------------------------------------------------- The Creator MBA Masterclass ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpepxkztxh69mpdx5s5hnnlkr/8ghqh3uonzo6m9bl/aHR0cHM6Ly9sZWFybi5qdXN0aW53ZWxzaC5tZS9jcmVhdG9yLW1iYS1tYXN0ZXJjbGFzcy8_Y291cG9uX2NvZGU9Q01CQTIwMjZGTEFTSFNBTEU= ) is my complete business playbook. Every framework and system I used to grow my following to 1.5M and my business to $12M in revenue at 90% margins. Learn how to finally monetize your expertise! Your Email Preferences: Your email address is b@email.gomodulr.com Change your account details ( https://preferences.convertkit-mail4.com/4zu9eg03ozsehpepxkztxh69mpdx5s5hnnlkr )↗ ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpepxkztxh69mpdx5s5hnnlkr/vqh3hmuorlo9z8hw/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) Unsubscribe from all emails ( https://b9bcc769.unsubscribe.convertkit-mail4.com/4zu9eg03ozsehpepxkztxh69mpdx5s5hnnlkr )↗ ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpepxkztxh69mpdx5s5hnnlkr/vqh3hmuorlo9z8hw/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) 30 Main Street PO Box 448, Accord, NY 12404-9998

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Sweat the small stuff.

hello@justinwelsh.me5/2/2026

Kit

* * * ****************** Selective editing. ****************** Read on my website ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h65nmxgczhw4lwl28anh00gpq/vqh3hmuoroxprpcw/d3d3Lmp1c3RpbndlbHNoLm1lL25ld3NsZXR0ZXIvZWRpdGluZw== ) / Read time: 5 minutes The Saturday Solopreneur is brought to you by: Grow Faster With A Plan That Actually Works ------------------------------------------- Any AI can invent a “plan.” LivePlan validates ideas, forecasts revenue, and builds a plan that actually makes money. Used by 1M+ founders. Try LivePlan Free ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h65nmxgczhw4lwl28anh00gpq/l2heh6ul7l037lsg/aHR0cHM6Ly93d3cubGl2ZXBsYW4uY29tL3BwYy9haS1wbGFuLWJ1aWxkZXItZnJlZT91dG1fc291cmNlPXNhdHVyZGF5c29sb3ByZW5ldXImdXRtX21lZGl1bT1lbWFpbCZ1dG1fY2FtcGFpZ249bmV3c2xldHRlcnM= ) Jennifer and I just wrapped up a winter sabbatical in Northern California and returned home to Upstate New York last week. Unfortunately, my sleeping has been wacky since we got back, and I've been waking up at about 4 a.m. each morning. I can't just lie there awake, so I head downstairs to catch up on email from our living room couch in the dark. So there I was this past Monday morning when an email came through from a reader. She was responding to a recent newsletter ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h65nmxgczhw4lwl28anh00gpq/wnh2h6uq6q5w6vil/aHR0cHM6Ly93d3cuanVzdGlud2Vsc2gubWUvbmV3c2xldHRlci9tYWNoaW5lLW9yLWxpZmU= ) where I mentioned shutting down my two courses that generated 75% of my revenue. Her note was short and kind, and she wrapped it up saying: "I wish I were the kind of person who could make bold moves like that so easily." I looked at that line for a minute, because I wasn’t sure that "bold" was the right word for what happened. I'd just gotten tired of being the guy who sold LinkedIn courses, and the decision certainly didn't feel brave from my perspective. And I don't think of myself as a bold person. When I think of bold moves, I think of people like my friend Steve Schlafman ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h65nmxgczhw4lwl28anh00gpq/reh8h9umzm20zeb6/aHR0cHM6Ly93d3cuc3RldmVzY2hsYWZtYW4uY29tLw== ) and the moves I've watched him make over the course of his ever-changing career. And no move was bolder than walking away from his venture capital fund. Back in 2021, Steve was a week from launching his own fund, and fifty investors had already committed. He'd raised millions of dollars and put in a year of hard work leading up to the big launch. But there he was, about to send an email to all those investors, basically saying, "I've changed my mind, and this is not happening after all." Yikes. One morning, he finally sent that email. Back then, I didn't know Steve. He was just one of my favorite writers on Twitter because I liked how his brain worked and the thoughtfulness he wrote with. And I remember when he tweeted a link to this essay about shutting down his fund ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h65nmxgczhw4lwl28anh00gpq/08hwhgu2r2odr7fp/aHR0cHM6Ly93d3cud2hlcmV0aGVyb2FkYmVuZHMuY28vcC93YWxrZWRhd2F5 ), and how I felt reading it for the first time. Weirdly, I was jealous. Not because he was taking back control of his career. I simply envied his boldness. He was someone who could stare down a giant, scary decision, understand the cost, and pull the trigger anyway. I've spent most of my life avoiding confrontation of any kind, and writing an email like Steve's (let alone sending it) would have probably made me physically ill. I remember closing his essay and thinking, "I'm just not built like that." About a year later, Jennifer and I moved to a small town up in the Hudson Valley of New York, for reasons that had nothing to do with Steve. But it turned out Steve lived a few miles up the road from our new house. He saw on Twitter that I'd moved up here, and he reached out to initiate a coffee date. I was half star-struck and half weirded out that one of my favorite writers on Twitter suddenly knew I existed. Rereading it ------------ As I was lying there thinking about that reader calling me bold, I remembered Steve's essay and pulled it up again. And after four years of actually knowing the author, it read a bit differently. Just a few paragraphs down the page, four words in particular stood out: "I was scared shitless." Steve had written about sitting at his kitchen table that morning, trying to work up the courage to hit send. His heart rate spiking. Butterflies going wild in his stomach. Weeks of agonizing before that morning. Long talks with his coach, his therapist, and his wife. In his own words, he was scared shitless. It was all right there on the same pages I'd read back in 2021. Clear as can be, in plain English. Steve had been terrified to make the big move that I could only remember as bold. The interesting part is that back then, I hadn't registered any of it. I don't know what to call that. Because I didn't just miss it. Missing something sounds like an accident. It was more like selective editing. My brain read Steve's essay and trimmed it down to the version that I needed it to be. It kept the part where he sent the email, and cut the whole part where he felt like throwing up first. I guess I'd needed that edited version because the real one calls into question who I am. My ability to handle discomfort. If I thought Steve had been as scared as I would have been and did it anyway, what the hell does that say about me? So I took all of his honesty and whittled it down until it let me off the hook. I'm just not built like that. I texted Steve -------------- On Tuesday afternoon, I texted Steve to ask if I could write about him this week. He said, of course, and added something I wasn't expecting. Yes, he'd been nervous and scared. But he'd also been running small experiments for years. Coaching a few clients on the side, testing whether the work felt right, and seeing if he could actually walk away from the VC world and land in a good spot. By the time he sat down at his kitchen table to send that email, he wasn't risking his entire career. He already had evidence he'd be okay. He sent me an article by Jim Collins called "Fire Bullets, Then Cannonballs. ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h65nmxgczhw4lwl28anh00gpq/8ghqh3uono0lngtl/aHR0cHM6Ly93d3cuamltY29sbGlucy5jb20vY29uY2VwdHMvZmlyZS1idWxsZXRzLXRoZW4tY2Fubm9uYmFsbHMuaHRtbA== )" The idea is that before you fire the big cannonball, you fire small bullets first to see if you can hit the target. Then, once you've got the aim down, you fire with conviction. "From the outside, it looked bold," Steve wrote. "But I knew I was going to nail the landing." I thought about that for a minute, because it made my 2021 selective editing job even worse. Not only did I edit out Steve’s fear, but I also deleted the years of preparation that made the fear survivable for him. I'd been envying this one dramatic, bold moment, while completely erasing everything that made the moment possible for him. Steve and I at dinner this past Thursday. The first friend hang we after arriving back from California. It turns out that bold movers aren't just scared people who do the thing anyway. They're scared people who've also been preparing for a long time, and then make the big move. Athletes and astronauts. Prepared and scared shitless at the exact same time. As I flipped back to the email from my reader, I realized she was seeing this one bold moment without any of the work that led up to it. What my reader was really saying -------------------------------- She called the course shutdown bold, but I'd been pivoting away from tactical social media and solopreneur guides for over a year. Writing newsletters in a style that feels more authentic to where I am now. Paying attention to which ones landed and which ones felt hollow. Overhauling other parts of my business behind the scenes. By the time I actually shut those courses down, it wasn't some blind leap of faith. It was the last step of a long, slow process that she couldn't see from her vantage point. I think she's doing what I did to Steve. Seeing the single moment. Selectively editing the work underneath it. Using that version as evidence that some people are just "built to move that way." Just not her. I've been guilty of this for most of my life. I've created stories about people who seem to be built differently from me, and used those stories as permission to stay stuck and comfortable. Steve was one of those stories before I ever knew him personally. I'm not saying fear is irrelevant. Sometimes it's telling you something important, and you should listen to it. But there's a real difference between listening to your fear and waiting for it to go away before you decide to do anything. Nobody I know has ever done a hard thing after the fear completely subsided. They did it while the fear was still loud, usually with some serious preparation alongside it. The bottom line --------------- It turns out that the Steve I envied in 2021 never existed. He was a character I needed to believe in so I could stay comfortable in my own life. The real Steve worries and second-guesses and gets scared. He also runs experiments before he makes a bold move. He moved while he was scared, wrote honestly about it, and I edited out the fear and the preparation because a different story was more useful to me. I haven't written back to my reader yet. I'm not exactly sure what to say. Maybe just that the move she called bold didn't feel bold from where I was. That most of what looks like boldness is probably just someone who's been preparing for a while, got tired enough of one thing to start another, and then made the move scared shitless. So here's my question for you this week: Whose story have you edited down so you can keep telling yourself, “I’m just not built like that?” Reply and tell me about it. While I can't reply to everyone, Jennifer and I read every response, and we love hearing from you. That's all for this week. See you next Saturday. Justin Welsh Find me on X ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h65nmxgczhw4lwl28anh00gpq/dphehmuene40n5fl/aHR0cHM6Ly90d2l0dGVyLmNvbS90aGVqdXN0aW53ZWxzaC8= ), LinkedIn ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h65nmxgczhw4lwl28anh00gpq/e0hph0u7o7p0o5s7/aHR0cHM6Ly93d3cubGlua2VkaW4uY29tL2luL2p1c3RpbndlbHNoLw== ), Instagram, ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h65nmxgczhw4lwl28anh00gpq/7qh7h2u959ko5du9/aHR0cHM6Ly93d3cuaW5zdGFncmFtLmNvbS90aGVqdXN0aW53ZWxzaC8= ) or Book a 1:1 Call ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h65nmxgczhw4lwl28anh00gpq/z2hgh7uexe43x6az/aHR0cHM6Ly9pbnRyby5jby9KdXN0aW5XZWxzaA== ) Join 10K+ entrepreneurs in my business Masterclass: --------------------------------------------------- The Creator MBA Masterclass ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h65nmxgczhw4lwl28anh00gpq/x0hph3ue0erw06hg/aHR0cHM6Ly9sZWFybi5qdXN0aW53ZWxzaC5tZS9jcmVhdG9yLW1iYS1tYXN0ZXJjbGFzcy8_Y291cG9uX2NvZGU9Q01CQTIwMjZGTEFTSFNBTEU= ) is my complete business playbook. Every framework and system I used to grow my following to 1.5M and my business to $12M in revenue at 90% margins. Learn how to finally monetize your expertise! Your Email Preferences: Your email address is b@email.gomodulr.com Change your account details ( https://preferences.convertkit-mail4.com/75u4zlq5x6s8h65nmxgczhw4lwl28anh00gpq )↗ ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h65nmxgczhw4lwl28anh00gpq/6qhehoulelk7e8s9/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) Unsubscribe from all emails ( https://b9bcc769.unsubscribe.convertkit-mail4.com/75u4zlq5x6s8h65nmxgczhw4lwl28anh00gpq )↗ ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h65nmxgczhw4lwl28anh00gpq/6qhehoulelk7e8s9/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) 30 Main Street PO Box 448, Accord, NY 12404-9998

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hello@justinwelsh.me4/25/2026

Kit

* * * ****************** Synthetic purpose. ****************** Read on my website ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh6dp4x5fvhqel5xodboh446nw/48hvh7um89vqllbq/d3d3Lmp1c3RpbndlbHNoLm1lL25ld3NsZXR0ZXIvc3ludGhldGljLXB1cnBvc2U= ) / Read time: 5 minutes The Saturday Solopreneur is brought to you by: An unfiltered look at performing at the highest level in sports, business, and life. ----------------------------------------------------------------- In Earned, my friend Chris Pronger shares the real story behind his journey from a raw young player to the Hockey Hall of Fame and Stanley Cup champion. It’s not just a memoir. It’s a playbook for building standards, owning your decisions, and showing up when it matters most. One of my favorite recent reads. Grab your copy today! ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh6dp4x5fvhqel5xodboh446nw/wnh2h6uq64nv76hl/aHR0cHM6Ly93d3cuYW1hem9uLmNvbS9FYXJuZWQtR3JlYXRuZXNzLUhvY2tleXMtRmllcmNlc3QtQ29tcGV0aXRvcnMvZHAvMTYzNzYzNTAyOC9yZWY9c3JfMV8xP2NyaWQ9N1JCNFlNS0hDWVYyJmRpYj1leUoySWpvaU1TSjkuS09LY0gyb0ZTREg2alFRTkp6WEFZMUc5STVkNmF6M000R0VtSXhHSC0yZy5oemYtUDRIaDMzNWFYWTlnNFQtSG0tQ2M1cG03M1R6YVNYaFE4d2FPSjRZJmRpYl90YWc9c2U= ) I'm usually up by 5:30 am with a big cup of coffee and my laptop open, wild-eyed and ready to get after it before the sun's even up. And just about every day, I end up doing the same thing with my quiet morning. I open Claude and run the same financial numbers I've run hundreds of times before. I tinker with how our stock portfolio should grow, different budgeting scenarios, and withdrawal strategies. I've toggled every variable hundreds of times, and I already know what the results say. But I run the numbers again anyway, like maybe this time, some new answer will appear. When it doesn't, I move on to the next thing. I think a lot about our cost of living, because our spending is directly tied to how much money I need to make, and how long I have to keep making it. I dream about cheaper living. So the next thing I do is research where money goes the furthest in the world, where the weather's great year-round, and there's good food and wine and walkability and enough people who speak English. I already know these answers, too. I can recite them from memory by now. But maybe today I'll discover that fairytale place that's never popped up before. Then I sketch out what an ideal day or week should look like after I make whatever change I'm considering next in my life and business. How I'll fill up my purpose bucket, my exercise bucket, and my friend bucket. I want every piece of my life accounted for and predictable, laid out in front of me like a blueprint. I've been like this since I was a kid. But every morning, after all the ceremony, I'm in the same place. The path hasn't gotten clearer, and the choices are still unmade. No amount of spreadsheeting and research has made the uncertainties more certain. So I go on with my day and wake up the next morning to do it all over again. I've been stuck here a long time. ---- Dale ---- Last week, Jennifer and I took our friend Dale ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh6dp4x5fvhqel5xodboh446nw/n2hohquv0gm5qma0/aHR0cHM6Ly93d3cubGlua2VkaW4uY29tL2luL2RhbGVnaWJib25zLw== ) out to dinner here in San Francisco. Dale's 61, married to the love of his life, lives on a 100-acre farm in Southern Indiana, and helps consultants launch and grow their businesses. He's been a member of our community for the past year, and he'd traveled all the way to California to attend one of our events. Dale's one of those rare people who listens more than he talks. He asks thought-provoking questions instead of giving answers. And when he finally says something, there's genuine care and curiosity in his words. Like I said, rare nowadays. So when we sat down with Dale for dinner, I didn't give him a polished version of how things are going for me. I told him about the morning routine I've found myself stuck in. The spreadsheets, the research, and the planning loops that never go anywhere. I told him I'd been trying to figure out the next chapter of my life for more than a year, and how I want to know exactly what it'll look like before I push the ball forward. Dale sat back with his Cabernet and asked me questions for a while. He was patient while I talked myself in circles for a bit. And Jennifer finally jumped in. She told Dale that ambiguity throws me off. Like, genuinely upsets me. That she hates watching me struggle to enjoy the present because I'm always trying to be three steps ahead. Dale nodded along, finished a few bites of his burger, and then asked me a question I didn't have a great answer for. "I'm curious. Do you know what you're actually looking for when you open Claude and do all of that planning work and spreadsheets? Because it sounds like you already know what the numbers say." I answered something about needing more assurance. But even as I was saying it, I could hear myself copping out. The spreadsheet gives me the same answers every single time. Sensing I was flailing a bit, Dale didn't push it. He just nodded again, smiled, and said: "That question is worth thinking about, ya know…" and then we changed the subject. But his question stuck. ------------- The treadmill ------------- I woke up the next morning with a jolt. Dale's question was still rattling around in my head. I went to the gym and got on the treadmill, and the question gnawed at me. What am I looking for when I open that spreadsheet? It can't be "assurance" or "confidence" because the same answer sits in the same damn cell on Google Sheets every morning. So what am I even doing? Then, two miles into my five-mile walk, it dawned on me. I'm not looking for an answer. I'm looking for a problem to solve. I've been a problem-solver my whole adult life. For the last 17 years, I've woken up every morning with some target to hit, some number to chase, or a system to build or fix. Startup revenue goals. Sales teams. A business to grow from zero. Every morning had a clear purpose because there was always something that needed figuring out. And I'm a good figure-outer. That's been my thing for as long as I can remember. Then I figured a lot of it out. I built a successful business. I made money. I chose the quieter life. All choices made on purpose, and all the right calls. I genuinely believe that. But now I'm sitting in the life that I've chosen, and there's no quota. There's no dashboard that turns green when I've won the day. There's no urgent problem that needs me. And for a guy who spent almost two decades feeling most like himself when he was solving a big problem, this quiet space is hard to sit in. I keep finding myself wondering what my purpose looks like now. The Claude exercise isn't about getting the information I need. It's giving me the feeling of working on something important. A "synthetic purpose," I guess. A manufactured problem I get to solve for an hour every morning, so I can feel like the old version of myself that I know and understand. And when the hour's over, and the answer hasn't changed, I wait for tomorrow so I can do it again. ----------- The pattern ----------- I started thinking about just how many people I know who do some version of this. I have a great friend from high school who found himself deep in debt with the trifecta: credit cards, student loans, and car payments. Over several years, he got laser-focused on climbing his way out. He got an app with a countdown timer, put together a weekly plan with his wife, and the two of them got to work. When he finally made his last debt payment, he told me it was one of the best days of his life. But a few months later, he felt lost without the tracking, the weekly number crunching, and the shared goal. So he and his wife signed up for a real estate investing class and started obsessing over rental property metrics and taking on debt to acquire some properties. To me, that seemed crazy for someone who just climbed his way out, but he needed something with a number attached to it that he could chase, too. I think about the 180,000+ people who read this newsletter every week. Successful solopreneurs, founders, consultants, and creators. People who wake up every day, ready to build and solve and optimize. And I can't help but wonder how many of you have already solved the problem you originally set out to solve, and are now quietly manufacturing new ones just to keep the old identity going. I've spoken to and received emails from thousands of you by now. Folks who hit their revenue milestone and immediately raised it, not because they needed more money, but because the goal itself is what gives their mornings purpose. An old friend emailed me recently about how she keeps launching new offers every quarter, even though her core business is booming. In her last email, she admitted that she does it because "sitting still makes her feel lazy." But she might be the least lazy person I know! And I can't tell you how many founders I know who could step back tomorrow, but don't and won't. Because stepping back means sitting with silence, and silence means facing questions they don't really want to answer. I've been all of those people at certain points in my life. And I've realized that money and success don't eliminate our need for purpose. It just takes away the easy version of it. The targets, the goals, and the stuff with all of the numbers attached. And when the easy version of purpose disappears, trust me…your brain will invent problems to solve before it lets you sit without one. --------------- The bottom line --------------- The morning after the treadmill, I woke up at 5:30 again. Made my coffee. Sat down at the kitchen island with my laptop. I went over to Claude out of habit, but this time I stopped myself. My brain begged me to open it and start running the spreadsheet. To crunch the numbers one more time, to find the "secret city," and to plan one more version of my week, budget, and future. It would have felt like I was doing something important. But I wasn't, and I haven't been for months. I've been manufacturing the feeling of making progress on a question I've already answered. Because the alternative is admitting I don't have a big problem to solve right now. And when I don't have a big problem to solve, I'm not sure who I am. So rather than fall back into the old habit that morning, I opened a blank Notion page and wrote this newsletter to you instead. I still don't know what comes after you stop manufacturing purpose and start sitting with the fact that some of your biggest problems might be behind you. I'm probably going to be figuring that out for a while. But I know that the "spreadsheet life" isn't it. I also know that a 61-year-old guy from Indiana asked me one question over a burger, and it cracked something open that a year of 5:30 mornings couldn't touch. So here's a question that might do the same for you: Have you ever struggled with a “synthetic purpose” yourself? Keeping yourself busy with something because you’re unsure of what your actual purpose is? If you’re comfortable sharing, reply and tell me. While I can't respond to everyone, Jennifer and I read every response, and we love hearing from you. That's all for this week. See you next Saturday. Justin Welsh Find me on X ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh6dp4x5fvhqel5xodboh446nw/reh8h9umz74vdru6/aHR0cHM6Ly90d2l0dGVyLmNvbS90aGVqdXN0aW53ZWxzaC8= ), LinkedIn ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh6dp4x5fvhqel5xodboh446nw/08hwhgu2rxvwe6cp/aHR0cHM6Ly93d3cubGlua2VkaW4uY29tL2luL2p1c3RpbndlbHNoLw== ), Instagram, ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh6dp4x5fvhqel5xodboh446nw/8ghqh3uon3zpdmul/aHR0cHM6Ly93d3cuaW5zdGFncmFtLmNvbS90aGVqdXN0aW53ZWxzaC8= ) or Book a 1:1 Call ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh6dp4x5fvhqel5xodboh446nw/vqh3hmuor4l30wiw/aHR0cHM6Ly9pbnRyby5jby9KdXN0aW5XZWxzaA== ) Join 10K+ entrepreneurs in my business Masterclass: --------------------------------------------------- The Creator MBA Masterclass ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh6dp4x5fvhqel5xodboh446nw/l2heh6ul74ev2dfg/aHR0cHM6Ly9sZWFybi5qdXN0aW53ZWxzaC5tZS9jcmVhdG9yLW1iYS1tYXN0ZXJjbGFzcy8_Y291cG9uX2NvZGU9Q01CQTIwMjZGTEFTSFNBTEU= ) is my complete business playbook. Every framework and system I used to grow my following to 1.5M and my business to $12M in revenue at 90% margins. Learn how to finally monetize your expertise! Your Email Preferences: Your email address is b@email.gomodulr.com Change your account details ( https://preferences.convertkit-mail4.com/o8unwm0plofqh6dp4x5fvhqel5xodboh446nw )↗ ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh6dp4x5fvhqel5xodboh446nw/m2h7h6u3z9v05xtl/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) Unsubscribe from all emails ( https://b9bcc769.unsubscribe.convertkit-mail4.com/o8unwm0plofqh6dp4x5fvhqel5xodboh446nw )↗ ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh6dp4x5fvhqel5xodboh446nw/m2h7h6u3z9v05xtl/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) 30 Main Street PO Box 448, Accord, NY 12404-9998

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Synthetic purpose.

hello@justinwelsh.me4/18/2026

Kit

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The machine or the life.

hello@justinwelsh.me4/11/2026

Kit

* * * ************* Pick a table. ************* Read on my website ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h656qr3hzhwrg0g2kinh00gpq/25h2h9u39wmrgos8/d3d3Lmp1c3RpbndlbHNoLm1lL25ld3NsZXR0ZXIvcGljay1hLXRhYmxl ) / Read time: 4 minutes The Saturday Solopreneur is brought to you by: Learn AI workflows and replace 80% of them ------------------------------------------ Join Outskill's 2-day LIVE AI Mastermind where you'll build automations and create personalized agents. Start Learning Now ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h656qr3hzhwrg0g2kinh00gpq/qvh8h8udwpkgv8hg/aHR0cHM6Ly9saW5rLm91dHNraWxsLmNvbS9KVVNUSU5XRUxTSEFQUjI= ) When I landed at a startup job in NYC in 2009, I spent the first six months in what many people called "the worst territory." Staten Island. I'd commute an hour and a half from Bushwick, which meant two different trains, followed by a ferry over to the island just to get my day started. I had no car, which is still wild to think of. Sometimes I'd have to walk 30 or 45 minutes to get from one cold call to the next. By the end of my first winter, I'd worn giant holes in the bottoms of my dress shoes, and every time I stepped in a puddle or walked through snow, my socks were soaked for the rest of the day. One day, after I'd finally arrive back at the office in SoHo to log my sales calls, I noticed something interesting going on in the sales pit. Two groups of people. Two very distinct tables. One group of reps clustered together to complain about how impossible the job was. The quota was unrealistic. Territories weren't fair. Not enough inbound leads. "This place doesn't want us all to succeed," I once overheard. The others nodded in agreement, like it was some brave thing to say. And then there was the other group of reps. The folks who didn't have time for those types of conversations because they were too busy figuring stuff out. They’d huddle up to compare notes on what was working, borrowing each other's talk tracks, and staying late to prep for the next day. If someone left before 9 p.m., somebody would always yell, "Half day?" across the floor. Nobody in this group talked about whether the conditions were fair. They were determined to succeed. Early in that job, I sat down at the second table. I wanted to be around the people who were killing it, and I loved the energy. I didn't know at the time that I was making one of the most important decisions of my career. -------- Michelle -------- Michelle joined our company on the customer success team a few months after I started. She'd taken a pay cut and a step backward in her career to be there. On paper, it didn't make much sense. She'd come from a job paying more money and a title with a lot more prestige. I’d earned the opportunity to train new employees (while still having to perform at my sales job), and I remember her first day because of something she said during onboarding. We were going through the usual orientation stuff, and I was sharing the slide decks, when she looked at me and said, "I'm going to move through the ranks here." Not "I hope to move through..." or "I'd love to move through..." She said it like you'd tell someone your name. Matter of fact, in case I was interested. I'd already trained a lot of new hires by that point, and most of them spent training nodding along and trying not to look overwhelmed. But Michelle was different. She had this energy where you just knew she was going to be a problem, and I mean that in the best possible way. And a few weeks later, I watched her prove it. A doctor called in, furious about something that wasn't really our fault. Most people on the CS team would try to get through a call like that as fast as possible. Defuse, apologize, move on. Or, better yet, hand it off to a manager. But Michelle stayed on that call for half an hour, at least. She listened to the rant without rushing the customer off the phone. She worked through the issue slowly and methodically. And by the end of the call, she'd turned that doctor around 180 degrees. When she hung up, she slammed the phone down, pointed right at me, and yelled, "That's gonna be a renewal!" Then she walked over to a teammate who'd been struggling with a similar situation and walked him through exactly what she'd done. Michelle and I still say that to each other when we hang out and something goes well. "That's gonna be a renewal!" We remember it fondly. That was Michelle. Every problem was something to figure out. She eventually brought that mindset and attitude from CS over to the sales team, and from sales into management. And after a few more years, she left and kept going onto bigger roles at other companies with more responsibility and more impact. Today, Michelle is the CEO of a well-known creative agency doing over $25 million in annual revenue. And I can still hear her on that first day telling me she was going to move through the ranks. She wasn't predicting her future. She had already decided it. ---- Josh ---- Josh joined our company around the same time Michelle did. He came from a big pharma company with a recognizable name and a bigger paycheck. And he was resentful about the pay and the job requirements from the moment he walked in the door. I can remember one day when we were sitting in bean bag chairs, eating seaweed crisps (or whatever "startup snack" was lying around), and Josh was venting about his territory. I asked how his calls had gone that day, and he complained about having to make cold calls in the first place. He thought a junior salesperson should be making cold calls on his behalf so he could spend his time on deals. But there we were, sitting in bean bag chairs at an early-stage startup. I tried to share what was working for me, but Josh wasn’t interested. "That's easy for you to say. You've already gotten traction." It irked me to hear this while I was wearing shoes with big holes in them. Naturally, Josh found the second table fast. He joined the group that spent time complaining about injustices instead of figuring out how to make some sales. And that group confirmed his beliefs every day. The quotas were unfair, leadership didn't care, and the system was designed for them to fail. They had each other's backs in failure, and it probably felt like solidarity. But nothing about those conversations ever made any of those people better at their jobs. And one day, Josh just didn't show up for work. Last time I looked, he'd been an Account Executive at a bunch of tech companies for six months here, eight months there, and so on. ------------------ What I think about ------------------ The thing that jumps out at me about Michelle and Josh isn't that their outcomes were so wildly different. It's that their outcomes were determined before either of them made a single call. They worked on the same floor, with the same product, quotas, leadership, and pay cut story. They'd made similar sacrifices to walk through the same door. But Michelle viewed her sacrifice as an investment, and Josh viewed his sacrifice as a loss. They both made that decision early. And from that point forward, every day in their jobs became proof of the stories they’d already chosen. When I look at the people from Josh's table on LinkedIn today, so many years later, most of them are still bouncing around. A few years here, a few years there. I don't see a lot of upward momentum. I imagine they're still playing the same characters, just at different companies now. --------------- The bottom line --------------- I've been building my own business for almost seven years now. The tables look different. No sales pit or bean bag chairs. But the choice is still there. And candidly, some days I feel like sitting down at the complainer’s table. An article I spent a lot of time writing bombs with readers. My email open rates drop for a few months. The algorithm changes, and my reach tanks. It would probably feel good to find someone who agrees that it’s all so unfair. That the platform screwed me, or the market has shifted. That it's harder than it used to be. And maybe some of that is even true. But I’ve seen what happens when you sit at that table and tell yourself that story. Michelle chose her story on day one. I remember it because she told me. And I sat down at the same table because I saw a group of people whose future felt bright. I wanted to be around the folks who were jamming out, and I’m so glad I did. So here's my question for you today: Which table are you sitting at? Will you find a way to succeed, despite conditions you can't control? Or will you wait for a "fair" that may never arrive? Reply and tell me what you think. I can't respond to everyone, but Jennifer and I read every email, and we love hearing from you. That's all for this week. See you next Saturday. Justin Welsh Find me on X ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h656qr3hzhwrg0g2kinh00gpq/g3hnhwum9wq7n3s3/aHR0cHM6Ly90d2l0dGVyLmNvbS90aGVqdXN0aW53ZWxzaC8= ), LinkedIn ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h656qr3hzhwrg0g2kinh00gpq/9qhzhdudwr5kxdiz/aHR0cHM6Ly93d3cubGlua2VkaW4uY29tL2luL2p1c3RpbndlbHNoLw== ), Instagram, ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h656qr3hzhwrg0g2kinh00gpq/3ohphdu3mgp6r4up/aHR0cHM6Ly93d3cuaW5zdGFncmFtLmNvbS90aGVqdXN0aW53ZWxzaC8= ) or Book a 1:1 Call ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h656qr3hzhwrg0g2kinh00gpq/n2hohquvq07wgrs0/aHR0cHM6Ly9pbnRyby5jby9KdXN0aW5XZWxzaA== ) Join 10K+ entrepreneurs in my business Masterclass: --------------------------------------------------- The Creator MBA Masterclass ( https://b9bcc769.click.convertkit-mail4.com/75u4zlq5x6s8h656qr3hzhwrg0g2kinh00gpq/48hvh7uml8xz9kuq/aHR0cHM6Ly9sZWFybi5qdXN0aW53ZWxzaC5tZS9jcmVhdG9yLW1iYS1tYXN0ZXJjbGFzcy8_Y291cG9uX2NvZGU9Q01CQTIwMjZGTEFTSFNBTEU= ) is my complete business playbook. 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Pick a table.

hello@justinwelsh.me4/4/2026

Kit

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Just tell me when you’ll be here.

hello@justinwelsh.me3/28/2026

Kit

* * * ************* Thief of joy. ************* Read on my website ( https://b9bcc769.click.convertkit-mail4.com/wvuwk5zdl6fghk7nl4zh7hnzpzm59b8hwwn80/z2hgh7ue6drq45tz/d3d3Lmp1c3RpbndlbHNoLm1lL25ld3NsZXR0ZXIvdGhpZWYtb2Ytam95 ) / Read time: 4 minutes The Saturday Solopreneur is brought to you by: Free Workshop: Build a $10k/Month Newsletter in 2026 ---------------------------------------------------- Join Tuesday's private workshop for TSS readers. Start a newsletter, scale to 1,000 readers, and launch ads, digital products, or services. Save Your Free Seat ( https://b9bcc769.click.convertkit-mail4.com/wvuwk5zdl6fghk7nl4zh7hnzpzm59b8hwwn80/p8hehqu4675n3msr/aHR0cHM6Ly9jbGFzcy50aGVmZWVkbWVkaWEuY29tL3NhdHVyZGF5LXNvbG9wcmVuZXVyLXdvcmtzaG9wP3V0bV9jYW1wYWlnbj1TYXR1cmRheVNvbG9wcmVuZXVyJnV0bV9zb3VyY2U9cGFydG5lcg== ) Get up to $100k in free AWS credits! ------------------------------------ Spendbase handles the entire application process. Startups Claim your credits! ( https://b9bcc769.click.convertkit-mail4.com/wvuwk5zdl6fghk7nl4zh7hnzpzm59b8hwwn80/p8hehqu4675n3msr/aHR0cHM6Ly9odWJzLmxpL1EwNDczLU1HMA== ) When I was 27, my friend Cassie bluntly asked me how much money I was making. We were sitting at Bar Louie in Columbus, Ohio, after I'd driven two hours from Toledo to visit her for the weekend. We were ten minutes into our dinner conversation when she came right out with the question. "How much are you making now at your job?" Up until that moment, I hadn't really thought about whether my salary was good enough. And I certainly didn't think it was a problem. I was making $45K plus some measly commissions, and that wasn't keeping me up at night. None of my friends in Toledo were making much more than that. Most of my colleagues were in the same range, give or take $10K, and that was based on their experience. I was a 27-year-old kid from a small farm town in Ohio, and it had never occurred to me that I should be earning some massive salary, like $100,000, by age 27. In my head, people who made $100K+ lived in penthouses in NYC, and that just wasn't my world. So when I told Cassie my salary, I wasn't expecting a competition of any sort. I was just answering a question. But she let out a big laugh. She hadn't intended to be mean. It was more like a laugh of disbelief. I can still remember her voice and response: "Oh, my God! I can't believe you're not making six figures yet! I'm making $110K. I always thought you'd make it way before me." And Cassie had every reason to think that. We'd interned together in college, selling Yellow Pages ads door-to-door for a company called University Directories. I won the sales pitching contest at our training program, and everyone expected me to be successful at sales when we got out in the real world. But I was immature, had zero discipline, and I was completely lazy. The talent was there, but everything around it was missing. After college, our careers went in completely different directions. Cassie got a sales job at a big box flooring company and steadily worked her way into bigger roles over the next six years. Meanwhile, I got into pharmaceutical sales and spent that same time getting fired from jobs in tiny Midwest towns I didn't even want to live in. Three towns in seven years, bouncing from one to the next, underperforming, and repeating the cycle of failure. But I wasn't sitting in that booth at Bar Louie feeling sorry for myself before Cassie told me her salary. I was fine, just catching up with a college friend over dinner. And then a few sentences about her salary blindsided me. Suddenly, I was losing at something I hadn't even known was a competition. -------------- The drive home -------------- I drove back to Toledo a few days later, and I remember the drive more than the rest of that dinner. Snaking through Route 23 with nothing but my thoughts and a big coffee. I turned the radio off and drove along in silence, replaying Cassie's laugh in my head. And I started doing the math I'd never done before. She was making more than twice as much as I was, and she wasn't even bragging. She was genuinely confused about why I hadn't figured it out yet. Ten minutes before Cassie asked the question, I was doing fine. I was content. And 30 seconds after I heard her salary, I fixated on how far behind I was. How many years would it take to close the gap? Had I been deluding myself about my potential this whole time? It stung. That feeling of being behind rarely comes from an honest assessment of your own life. It comes from moments like my dinner at Bar Louie. From learning about someone else's number or title or milestone. Ten minutes before you knew it, you were okay. And ten minutes after, you're an utter failure. But the only thing that really changed was you learning information about someone else. -------------------------- What the scoreboard missed -------------------------- If you'd asked me on that drive back home what my career would look like in 10 years, I wouldn't have had much good to say. Probably something vague about hoping to find a sales job I could keep for more than a year. Within two years of that night in Columbus, I'd stumbled into a job at a startup in New York City and started winning real sales contests. Within four years, I'd run sales teams across multiple cities. And within eight years, I was a Chief Revenue Officer at a $500M company in Los Angeles. A decade after that night in Columbus, I began building what would become an eight-figure, one-person business. None of that was visible from the driver's seat of my Ford Escape on Route 23 back in 2008. I couldn't even get a whiff of this career. And if Cassie had asked me that night where I'd be at 37, I probably would have said something depressing (and inaccurate). You feel behind because you only know how to read the current scoreboard, and scoreboards are just snapshots of a specific moment. They can tell you exactly where things stand right now, but they're terrible at predicting what happens next. ----------------- Cassie's timeline ----------------- This isn't a story about me winning and Cassie losing. We both ended up winning. She's still working at the same flooring company and living in Ohio 18 years later. And she's thriving. She found her thing early on and has been building on it for almost two decades. That's a career almost anyone would be thrilled to have. Cassie wasn't ahead of me at Bar Louie. She was just earlier on her timeline. And I wasn't behind. I was just a bit later on mine. Two completely different trajectories, pacing on different schedules. The comparison that felt so devastating at 27 turned out to be meaningless. I was comparing two people on completely different paths using the same measuring stick, and that ruler couldn't capture what would eventually happen for either of us. I didn't start building my online business until my late thirties. Almost any snapshot of my career along the way could have looked behind compared to someone else. In retrospect, the timing was exactly what it needed to be. I just couldn't see it while I was living it. I'm not sure anyone can. --------------- The bottom line --------------- The worst thing about feeling behind is that it makes you rush. I know because that's how I responded. After that conversation, I jumped at an open Territory Associate job in St. Clair Shores, Michigan, with a big medical device company. It actually paid $5K less than what I'd been making before, but I took the role because I heard reps got their own territories after a year and "made the big bucks." The rep I was supporting made $600K, and I'd never heard of such a thing in my life. So I chased it. I took the pay cut to chase someone else's number. And when I finally got my own territory in Allentown, PA, I ended up getting fired again. So there I was, back where I started, in another small town I didn't like, and feeling even further behind than before. Careers, businesses, and even relationships don't follow straight lines. They can flatline, or dip, or stall for what feels like forever before they compound into something massive that nobody saw coming. If I could go back and talk to my 27-year-old self, driving back to Toledo on Route 23, I wouldn't tell him to work harder or find a better strategy. I'd tell him the scoreboard is going to start looking wildly different in a few years. That he doesn't need to compare himself to anyone other than previous versions of himself. And that he has no idea what's coming. But I'm not sure 27-year-old me would have listened to any of that. So here's my question for you this week: Where in your life are you rushing because you feel behind? And what would change if you stopped comparing your timeline to someone else's? Reply and tell me about it. While I can't reply to everyone, Jennifer and I read every response, and we love to hear from you. That's all for this week. See you next Saturday. Justin Welsh Find me on X ( https://b9bcc769.click.convertkit-mail4.com/wvuwk5zdl6fghk7nl4zh7hnzpzm59b8hwwn80/x0hph3ue27d5r2sg/aHR0cHM6Ly90d2l0dGVyLmNvbS90aGVqdXN0aW53ZWxzaC8= ), LinkedIn ( https://b9bcc769.click.convertkit-mail4.com/wvuwk5zdl6fghk7nl4zh7hnzpzm59b8hwwn80/kkhmh2unw92kdqhk/aHR0cHM6Ly93d3cubGlua2VkaW4uY29tL2luL2p1c3RpbndlbHNoLw== ), Instagram, ( https://b9bcc769.click.convertkit-mail4.com/wvuwk5zdl6fghk7nl4zh7hnzpzm59b8hwwn80/7qh7h2u9l4prk2s9/aHR0cHM6Ly93d3cuaW5zdGFncmFtLmNvbS90aGVqdXN0aW53ZWxzaC8= ) or Book a 1:1 Call ( https://b9bcc769.click.convertkit-mail4.com/wvuwk5zdl6fghk7nl4zh7hnzpzm59b8hwwn80/owhkhwuw98l2k2iq/aHR0cHM6Ly9pbnRyby5jby9KdXN0aW5XZWxzaA== ) Join 10K+ entrepreneurs in my business Masterclass: --------------------------------------------------- The Creator MBA Masterclass ( https://b9bcc769.click.convertkit-mail4.com/wvuwk5zdl6fghk7nl4zh7hnzpzm59b8hwwn80/z2hgh7ue6drq4liz/aHR0cHM6Ly9sZWFybi5qdXN0aW53ZWxzaC5tZS9jcmVhdG9yLW1iYS1tYXN0ZXJjbGFzcy8_Y291cG9uX2NvZGU9Q01CQTIwMjZGTEFTSFNBTEU= ) is my complete business playbook. Every framework and system I used to grow my following to 1.5M and my business to $12M in revenue at 90% margins. Learn how to finally monetize your expertise! Your Email Preferences: Your email address is b@email.gomodulr.com Change your account details ( https://preferences.convertkit-mail4.com/wvuwk5zdl6fghk7nl4zh7hnzpzm59b8hwwn80 )↗ ( https://b9bcc769.click.convertkit-mail4.com/wvuwk5zdl6fghk7nl4zh7hnzpzm59b8hwwn80/p8hehqu4675n3ptr/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) Unsubscribe from all emails ( https://b9bcc769.unsubscribe.convertkit-mail4.com/wvuwk5zdl6fghk7nl4zh7hnzpzm59b8hwwn80 )↗ ( https://b9bcc769.click.convertkit-mail4.com/wvuwk5zdl6fghk7nl4zh7hnzpzm59b8hwwn80/p8hehqu4675n3ptr/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) 30 Main Street PO Box 448, Accord, NY 12404-9998

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Thief of joy.

hello@justinwelsh.me3/21/2026

Kit

* * * ********************************** Missing someone who doesn’t exist. ********************************** Read on my website ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh69wlq2tquqwoxk73soh446nw/z2hgh7ue6493kltz/d3d3Lmp1c3RpbndlbHNoLm1lL25ld3NsZXR0ZXIvbWlzc2luZy1zb21lb25l ) / Read time: 4 minutes The Saturday Solopreneur is brought to you by: Free: Grow Your Business By Writing (4 simple steps) ---------------------------------------------------- Do you want to become a writer? Kieran Drew attracted 250k readers and made $1.5m in 4 steps. Get his exact roadmap here: Read the guide ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh69wlq2tquqwoxk73soh446nw/qvh8h8udw7grvvsg/aHR0cHM6Ly9nby5raWVyYW5kcmV3LmNvbS9td3ItY3Mv ) Solopreneur CPA Firm -------------------- Echie CPA: your all-in-one accounting solution. For solopreneurs, by a solopreneur. Learn more about how Kenneth can help. Pay Uncle Sam Less! ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh69wlq2tquqwoxk73soh446nw/qvh8h8udw7grvvsg/aHR0cHM6Ly9lY2hpZWNwYS5jb20v ) By the summer of 2021, I was two years into my solopreneur journey. And I flew from Nashville to Santa Monica to meet my old bosses, Luke and Travis, the guys who started PatientPop. I'd stayed on as an advisor, and over the previous few weeks, we'd been texting a lot about a real problem the business was facing. The pandemic had shaken up business quite a bit. Doctors had pivoted to telehealth almost overnight, and PatientPop's physician customers needed something different from what the product was originally built to do. I ate up the challenge, and jamming with Luke and Travis was stimulating my sales and marketing brain in a way I hadn't felt in years. I love these guys, and the problem was interesting. At some point, somebody made a joke about me coming back to run the new thing, and we all laughed. But then, the texts got more serious. And they eventually asked if I'd meet up in person. So there I was at the Fairmont Hotel in Santa Monica, waiting for Luke, just like old times. I even snagged a seat at our favorite table outside. And the moment I saw him, I felt it. The energy of working on a big, challenging problem with people I trusted. The feeling of being a people leader and a part of something bigger than just me. I'd spent the past couple of years alone in my home office, grinding away on my business, and I'd forgotten how addicting the feeling of teamwork and camaraderie can be. The energy that comes from being a part of something big and special. I left the meeting totally lit up and proceeded to tell my wife everything I missed about my old career. She listened patiently, and I could see she was choosing her words carefully. --------------- She was worried --------------- Jennifer remembers things about me that I delete from my own memory bank. How things made me feel (and behave). She knows what happens when I get lost in work where other people depend on me, and I have to depend on other people. Where goals are big, targets come with excruciating pressure, and board members don't mess around being nice. In that kind of environment, I grind myself down to the nub. Because I'm terrified of failure, or worse, disappointing people I respect. The idea of something not going great on my watch is a situation I'll work to avoid at any cost. So I push until I'm physically and mentally worn out, and Jennifer has seen it enough to know the whole story before it starts. So she worried I was seeing this opportunity through rose-colored glasses. Couldn't I remember how burned out I was when I left? But I wasn't ready to hear that. So I went back to the company for eight months, continuing my own online business in tandem. While we launched telehealth and made a big splash in the market and got the P&L looking good, something was off. And it felt that way almost from the start. The company was amazing, and the people were fantastic. But the version of Justin I'd been missing wasn't in me anymore. I wasn't excited about doing the actual work. I was excited about the identity. The CRO title. The steady income. The ability to coach and lead a team of all-stars. The C-suite bio. The invitations to speak at SaaS events and popular podcasts. All the stuff that sounds impressive, and feels especially important when you don't have it anymore. But when I got back into the beast, I realized that none of those things actually make me happy. I'd moved on to building my own thing, to the freedom of controlling my days, to not having to ask anyone for permission for anything. I'd undervalued those freedoms when I was sitting alone in my home office, feeling isolated. I realized I'd focused on what I was missing instead of what I had. And when I returned to just running my own business, it was the most relieved I'd ever felt. ---------------- What I got wrong ---------------- It took me a long time to understand what had actually happened here. Because those feelings at The Fairmont Hotel were genuine. The pull was real, and my excitement was undeniable. But I never stopped to ask myself a simple question: Why do I actually want this? Not "Do I want this?" That second question is too easy to answer when you're caught up in a moment. The better question is why? And if I'd explored that, the answer would have been uncomfortable, but obvious. I didn't really want that job. I wanted that title. I didn't miss the work. I missed the identity of being an important C-suite exec in tech. I was trying to go back to a version of myself that was long gone. Looking back, I should have seen that coming. I've learned that I basically have a five-year shelf life for work. I spent five years in pharma and med devices, five years at ZocDoc, and five years at PatientPop. And every time a five-year anniversary starts creeping up, I get itchy. Itchy for something new, and I start feeling like a different person than the one I was at the beginning of that particular journey. Going back to PatientPop wasn't a return to something I truly longed for. It was me trying to be someone I'd outgrown. ---------------- Why this matters ---------------- A buddy of mine runs a small SaaS company in London. A few years ago, he spent 12 months and a lot of money buying out an unsavory business partner. It was a miserable experience, but when it was over, he owned 100% of his company, and that satisfied him. Then, just a year into full ownership, he started to consider bringing someone else into the business. A new partner with a new equity split. He was ready to give away a huge piece of this thing he'd spent all that time and energy and money fighting to gain ownership of. And when he finally stopped to ask himself why, the answer had nothing to do with needing a partner. He realized he was just lonely. He felt isolated sitting alone in his house, running his business. He missed having someone to talk through problems with, someone to share the weight of bad decisions, and the success of good ones. But he didn't need to give up equity and ownership to fix that problem. He ended up hiring a developer and a sales guy. He kept his ownership and suddenly had smart people to work with every day. Celebrations were better, tough times had more support, and the pull to bring on a partner disappeared over time. My buddy almost made a costly mistake because he confused being lonely with needing a co-founder. The feeling was real, but he was misinterpreting the signals. That's something we should all pay attention to. The pull always feels urgent and real, and sometimes it is. But the only way to know what it really means is to stop and ask yourself why you're actually considering the thing. Not whether you want it. But why. Because "I'm lonely" is very different than "I need a partner." And "I miss feeling important" is very different from "I miss the actual work." --------------- The bottom line --------------- I hit this same crossroads again recently when I discontinued my two most popular courses, The LinkedIn OS and Content OS. In doing that, I parted ways with about 75% of my typical monthly revenue. And wouldn't you know it, a few weeks after I shut it all down, I felt that familiar pull to bring them back. They made great money. It was a proven model. There were millions of dollars a year just sitting there waiting for me. But this time, I knew the right question. Why do I want this? And the answer was that I missed the money and the safety net. But I didn't want to be the guy who teaches people how to use LinkedIn or write content. That's why I discontinued these products in the first place. My five-year itch has me going in a new direction. I was just yearning for the comfort of a stage I've outgrown. And, as David Brooks would say, I'm looking for my "second mountain." I want mine to be built around creative impact, getting better at things I'm bad at, and doing work that challenges me instead of feeling monotonous. I want to continue writing counterintuitive ideas on earning money, reclaiming your time, and building a life you choose. I'm leaning into a new identity as a writer who asks challenging and interesting questions about life and business, and somebody who definitely doesn't have all of the answers but stays curious. So here's my question for you today: Is there something from your past that's pulling at you right now? And if you stop to ask yourself why you actually want it, what does your honest answer tell you? If you're up for sharing, reply and tell us. While we can't reply to everyone, Jennifer and I love reading every response that comes our way. That's all for this week. See you next Saturday. Justin Welsh Find me on X ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh69wlq2tquqwoxk73soh446nw/g3hnhwum9d73nof3/aHR0cHM6Ly90d2l0dGVyLmNvbS90aGVqdXN0aW53ZWxzaC8= ), LinkedIn ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh69wlq2tquqwoxk73soh446nw/wnh2h6uq759w4qil/aHR0cHM6Ly93d3cubGlua2VkaW4uY29tL2luL2p1c3RpbndlbHNoLw== ), Instagram, ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh69wlq2tquqwoxk73soh446nw/m2h7h6u35gk895sl/aHR0cHM6Ly93d3cuaW5zdGFncmFtLmNvbS90aGVqdXN0aW53ZWxzaC8= ) or Book a 1:1 Call ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh69wlq2tquqwoxk73soh446nw/x0hph3ue2r8wzmfg/aHR0cHM6Ly9pbnRyby5jby9KdXN0aW5XZWxzaA== ) Join 10K+ entrepreneurs in my business Masterclass: --------------------------------------------------- The Creator MBA Masterclass ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh69wlq2tquqwoxk73soh446nw/58hvh8ugxvpmovs7/aHR0cHM6Ly9sZWFybi5qdXN0aW53ZWxzaC5tZS9jcmVhdG9yLW1iYS1tYXN0ZXJjbGFzcy8_Y291cG9uX2NvZGU9Q01CQTIwMjZGTEFTSFNBTEU= ) is my complete business playbook. Every framework and system I used to grow my following to 1.5M and my business to $12M in revenue at 90% margins. Learn how to finally monetize your expertise! Your Email Preferences: Your email address is b@email.gomodulr.com Change your account details ( https://preferences.convertkit-mail4.com/o8unwm0plofqh69wlq2tquqwoxk73soh446nw )↗ ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh69wlq2tquqwoxk73soh446nw/25h2h9u39vr208b8/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) Unsubscribe from all emails ( https://b9bcc769.unsubscribe.convertkit-mail4.com/o8unwm0plofqh69wlq2tquqwoxk73soh446nw )↗ ( https://b9bcc769.click.convertkit-mail4.com/o8unwm0plofqh69wlq2tquqwoxk73soh446nw/25h2h9u39vr208b8/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) 30 Main Street PO Box 448, Accord, NY 12404-9998

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Missing someone who doesn’t exist.

hello@justinwelsh.me3/14/2026

Kit

* * * ******************* I'm a crazy person. ******************* Read on my website ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpl9versqu6mrrk74t5hnnlkr/48hvh7umv4w4k3aq/aHR0cHM6Ly93d3cuanVzdGlud2Vsc2gubWUvbmV3c2xldHRlci9jcmF6eS1wZXJzb24= ) / Read time: 4 minutes The Saturday Solopreneur is brought to you by: Meet Your First AI Employee --------------------------- It joined Monday. By Tuesday it had done more than your last three hires combined. No onboarding. No complaints. Try Emika for Free ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpl9versqu6mrrk74t5hnnlkr/wnh2h6uqneme8ztl/aHR0cHM6Ly9lbWlrYS5haS8_dXRtX2NhbXBhaWduPWp3ZWxzaCZ1dG1fc291cmNlPWp3ZWxzaF9lbWFpbA== ) Learn how to Build and Earn Using AI - here's how ------------------------------------------------- Join Outskill’s 2-Day LIVE AI Mastermind to build automations, create AI agents & learn to monetize AI with 10M+ learners. Start learning now! ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpl9versqu6mrrk74t5hnnlkr/wnh2h6uqneme8ztl/aHR0cHM6Ly9saW5rLm91dHNraWxsLmNvbS9KVVNUSU5XRUxNQVIy ) A buddy who used to work for me just had his first baby a few months ago. Jennifer and I met him and his wife out at a winery when the baby was just seven weeks old. It was a beautiful Saturday afternoon, and we were so happy (and pleasantly surprised) that our friends were up for some socializing with a newborn in the picture. They showed up a bit late after struggling to get the baby to eat. And my friend looked tired as his eyes darted between our conversation and the baby every few seconds. When I asked how he was sleeping, he laughed and said it's about three hours a night. But here he was. Out on a Saturday, newborn in tow, making time to be a good friend on top of everything else. He told me he wakes up at 4 a.m. to help with the baby, get the house moving, and fit in a workout before he heads to work. He runs revenue at an early-stage AI company in the Bay Area. I hired this guy almost a decade ago. And right when I met him, I knew he had something most people don't. A gear that doesn't turn off. Watching him describe his life now, I realized he couldn't slow down, even if he wanted to. His family needs him. His company needs him. And the version they need is the one that does everything at 100%, all the time, no exceptions. Sounds exhausting, I know. But I'm not worried about my friend. Because I recognize him. ---------- The mirror ---------- When people ask my wife to describe me, she says (without fail), "He's a crazy person." She doesn't mean it as an insult, but more like a doctor giving a diagnosis. Something she's observed over the years about my personality and finally accepted and stopped trying to fix. Jennifer's not wrong. I'm a control freak who obsesses over my work. When a day goes poorly, I can't let it go. I'll fixate on whatever went wrong until I figure out how to make sure it won't happen again. And even though I know every business has ebbs and flows, I'm not good with ebbs. I need every day to go as planned, and I have a hard time letting anything get in the way of that. A few weeks ago, I had a piece of important content scheduled to go out at 4:48 a.m. Pacific Time. That's when I've released content for six years. But normally I'm on East Coast time, so it's much easier to manage. But here I am in California, so I woke up at 4:00 a.m. Not because I set an alarm. Because my brain wouldn't let me sleep. I was too wired, thinking about this content existing out in the world without me being there to make sure it went well. So I lay there awake in the dark, waiting, and grabbed my phone the second it went live. But here's the thing (in defense of my crazy): The obsession that wakes me up at 4 a.m. to micro-manage social media is the same obsession that built this business in the first place. The perfectionism that drives Jennifer nuts is the same perfectionism that keeps my open rates above 60% with 180,000+ weekly newsletter readers. My inability to let a bad day go is the reason my business has improved for six years straight. I can't separate the flaw from the fuel. They're the same thing. ----------- The pattern ----------- It's not just my buddy with the new baby and me who are wired like this. I see crazy people all over the place when I study successful folks. I have a founder friend in Austin who checks his Stripe dashboard before he checks on his kids in the morning. Because he physically can't start his day without knowing his numbers. Sure, the business wouldn’t change if he just skipped it for a day, but he needs to know if there’s a problem immediately. Like the moment his eyes open. Sounds crazy to most, but to me it sounds totally normal. Successful people like him don't have better habits than everyone else. In fact, they probably have something a bit wrong with them, by average standards anyway. A weird compulsion, or an inability to do things at 70%, or an engine that runs hot whether they want it to or not. People will (admiringly) roll these personality quirks into terms like "determination" and "grit." They've "got strong priorities," "rigid boundaries," and "disciplined morning routines." But the people I know who are like this? Most of them aren’t as disciplined as they are obsessed. They have a monster chip on their shoulder that never went away, or an inability to be satisfied, even when they've hit every milestone on the dashboard. From the outside, it looks like ambition, but on the inside, it feels more like an addiction. And I used to think these kinds of people succeeded, despite the thing that was off about them. But now I think they succeed because of it. They can't separate the flaw from the fuel either. -------- The cost -------- There's a huge toll to pay for these kinds of behaviors, and that darker side doesn't get talked about much, especially on social media. Because most people will notice the success part without imagining what it takes to get there. People congratulate me on my business all the time. But my mood often swings like a pendulum based on how my work is going. A newsletter that underperforms can wreck a Saturday, while one that everyone loves makes me feel invincible. And when my content bombs for days on end, I can easily convince myself that everything around me is crashing down. When I'm being logical, I know to zoom out and look at the big picture instead of any singular event. But I can't help it. I rise and fall with the daily numbers, and I struggle to insert logic into situations that could threaten everything I've worked so hard for. There's a physical cost to this behavior, too. I carry around intense stress, struggle to relax, lie in bed overthinking things at night, and worry about work during moments I should be fully present with Jennifer. A few months ago, she looked at me after a particularly rough week. She put both her hands on my cheeks and looked me in the eyes. Not as a casual check-in, but the way you ask when you're scared of what the answer’s going to be. I said I was fine. We both knew it wasn't true. She kept her hands on my face for a moment, and we just sat there quietly. I didn't feel better exactly, but I certainly felt a little less alone in the moment. At the end of the day, I chose to build this business. I love the work I've created for myself. And I love how I'm wired. But obsession costs something. It always does. Sometimes I wonder if I would trade this crazy personality for an easier-going one if I could. Someone who lets things go, or has a bad day and shrugs it off. Someone who operates at 70% and sleeps fine anyway. My answer is still no. But it used to come easier. --------------- The bottom line --------------- Jennifer will forever call me a crazy person. And we both finally get that my crazy is tangled up with everything else, that you can't extract it without losing something important. So now we just try to pay attention to where the crazy is focused, and we (usually) make the most of it. So here's something that might be worth pondering this week: Do you have something slightly wrong with you? A compulsion you can't turn off? An obsession you've learned to aim at something productive? If so, I'd love to hear about it. Tell me what it costs you, and what it's built. I'm inviting you to help me feel a little less crazy. Or maybe by knowing my story, you can feel a little less crazy about yourself. While we can't reply to every email we get, we love reading your responses. And that's all for this week. See you next Saturday. P.S. If you're interested in aiming that obsessive kind of behavior at growing your audience and building your first online business, check out my masterclass, The Creator MBA ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpl9versqu6mrrk74t5hnnlkr/n2hohquvmz2zelc0/aHR0cHM6Ly9sZWFybi5qdXN0aW53ZWxzaC5tZS9jcmVhdG9yLW1iYS1tYXN0ZXJjbGFzcy8_Y291cG9uX2NvZGU9Q01CQTIwMjZGTEFTSFNBTEU= ). You'll learn to build a profitable offer, get attention online, create automated funnels, and generate income for yourself. Justin Welsh Find me on X ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpl9versqu6mrrk74t5hnnlkr/reh8h9um4gkgk9h6/aHR0cHM6Ly90d2l0dGVyLmNvbS90aGVqdXN0aW53ZWxzaC8= ), LinkedIn ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpl9versqu6mrrk74t5hnnlkr/08hwhgu2v3n3nobp/aHR0cHM6Ly93d3cubGlua2VkaW4uY29tL2luL2p1c3RpbndlbHNoLw== ), Instagram, ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpl9versqu6mrrk74t5hnnlkr/8ghqh3uozmwmw2il/aHR0cHM6Ly93d3cuaW5zdGFncmFtLmNvbS90aGVqdXN0aW53ZWxzaC8= ) or Book a 1:1 Call ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpl9versqu6mrrk74t5hnnlkr/vqh3hmuolzmzm4fw/aHR0cHM6Ly9pbnRyby5jby9KdXN0aW5XZWxzaA== ) Join 10K+ entrepreneurs in my business Masterclass: --------------------------------------------------- The Creator MBA Masterclass ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpl9versqu6mrrk74t5hnnlkr/n2hohquvmz2zelc0/aHR0cHM6Ly9sZWFybi5qdXN0aW53ZWxzaC5tZS9jcmVhdG9yLW1iYS1tYXN0ZXJjbGFzcy8_Y291cG9uX2NvZGU9Q01CQTIwMjZGTEFTSFNBTEU= ) is my complete business playbook. Every framework and system I used to grow my following to 1.5M and my business to $12M in revenue at 90% margins. Learn how to finally monetize your expertise! Your Email Preferences: Your email address is b@email.gomodulr.com Change your account details ( https://preferences.convertkit-mail4.com/4zu9eg03ozsehpl9versqu6mrrk74t5hnnlkr )↗ ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpl9versqu6mrrk74t5hnnlkr/l2heh6ule8q8qvtg/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) Unsubscribe from all emails ( https://b9bcc769.unsubscribe.convertkit-mail4.com/4zu9eg03ozsehpl9versqu6mrrk74t5hnnlkr )↗ ( https://b9bcc769.click.convertkit-mail4.com/4zu9eg03ozsehpl9versqu6mrrk74t5hnnlkr/l2heh6ule8q8qvtg/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) 30 Main Street PO Box 448, Accord, NY 12404-9998

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I'm a crazy person.

hello@justinwelsh.me3/7/2026

Kit

* * * *************** Bored to death. *************** Read on my website ( https://b9bcc769.click.convertkit-mail4.com/lmulpxw2g3imhnedddoigu8vnp2lwsgh22vm9/dphehmuevvmv6dtl/aHR0cHM6Ly93d3cuanVzdGlud2Vsc2gubWUvbmV3c2xldHRlci9ib3JlZA== ) / Read time: 4 minutes At some point in the last few years, I got really good at my job. I don't say that to brag. I say it because “getting good at something” is everybody’s goal, but people rarely talk about what happens after that. By early 2022, I had most things in my business firing on all cylinders. I’d figured out how to create content that resonated, how to generate leads for my products, how to collect information about my leads, how to make sales with custom pitches, and how to do all of that on repeat. Revenue was predictable, and I could log into my Kajabi dashboard at 8 am, noon, and 4 pm and tell you almost down to the dollar where the numbers would be. That's supposed to be the dream, right? Predictable, repeatable income from an automated process. But I can remember sitting at my desk one morning, coffee in hand, looking at the 8 a.m. revenue and feeling numb to the numbers. Not ungrateful or disappointed. I know how fortunate I’ve been. But somewhere along the way, my calendar started to feel more like an assembly line than a creative endeavor. I was going through the same motions and producing the same outputs. The creative parts of my work that once lit me up had completely disappeared. The boring kind of burnout -------------------------- You might assume folks lose motivation because something goes wrong. Their businesses failed, or the market shifted, or something “bad happened.” But there’s a version of burnout that’s less common (or at least talked about less). The version where everything’s pretty much fine, numbers are as good as ever, and you’re just bored out of your mind. This happens in all kinds of jobs. My friend Jason is a financial advisor who spent ten years building his firm, and he can do the job in his sleep. It’s paying the bills, and he goes on great vacations. But he doesn’t enjoy the work anymore. Hell, I spent years selling to physicians who wanted to grow their practices for financial reasons, but didn’t even love seeing patients. Sure, money and success are important. But monotony is poison for the spirit. You get good at the things that make your business succeed. But reaching that level kills some part of the work that makes things interesting. And then, there you are, going through the motions, day in and day out. And feeling guilty about not liking it anymore. I was thinking about that as I read my buddy Brad Stulberg’s new book, The Way of Excellence ( https://b9bcc769.click.convertkit-mail4.com/lmulpxw2g3imhnedddoigu8vnp2lwsgh22vm9/9qhzhdud00l0w6bz/aHR0cHM6Ly93d3cuYW1hem9uLmNvbS9XYXktRXhjZWxsZW5jZS1HcmVhdG5lc3MtU2F0aXNmYWN0aW9uLUNoYW90aWMvZHAvMDA2MzM4NTk0NQ== ) (not surprisingly, an excellent book). He talks about how when you're early in some sort of journey, the progress itself keeps you going. You're getting better every day, and you can feel it. But eventually progress levels off, and the honeymoon fades. We call that “being able to do this in your sleep.” The people who keep going after that are the ones who fall in love with the joy of their craft and the people they do it with. That hit me because I’m one of those people who almost didn't make it through the honeymoon. 500 replies ----------- Deep into 2025, my assembly line was humming along fine. I was writing about the usual topics my audience expected: solopreneurship, reverse engineering social media, selling products, and the new trend, AI. Those topics are all fine, and that tactical stuff performed well enough. But my work was feeling less like “the real me” with every new issue. I think back to when I started doing this work. The dozens of people building alongside me on LinkedIn and Twitter. Most of them are gone now. They burned out, or got jobs, or took a break, and I just never saw them in my feed again. I doubt any of them “failed” in the traditional sense. I think the honeymoon phase just expired, and they didn't find a way through it. And I felt myself being pulled in the same direction. Then, I wrote a newsletter that was different from what I’d been publishing. It was about how I'd spent twelve months pretending I’d eventually organize my garage ( https://b9bcc769.click.convertkit-mail4.com/lmulpxw2g3imhnedddoigu8vnp2lwsgh22vm9/reh8h9um44e4dqh6/aHR0cHM6Ly93d3cuanVzdGlud2Vsc2gubWUvbmV3c2xldHRlci9mdXR1cmUteW91 ), when I was never actually going to do it. It’s about deferring decisions and the things we push to "someday.” That newsletter issue didn’t have much to do with social media strategy, pricing, or solopreneurship. Not on the surface, at least. It was personal, a bit philosophical, and kind of uncomfortable to share out loud. I was nervous about how it might land with my readers. My newsletters up until then had averaged around 45 replies per issue. And that particular issue got over 500 replies! And they weren't the usual "Great tips, thanks." kind of responses. Readers penned heartfelt paragraphs. They told me things they’d never told anyone, treating the reply to me like a journal. People said I’d made them rethink decisions they'd been sitting on for years. I’m back again -------------- I loved writing that newsletter, and my audience was asking for more. I honestly hadn't felt that combination in a long time. It wasn’t necessarily a lightbulb moment, but more like a jolt of creative energy I hadn't experienced in so long. I hadn't shared the issue with Jennifer beforehand, which is unusual in our process. She hadn’t seen it before it came out, and I remember her reading it and walking into my office. She said something like "I love the new issue, but it's sort of different from what you've been writing. But different in a good way." And that was it. Jennifer didn't ask about why or what I was writing about next. She was commenting about the energy she could feel from it. I felt back again. When she edited the next issue, she liked the direction again. "More fun to read than the tactical stuff." That’s when I admitted I wasn’t feeling the tactical stuff anymore. I want to write about the intersection of life and business, or whatever you call these essays. This detour might not generate the same revenue (it doesn’t), but it’s what lights me up these days. So I’m going there. A trade that’s worth it ----------------------- When I decided to walk through a new door, business was fine. The stuff I was supposed to care about was humming along. But I felt like I was losing my craft. My assembly line had chewed it up and spit it out, and I wasn’t excited to get out of bed anymore. The thing that saved me wasn't optimizing that machine or grinding harder through the boredom of “staying on brand,” or outsourcing it to a bunch of employees. What saved me was letting go of the stuff that made strategic sense on paper, and writing what I really cared about instead. That's what success over the long run is really about, I think. Maybe not in the early stages where everything is exciting, and the growth feels electric. But the part after that. The part where you have to find a different reason to keep going. The part where the only reason that actually works is caring about the work itself. I’ve given away a lot of revenue by venturing away from solopreneur tactics. But in exchange, I love to sit down and write again. Working on this newsletter is a pleasure every week. And hearing back from so many readers is a real “wow” factor. You wouldn’t believe the personal stories people share with us. Moving, interesting, inspirational, and even embarrassing stories. Reading your replies has become a big part of our newsletter process that we love most. And I can tell you that didn’t happen when I was writing about social media and landing pages. The bottom line --------------- I could still be running the assembly line. The numbers were good, the system was working, and nobody was asking me to change. But I think I would have become one of those people who quietly disappeared. Eventually, I would have given in to work I wasn’t excited about. If you've been doing something long enough that you've mastered it, and the mastery feels more like a trap than an achievement, that's probably worth paying attention to. The thing that got you here, the challenge, the curiosity, the figuring-it-out stuff, might need to come from a new place now. I’m very systems-oriented, and I still have an assembly line, of sorts. I just stopped letting it dictate what I make. So here's my question for today: Where have you lost the creative spark in your life or business? And what could it look like to bring raw creativity back? Reply and tell me. While I can't reply to everyone, Jennifer and I read every response, and we love hearing from you. That's all for this week. See you next Saturday. Justin Welsh Find me on X ( https://b9bcc769.click.convertkit-mail4.com/lmulpxw2g3imhnedddoigu8vnp2lwsgh22vm9/x0hph3ueoolo25ug/aHR0cHM6Ly90d2l0dGVyLmNvbS90aGVqdXN0aW53ZWxzaC8= ), LinkedIn ( https://b9bcc769.click.convertkit-mail4.com/lmulpxw2g3imhnedddoigu8vnp2lwsgh22vm9/25h2h9u366e695c8/aHR0cHM6Ly93d3cubGlua2VkaW4uY29tL2luL2p1c3RpbndlbHNoLw== ), Instagram, ( https://b9bcc769.click.convertkit-mail4.com/lmulpxw2g3imhnedddoigu8vnp2lwsgh22vm9/g3hnhwumrrkrwdh3/aHR0cHM6Ly93d3cuaW5zdGFncmFtLmNvbS90aGVqdXN0aW53ZWxzaC8= ) or Book a 1:1 Call ( https://b9bcc769.click.convertkit-mail4.com/lmulpxw2g3imhnedddoigu8vnp2lwsgh22vm9/n2hohquvmmkm05u0/aHR0cHM6Ly9pbnRyby5jby9KdXN0aW5XZWxzaA== ) Join 10K+ entrepreneurs in my business Masterclass: --------------------------------------------------- The Creator MBA Masterclass ( https://b9bcc769.click.convertkit-mail4.com/lmulpxw2g3imhnedddoigu8vnp2lwsgh22vm9/48hvh7umvvnv8ntq/aHR0cHM6Ly9sZWFybi5qdXN0aW53ZWxzaC5tZS9jcmVhdG9yLW1iYS1tYXN0ZXJjbGFzcy8_Y291cG9uX2NvZGU9Q01CQTIwMjZGTEFTSFNBTEU= ) is my complete business playbook. Every framework and system I used to grow my following to 1.5M and my business to $12M in revenue at 90% margins. Learn how to finally monetize your expertise! Your Email Preferences: Your email address is b@email.gomodulr.com Change your account details ( https://preferences.convertkit-mail4.com/lmulpxw2g3imhnedddoigu8vnp2lwsgh22vm9 )↗ ( https://b9bcc769.click.convertkit-mail4.com/lmulpxw2g3imhnedddoigu8vnp2lwsgh22vm9/8ghqh3uozzxznohl/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) Unsubscribe from all emails ( https://b9bcc769.unsubscribe.convertkit-mail4.com/lmulpxw2g3imhnedddoigu8vnp2lwsgh22vm9 )↗ ( https://b9bcc769.click.convertkit-mail4.com/lmulpxw2g3imhnedddoigu8vnp2lwsgh22vm9/8ghqh3uozzxznohl/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) 30 Main Street PO Box 448, Accord, NY 12404-9998

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Bored to death.

hello@justinwelsh.me2/28/2026

Kit

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Get out.

hello@justinwelsh.me2/21/2026

Kit

* * * ************ Rock bottom. ************ Read on my website ( https://b9bcc769.click.convertkit-mail4.com/d0umk08qr7a0hov868quluz22r244slhkk3e9/25h2h9u36g33m3f8/aHR0cHM6Ly93d3cuanVzdGlud2Vsc2gubWUvbmV3c2xldHRlci9yb2NrLWJvdHRvbQ== ) / Read time: 4 minutes The Saturday Solopreneur is brought to you by: Free: Grow Your Business By Writing (4 simple steps) ---------------------------------------------------- Do you want to become a writer? Kieran Drew attracted 250k readers and made $1.5m in 4 steps. Get his exact roadmap here: Read the guide ( https://b9bcc769.click.convertkit-mail4.com/d0umk08qr7a0hov868quluz22r244slhkk3e9/qvh8h8udzvddkohg/aHR0cHM6Ly9nby5raWVyYW5kcmV3LmNvbS9td3ItY3Mv ) Last Sunday, I watched a 30-year-old American woman throw herself down a mountain at 70 miles per hour. It just happened to be the same mountain that nearly ended her career four years ago. Breezy Johnson won the gold in the women's downhill by four one-hundredths of a second, securing Team USA's first medal of this year's Olympics. Most of the coverage has been about Lindsey Vonn, who crashed violently during the same race, broke her leg, and got airlifted off the course. And I get it. The Vonn story is dramatic, and she's probably the greatest of all time. But, to me, the bigger story is about the woman who won. I'm not going to pretend I'm some big downhill skiing fan. I'm definitely not. I watch it during the Olympics like most people, and then I forget about it for another four years. But I started reading about what Breezy Johnson went through to get back to that starting gate, and it’s pretty incredible. It definitely took guts. But I don't think "guts" is the actual story here. The Breezy injury saga ---------------------- Breezy tore her ACL in 2018. She came back from that, and while rehabbing, blew out the other knee the following year. She was away from the sport for twenty-two months. Two major knee injuries, one on each leg, before she even turned 25. She came back anyway. And when she did, she was the best skier she'd ever been, eventually working her way up to the number two ranking in the world. As she stacked up podium finishes, everyone expected her to medal at the upcoming 2022 Beijing Olympics. Then, a few weeks before the Games, she crashed during a training run in Cortina. The same Cortina mountain where she just won gold last week. Tore up her knee again and had to withdraw from the Olympic team. And then the setbacks just piled on. She got hit with a 14-month competition ban for missed drug tests. She didn't test positive. She missed them and says it was an administrative error. It doesn't really matter much when your name is being bashed in the headlines while you're sitting at home watching everyone else race for another full season. Breezy has been open about her struggles with depression and anxiety through all of this. Knees heal eventually, but watching your competitors race while your career feels like it's evaporating is a situation there is no surgery for. Any one of those setbacks would be a reasonable place for a normal person to quit. But that’s when she decided to rearchitect everything from her brain down. What she did differently ------------------------ When she came back this time, she didn't go through the same rehab and return to the same training programs she’d gone through before. She started over. Completely. She got into something called neurocognitive rehabilitation, which, to be honest, I had to look up. Instead of just fixing her knees and getting back on the slopes, she retrained how her brain talks to her body at high speed. How she sees, reacts, and makes decisions at 70 miles per hour. She trained from the brain down instead of from the knees up. Same name. Same team. Same sport. Same mountain. But a completely different person standing at the top of it. Breezy 2.0. And she wasn't even perfect last Sunday. She got "off her line" during the run and still won because she was attacking so aggressively that she could absorb mistakes. That's what a rebuild gives you. Perfection wasn't the point. Margin was. Breezy said something interesting after the race: "People are jealous of people with Olympic gold medals. They're not necessarily jealous of the journey it took to get those medals." That's been rattling around in my head all week. This reminded me of my buddy, Scott Barker. He’s also on a journey of tearing everything up to rebuild from the brain down. But his rebuild looks a bit different than Breezy's. Scott ----- Breezy rebuilt herself to get back on the same mountain, but Scott realized he was on the wrong mountain entirely. Scott co-founded a venture capital fund called GTMfund and spent four and a half years grinding to build it. Before that, Scott had worked building the #1 podcast focused on sales engagement, SalesHacker, and then turned that into several key leadership roles at Outreach. He went fifteen years of going non-stop, pushing for the next milestone. And as soon as he'd hit one, he'd move the goalpost. During those years building the fund, Scott looked like the picture of success. But his personal life was falling apart at the seams. He proposed to his girlfriend, but their engagement fell through. His grandfather died. He ended up in the emergency room in Italy with an ulcer. He coped with alcohol. And he eventually endured weekly panic attacks. As his personal life deteriorated, he couldn’t process any of it. Work was his sole priority. He signed off every email with “#50MOD,” meaning “50 Million Or Die” (the fundraising target), and he meant it quite literally. Scott realized something had to change. But he couldn’t stop working. So, he hired a therapist, a performance coach, and a spiritual advisor. All three at the same time, just to keep the train on the tracks. But he was trying to heal with the same intensity he applied to everything else. That kept him in the game for a little while, but it didn't actually fix anything. Eventually, the train came off the tracks entirely when he stopped sleeping. He was down to just two or three hours a night, and he barely recognized himself in the mirror. So he finally hit pause, took a leave of absence from the fund, and gave himself space for the first time in his adult life. That's when he realized he had no idea who he was if he wasn't achieving things. Achievement had become his whole identity. And that identity had made him miserable. The life he had dreamed of for so long felt empty and meaningless. So Scott left his job, sold everything he owned, and headed East to learn something about himself that fifteen years of winning never taught him. He writes about this in his newsletter, The Wake Up Call ( https://b9bcc769.click.convertkit-mail4.com/d0umk08qr7a0hov868quluz22r244slhkk3e9/kkhmh2unrennx8ak/aHR0cHM6Ly90aGV3YWtldXBjYWxsbmV3c2xldHRlci5zdWJzdGFjay5jb20v ). When Scott shared his full story with me, I read it out loud to Jennifer. I had to stop a few times because I got emotional. Not because it was sad. Because I recognized more of myself in Scott’s story than I was comfortable with. The relentless pushing, the moving goalposts, the identity wrapped up in achievement. I'm not in Scott's situation, and I love what I do, but reading his words was like looking in a mirror and not loving everything I saw. Different paths for different people ------------------------------------ Most people hear these two stories and figure out pretty quickly which one they relate to. You're either Breezy, rebuilding to come back stronger at the same game. Or you're Scott, rebuilding because you realize that you want to play a different game entirely. But there's a third version that I think most people don't consider. You start rebuilding, thinking you're Breezy, planning to come back to the same game stronger than ever. But somewhere in the process, you realize you're actually Scott. The rebuild reveals that the mountain you've been climbing isn't actually your mountain at all. It doesn't matter which version you are. At some point, most of us need to be rearchitected from the ground up to keep moving forward. Some of us will come back to the same race. Some of us will find a new one. And some of us won't know which one we are until we're already in the middle of it. The bottom line --------------- Breezy won Gold on the same mountain where her career nearly ended. And Scott walked away from a mountain he'd been climbing for fifteen years. Both of them are better for it. So here's the questions I’d love for you to consider this week: If you’re confident you’re on the right mountain, do you have the right plan in place, brain-down, to keep going successfully? Or do you need to accept that the mountain you’re flying down isn’t the right mountain for you at all? Reply and tell us. While we can't reply to everyone, Jennifer and I read every response, and we love hearing from you. That's all for this week. See you next Saturday. P.S. If you're confident you're on the right mountain but need some direction, consider checking out my masterclass, The Creator MBA ( https://b9bcc769.click.convertkit-mail4.com/d0umk08qr7a0hov868quluz22r244slhkk3e9/58hvh8ugq0gg6ma7/aHR0cHM6Ly9sZWFybi5qdXN0aW53ZWxzaC5tZS9jcmVhdG9yLW1iYS1tYXN0ZXJjbGFzcy8_Y291cG9uX2NvZGU9Q01CQTIwMjZGTEFTSFNBTEU= ). I'll help you validate you have the right idea, select the most profitable offer, attach it to the most impactful funnel, and then automate the majority of it. Start watching The Creator MBA now. ( https://b9bcc769.click.convertkit-mail4.com/d0umk08qr7a0hov868quluz22r244slhkk3e9/58hvh8ugq0gg6ma7/aHR0cHM6Ly9sZWFybi5qdXN0aW53ZWxzaC5tZS9jcmVhdG9yLW1iYS1tYXN0ZXJjbGFzcy8_Y291cG9uX2NvZGU9Q01CQTIwMjZGTEFTSFNBTEU= ) Justin Welsh Find me on X ( https://b9bcc769.click.convertkit-mail4.com/d0umk08qr7a0hov868quluz22r244slhkk3e9/g3hnhwumrnmmqpc3/aHR0cHM6Ly90d2l0dGVyLmNvbS90aGVqdXN0aW53ZWxzaC8= ), LinkedIn ( https://b9bcc769.click.convertkit-mail4.com/d0umk08qr7a0hov868quluz22r244slhkk3e9/9qhzhdud0xdd5niz/aHR0cHM6Ly93d3cubGlua2VkaW4uY29tL2luL2p1c3RpbndlbHNoLw== ), Instagram, ( https://b9bcc769.click.convertkit-mail4.com/d0umk08qr7a0hov868quluz22r244slhkk3e9/3ohphdu30r33pxap/aHR0cHM6Ly93d3cuaW5zdGFncmFtLmNvbS90aGVqdXN0aW53ZWxzaC8= ) or Book a 1:1 Call ( https://b9bcc769.click.convertkit-mail4.com/d0umk08qr7a0hov868quluz22r244slhkk3e9/n2hohquvmgvv7mb0/aHR0cHM6Ly9pbnRyby5jby9KdXN0aW5XZWxzaA== ) Join 10K+ entrepreneurs in my business Masterclass: --------------------------------------------------- The Creator MBA Masterclass ( https://b9bcc769.click.convertkit-mail4.com/d0umk08qr7a0hov868quluz22r244slhkk3e9/58hvh8ugq0gg6ma7/aHR0cHM6Ly9sZWFybi5qdXN0aW53ZWxzaC5tZS9jcmVhdG9yLW1iYS1tYXN0ZXJjbGFzcy8_Y291cG9uX2NvZGU9Q01CQTIwMjZGTEFTSFNBTEU= ) is my complete business playbook. Every framework and system I used to grow my following to 1.5M and my business to $12M in revenue at 90% margins. Learn how to finally monetize your expertise! Your Email Preferences: Your email address is b@email.gomodulr.com Change your account details ( https://preferences.convertkit-mail4.com/d0umk08qr7a0hov868quluz22r244slhkk3e9 )↗ ( https://b9bcc769.click.convertkit-mail4.com/d0umk08qr7a0hov868quluz22r244slhkk3e9/48hvh7umv9mmxlhq/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) Unsubscribe from all emails ( https://b9bcc769.unsubscribe.convertkit-mail4.com/d0umk08qr7a0hov868quluz22r244slhkk3e9 )↗ ( https://b9bcc769.click.convertkit-mail4.com/d0umk08qr7a0hov868quluz22r244slhkk3e9/48hvh7umv9mmxlhq/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) 30 Main Street PO Box 448, Accord, NY 12404-9998

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Rock bottom.

hello@justinwelsh.me2/14/2026

Kit

* * * *************** He was only 25. *************** Read on my website ( https://b9bcc769.click.convertkit-mail4.com/27uqlw34n0hoh8605m9a8ug338344hghmmvr9/e0hph0u7mdzvgnh7/aHR0cHM6Ly93d3cuanVzdGlud2Vsc2gubWUvbmV3c2xldHRlci8yNQ== ) / Read time: 4 minutes Last weekend, my wife, Jennifer, and I visited Williams Selyem winery, one of the best-regarded pinot noir producers in California. It was a perfect sunny afternoon for wine tasting, and we were struck by rolling hills covered in grapevines as we approached the estate through a big iron gate. This is a serious wine producer, and we were thrilled to have a reservation. As we hopped out of our Uber, a young guy greeted us, introducing himself as our host for the afternoon, Hess. He was friendly and relaxed with a laid-back California “surfer guy” kind of energy. We followed Hess into the building and made our way to a table reserved with our name on it, covered in maps and charts and wine glasses, of course. Everything seemed to track with the serious vibe we were expecting. But we couldn’t help but notice that the host at the next table was a much older man than our young host. And I secretly pondered the benefit of being educated by the older gentleman. He looked like he’d been working there for forty years, and I thought that maybe our guy was just an intern. But then Hess started talking. Assumptions vs reality ---------------------- He poured a Chardonnay and explained (rather scientifically) why it doesn’t taste like the oaky, buttery Chardonnays I usually hate. Something about cooler temperatures and slower ripening that lets the acidity develop. I’m probably not relaying that information exactly right, but I have a long history of not appreciating Chardonnay. But this one was absolutely delicious. As Hess moved through the tasting, I was locked into his ability to tell great stories. Jennifer asked a ton of questions, and Hess met her curiosities with ease, familiarity, and genuine passion. Sure, he knows his Williams Selyem history. But he also shared stories about working long days in vineyards, pruning and picking grapes. And he has a pulse on dozens of other wine makers in the area, who trained under who, and what other wines we should try based on things we said. He told us about restaurants we should visit and that he wants to make his own wine someday. He just hasn’t found the time to get started yet. By the end of our tasting, we were totally impressed with Hess. He was a wealth of information, and not in a scripted kind of way. He knew so much and shared his knowledge so generously. We genuinely enjoyed talking with him and learning from him. I was curious about his age, so I finally just asked him. And he chuckled a little, like he's gotten this question before. “Twenty-five,” he told us. Jennifer and I looked at each other in disbelief. We offered self-deprecating jokes about how immature and lost we were at his age, and we encouraged Hess to start making his own wine. On the ride home, we talked about Hess, and I recalled my first impression of him when I’d wished the older guy was our host. I’d quietly written him off for no real reason. And that’s not the first time I’ve done that. A taxi from New York City ------------------------- A few years ago, I got an email from a guy named Eric Partaker. When it hit my personal inbox, I was surprised because I didn't recognize the name. He said he was coming to NYC to meet up with another creator friend of mine who’d recommended Eric reach out to me, too. Eric asked if I could grab lunch while he was in the city. I looked at his LinkedIn profile, and he had about 4,000 followers at the time. Outside of one or two mutual connections, I couldn’t see anything else we had in common. Plus, I live two and a half hours from the city. So this wasn't a convenient ask. And I assumed it wasn't worth the trip. So I declined, citing the logistical challenges and wishing him well. But he quickly responded, saying he'd take a taxi up to the Hudson Valley to meet me. That kind of threw me. I mean, who takes a two-and-a-half-hour taxi to meet a stranger for lunch? I eventually said yes, mostly out of curiosity about someone who was that persistent. We met for lunch at a place near my house, and within minutes, I knew I'd been an idiot. Eric walked me through his experience co-founding Chilango, a major Mexican food chain in the UK that he started back in 2007 with a colleague from Skype. Eric had been building real businesses for nearly two decades. When I met him, he just happened to be in the early stages of building his online audience. We had a fabulous lunch, exchanged business stories, and learned about each other’s passion for traveling. That lunch date was three years ago. Today, Eric has over a million LinkedIn followers, runs a multi-million dollar business, and has become a good friend of mine. Jennifer and I hung out with him and his wife the last time we were in Lisbon, romping around the city, cocktailing, and eating Piri-Piri chicken. It turns out Eric and I have a whole lot in common. And I almost didn’t meet him because of his follower count. I cringe at the thought of how foolish that sounds. What I keep thinking about -------------------------- Two different people, in two completely different situations, with the same mistake on my end. The scary thing is how automatic it was both times. I didn't sit down and consciously decide "this person isn't worth my time." The assumption just ran quietly on autopilot in the background, making decisions about people before they'd had a chance to show me who they were. With Hess, it was just his age compared to his colleague at the next table. And with Eric, it was a follower count and an unfamiliar name in my inbox. Both times, I got lucky. Hess won me over before I could tune out. And Eric’s persistence made it impossible not to meet up with him. But now I wonder how many times I haven’t been that lucky. How many conversations have I half-listened to because I'd already decided what the other party probably had to offer? Or how many should-have-been conversations did I miss entirely? The thing is, you never know what you missed when you miss it. You just move along, none the wiser. I wonder how many friends, business partners, and influential additions to my network I've whiffed on by making assumptions. Catch yourself -------------- The funny thing about self-awareness is we usually don’t know when we’re lacking it. And worse, our brains are wired to make quick decisions and to filter out information that doesn’t feel important. But what if this evolution is actually filtering out opportunities for new people and new things that we’d love if we gave them a chance? What if our filters are working against us? So this week, I have a challenge for you. Try to catch yourself in the act of forming micro-assumptions based on unverified information. And then ask yourself, “What if I’m not right about this?” Give something a try that you’d usually filter out, just to see what happens. If you have an interesting experience (and you’re open to sharing), I’d love to hear about it. I can't write back to everyone, but Jennifer and I read every response, and we love hearing from you. That's all for this week. See you next Saturday. Justin Welsh Find me on X ( https://b9bcc769.click.convertkit-mail4.com/27uqlw34n0hoh8605m9a8ug338344hghmmvr9/owhkhwuwx0e9vrtq/aHR0cHM6Ly90d2l0dGVyLmNvbS90aGVqdXN0aW53ZWxzaC8= ), LinkedIn ( https://b9bcc769.click.convertkit-mail4.com/27uqlw34n0hoh8605m9a8ug338344hghmmvr9/z2hgh7ue5mz6vebz/aHR0cHM6Ly93d3cubGlua2VkaW4uY29tL2luL2p1c3RpbndlbHNoLw== ), Instagram, ( https://b9bcc769.click.convertkit-mail4.com/27uqlw34n0hoh8605m9a8ug338344hghmmvr9/p8hehqu4rpe60gtr/aHR0cHM6Ly93d3cuaW5zdGFncmFtLmNvbS90aGVqdXN0aW53ZWxzaC8= ) or Book a 1:1 Call ( https://b9bcc769.click.convertkit-mail4.com/27uqlw34n0hoh8605m9a8ug338344hghmmvr9/x0hph3uek4m263ug/aHR0cHM6Ly9pbnRyby5jby9KdXN0aW5XZWxzaA== ) Join 10K+ entrepreneurs in my business Masterclass: --------------------------------------------------- The Creator MBA Masterclass ( https://b9bcc769.click.convertkit-mail4.com/27uqlw34n0hoh8605m9a8ug338344hghmmvr9/6qhehoulx34rg0h9/aHR0cHM6Ly9sZWFybi5qdXN0aW53ZWxzaC5tZS9jcmVhdG9yLW1iYS1tYXN0ZXJjbGFzcy8_Y291cG9uX2NvZGU9Q01CQTIwMjZGTEFTSFNBTEU= ) is my complete business playbook. Every framework and system I used to grow my following to 1.5M and my business to $12M in revenue at 90% margins. Learn how to finally monetize your expertise! Your Email Preferences: Your email address is b@email.gomodulr.com Change your account details ( https://preferences.convertkit-mail4.com/27uqlw34n0hoh8605m9a8ug338344hghmmvr9 )↗ ( https://b9bcc769.click.convertkit-mail4.com/27uqlw34n0hoh8605m9a8ug338344hghmmvr9/kkhmh2unzopwqzuk/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) Unsubscribe from all emails ( https://b9bcc769.unsubscribe.convertkit-mail4.com/27uqlw34n0hoh8605m9a8ug338344hghmmvr9 )↗ ( https://b9bcc769.click.convertkit-mail4.com/27uqlw34n0hoh8605m9a8ug338344hghmmvr9/kkhmh2unzopwqzuk/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) 30 Main Street PO Box 448, Accord, NY 12404-9998

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He was only 25.

hello@justinwelsh.me2/7/2026

Kit

* * * **************** One person away. **************** Read on my website ( https://b9bcc769.click.kit-mail6.com/75u4zlq5x6s8h6dg858s9uweg7o66bnh00gpq/3ohphdu3xm8663hp/aHR0cHM6Ly93d3cuanVzdGlud2Vsc2gubWUvbmV3c2xldHRlci9vbmUtcGVyc29u ) / Read time: 3.5 minutes Last week, Jennifer and I ate at a tiny sushi restaurant here in Sonoma County. It’s tucked behind another restaurant, and you have to know where the hidden door is to get in. Basically, a sushi speakeasy that seats eight guests at a time. They serve a traditional "omakase" menu, where the chef chooses the best products of the day and serves them one piece at a time. The food blew us away, to say the least. So naturally, we became curious about the chef, and we struck up a conversation with him. He told us he’s from Venezuela, and we talked about how he became a chef. His story about growing up in Venezuela wasn’t easy. But around age 12, he ate a California roll for the first time. "My friends thought it was gross," he told me. "But to me it was the most interesting thing I'd ever tasted. I'd never had anything like it." Something clicked for him, and he fell in love with sushi. He eventually moved to Los Angeles with a dream of working at a sushi restaurant in the United States. He walked into 15 different places looking for work, dropping his resume and asking if they needed some help. And fourteen of them never got back to him. But he connected with one chef, and that chef saw something worth betting on. So he offered him a chance to start at the bottom. Over the next few years, he learned everything he could and worked his way up to apprenticing under that chef for years. Fast forward to today, and this guy who grew up in Venezuela runs his own kitchen, serving some of the best sushi we’ve ever had. As Jennifer and I walked home, we wondered about how different his life could have been if he hadn't eaten that California roll. Or what he'd be doing now if he hadn't met his mentor at that restaurant in Los Angeles. That one person who made a world of difference. The distance between here and there ----------------------------------- The sushi chef didn't find his mentor by having the perfect resume or knowing the right people. He walked into 15 restaurants in a city he barely knew (probably nervous as could be), and he was ignored. But he kept showing up, and eventually someone saw something in him worth betting on. And that's how these things tend to work, if you ask me. You can't manufacture the moment someone decides to take a chance on you. You can't engineer it or “deserve” your way into it. All you can do is keep putting yourself in the rooms and the situations where it might happen. I'm not a "woo-woo" kind of guy, and I don't believe in fate. But I do believe the distance between the person you are now and the person you want to be might just be one conversation away, with one person who sees something in you before you even see it in yourself. I believe this because it happened to me too. My person --------- Until age 28, I was, by all accounts, a very poor employee. I spent my early career bouncing around small towns, trying to find footing at jobs I pretty much hated. In seven years, I lived in four tiny Midwest towns. From town to town I went, underperforming and getting fired. And if you'd asked anyone who knew me during those years whether I'd eventually become a Chief Revenue Officer (or entrepreneur), they would have laughed in your face. Then I met Cyrus Massoumi, the founder of Zocdoc. In late November of 2009, I took a bus from Allentown, Pennsylvania, to New York City for an interview with him for a sales job. Cyrus hired me as a door-to-door salesman and tossed me into a Staten Island territory. I’d have to take the ferry back and forth every day, and I wouldn’t have a car on the island. Walking was what I’d have to do. And he told me to go make four sales a week. Despite the obvious challenges, I loved it. And for the first time in my life, I was actually good at something. Four months later, I was promoted with a $30,000 raise I hadn’t asked for. And not long after that, it was time to launch a new team in San Francisco. Cyrus picked me to lead the charge. Next was Boston, and he picked me again. When it was time to assign a manager to the entire West Coast, I got that job too. Cyrus picked me for so many things. And with his confidence, I kept rising to meet the challenges. He was the guy who gave me a shot. And I pinpoint that as the most critical moment that shaped my career, and ultimately the business and life I’ve been able to build with Jennifer. Cyrus was my LA sushi chef. The bottom line --------------- Somewhere in Sonoma County, there's a chef running an amazing eight-seat sushi bar because someone in Los Angeles saw something in a kid from Venezuela who probably had no business getting that shot. And somewhere in New York, there's a guy who went from getting fired all over the Midwest to building his own business, because somebody took a chance on him. You can't force moments like these. And you can't optimize your way into them. But you can put yourself in rooms where they're possible. You can say yes to opportunities you're not quite ready for. And you can strike up conversations with people who are doing things you want to do. Because someone might see something in you before you see it in yourself. You probably won't recognize these moments when they're happening. That dishwasher job at a sushi restaurant in LA probably didn’t feel pivotal. And applying to a small startup in NYC was just another job interview for me. You can’t know what ordinary experience might introduce you to the person who redirects your whole trajectory. But you can keep showing as the best version of yourself in ordinary situations. And more importantly, you can challenge yourself to explore opportunities beyond your current routine. So here's my question for you this week: How can you push beyond your comfort zone? What’s something you could try that might unlock more opportunities for you to get from Point A (today) to Point B (where you want to be)? Reply and tell me. While I can't reply to everyone, Jennifer and I read every response, and we love hearing from you. That's all for this week. See you next Saturday. Justin Welsh Find me on X ( https://b9bcc769.click.kit-mail6.com/75u4zlq5x6s8h6dg858s9uweg7o66bnh00gpq/wnh2h6uqm7d998tl/aHR0cHM6Ly90d2l0dGVyLmNvbS90aGVqdXN0aW53ZWxzaC8= ), LinkedIn ( https://b9bcc769.click.kit-mail6.com/75u4zlq5x6s8h6dg858s9uweg7o66bnh00gpq/reh8h9umkdp99kt6/aHR0cHM6Ly93d3cubGlua2VkaW4uY29tL2luL2p1c3RpbndlbHNoLw== ), Instagram, ( https://b9bcc769.click.kit-mail6.com/75u4zlq5x6s8h6dg858s9uweg7o66bnh00gpq/8ghqh3uowd8eedhl/aHR0cHM6Ly93d3cuaW5zdGFncmFtLmNvbS90aGVqdXN0aW53ZWxzaC8= ) or Book a 1:1 Call ( https://b9bcc769.click.kit-mail6.com/75u4zlq5x6s8h6dg858s9uweg7o66bnh00gpq/l2heh6ulq2p559ig/aHR0cHM6Ly9pbnRyby5jby9KdXN0aW5XZWxzaA== ) Join 10K+ entrepreneurs in my business Masterclass: --------------------------------------------------- The Creator MBA Masterclass ( https://b9bcc769.click.kit-mail6.com/75u4zlq5x6s8h6dg858s9uweg7o66bnh00gpq/dphehmued6xzzlbl/aHR0cHM6Ly9sZWFybi5qdXN0aW53ZWxzaC5tZS9jcmVhdG9yLW1iYS1tYXN0ZXJjbGFzcy8_Y291cG9uX2NvZGU9Q01CQTIwMjZGTEFTSFNBTEU= ) is my complete business playbook. Every framework and system I used to grow my following to 1.5M and my business to $12M in revenue at 90% margins. Learn how to finally monetize your expertise! Your Email Preferences: Your email address is b@email.gomodulr.com Change your account details ( https://preferences.kit-mail6.com/75u4zlq5x6s8h6dg858s9uweg7o66bnh00gpq )↗ ( https://b9bcc769.click.kit-mail6.com/75u4zlq5x6s8h6dg858s9uweg7o66bnh00gpq/e0hph0u7mvz99rf7/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) Unsubscribe from all emails ( https://b9bcc769.unsubscribe.kit-mail6.com/75u4zlq5x6s8h6dg858s9uweg7o66bnh00gpq )↗ ( https://b9bcc769.click.kit-mail6.com/75u4zlq5x6s8h6dg858s9uweg7o66bnh00gpq/e0hph0u7mvz99rf7/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) 30 Main Street PO Box 448, Accord, NY 12404-9998

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One person away.

hello@justinwelsh.me1/31/2026

Kit

* * * ************************ Being a purple squirrel. ************************ Read on my website ( https://b9bcc769.click.kit-mail6.com/qdu2gzend7f7h4e5r5ligu82pvrkki4hpp9wn/08hwhgu2ngd097sp/aHR0cHM6Ly93d3cuanVzdGlud2Vsc2gubWUvbmV3c2xldHRlci9wdXJwbGUtc3F1aXJyZWw= ) / Read time: 4 minutes Eleven years ago, I was sitting in the Financial District WeWork in Manhattan, watching one of my sales guys tape together a paper pyramid. I was in my second month as VP of Sales at PatientPop, and I had just hired and trained our second salesperson, Sagar Patel ( https://b9bcc769.click.kit-mail6.com/qdu2gzend7f7h4e5r5ligu82pvrkki4hpp9wn/reh8h9umkw093ec6/aHR0cHM6Ly93d3cubGlua2VkaW4uY29tL2luL3NhZ2FyLXBhdGVsLTAxLw== ). Back when Sagar joined the team, we were a seed-funded startup with barely any resources. We didn't have a marketing team, there were no inbound leads, white papers or case studies, and certainly no marketing slicks. We had a half-functioning website, maybe seven example customers, and about $40K in annual revenue. That was basically it. Most salespeople in that situation would complain. Where are my leads? Where's marketing? I need better resources! I've heard some version of that from just about every salesperson I ever managed. But Sagar saw a different problem to solve. He needed to explain local SEO to physicians in a simple way. Marketing can be complicated, especially for doctors who just want to show up to work and see patients. They don't care about search algorithms and profile optimization. They care about getting more patients through the door. So Sagar grabbed some notebook paper and drew five sides of a pyramid. He labeled each one, describing his "5 sides of local SEO for healthcare providers," and then taped them all together. He made himself a little paper pyramid to use in his sales pitches. A purple squirrel ----------------- In recruiting, there's a weird term called a "purple squirrel." A purple squirrel is a candidate so rare and perfectly matched to what you need that finding one feels impossible. Someone who checks every single box, including boxes you didn't even know you cared about. Sagar was a purple squirrel for me at PatientPop. I needed someone who could sell, of course. But I also needed someone who could create their own pitch from scratch when we had nothing. Someone who could handle objections without a playbook and design their own marketing materials. And most importantly, I needed someone completely self-motivated, who’d figure stuff out instead of complaining about what they didn’t have. The paper pyramid was purple squirrel energy in action. I remember watching him use it on a call with a practice manager. He held up his janky little pyramid, turned it around to explain each side, and walked through the strategy like he was presenting to a billion-dollar CEO. The practice manager nodded along, engaged throughout the call. And that day, they signed a deal worth $14,300 in annual contract revenue (nearly triple the size of our average deal at the time). Sagar used his paper pyramid for a full year and probably closed over 200 deals with it. He could make as many as he needed and say, "Keep this on your desk," if he couldn't get the deal done. The doctor would see it daily and call back to say, "Let's move forward." Eventually, the pyramid became the foundation for our first real marketing slick, the one that the actual designers made once we could afford to hire them. By the time I left PatientPop four and a half years later, the company had grown to over $70 million in revenue. And I still think about that paper pyramid taped together with notebook paper. Why the paper pyramid worked ---------------------------- Most people in Sagar's situation would have waited for the marketing team to produce a professional PDF or for a designer to create a "proper” infographic to use in front of customers. They would have complained about not having the right tools to hit their quota instead of making their own. But from day one, Sagar knew today’s scrappy version beats the polished version you're waiting for. That pyramid worked partly because it existed. Because it was a tangible object that doctors could hold in their hands and examine. They didn't need a beautiful marketing piece. They needed someone to make a complicated topic like SEO easy to understand. And Sagar did that with a pencil, notebook paper, and tape. People wait months for perfect conditions all the time. They think they have to launch with a gorgeous website, the best visuals, and the right pitch deck. So they procrastinate for months or even years, while some purple squirrel is out there with a paper pyramid, closing deals. What I did with my first product -------------------------------- I think about Sagar's pyramid all the time, especially when I look back at my first product launch. The idea for that product came in the spring of 2020. I was living in Los Angeles, and I had a LinkedIn following of about 21,000 people, which was a huge number back in the day. I had grown my following by writing about healthcare consulting, sales, marketing, and building software companies. But every week, when I opened up my DMs, most of the questions were some version of: How are you growing so fast on LinkedIn? I would have ignored those questions entirely if my friend Kevin Dorsey hadn’t seen the writing on the wall (that I was definitely missing). “Why don’t you teach people how to grow on LinkedIn?” Kevin asked. I'd been reading Russell Brunson's books on online marketing, and I started thinking there might be a digital product in these LinkedIn questions. So I decided to find out. I sat down in front of my webcam and recorded myself walking through PowerPoint slides I'd designed myself. No professional setup or studio with fancy lighting. And no script. I just talked through my slides like I was explaining them to a friend. It took about 90 hours to put my first product together, and I didn’t do any editing. I priced it at $50 and put it up for sale. I launched with a single LinkedIn post on April 16th. And that day, I made $300. I can still remember the very first time my phone pinged with a little cash-register sound. I glanced down at it and realized that a stranger on the internet had just paid me $50 for something I created. I was utterly shocked. That first sale was a huge unlock for me. I remember thinking, "I can actually do this." That product was called The LinkedIn Playbook, and I sold $10,482 in my first month. Over the next 18 months, that ugly little webcam course did $75,000 more in sales before I finally retired it. And when I updated and rereleased it as The LinkedIn OS, it generated over $4.5 million in sales. None of that would have happened if I'd waited for professional lighting or a real studio or a proper script. I learned what to build by building the ugliest possible version first. The bottom line --------------- Sagar's paper pyramid closed over 200 deals and became the marketing foundation for a company that grew to $70 million. It had less to do with design and more to do with Sagar needing to explain local SEO in a way a physician would understand. So he got to work with the only tools he had. His hands, some paper, a pencil, and tape. When you're building something from scratch, you don't have the luxury of waiting for perfect conditions. And you don’t need perfect conditions anyway. You don't get a marketing team, a design budget, or someone handing you a playbook on day one of building your own business. You get the equivalent of notebook paper and tape. And the question is whether you'll make something with it or sit around wishing you had more. So here's my question for this week: What's the paper pyramid you can make now? What's the scrappy, imperfect little thing you've been avoiding because you're waiting for the "right" way to do it? Maybe it's time to tape something together and see what happens. Write back and tell me about your paper pyramid. I can't reply to everyone, but Jennifer and I read every response, and we love hearing from you. That's all for this week. See you next Saturday. Justin Welsh Find me on X ( https://b9bcc769.click.kit-mail6.com/qdu2gzend7f7h4e5r5ligu82pvrkki4hpp9wn/vqh3hmuomep2vpiw/aHR0cHM6Ly90d2l0dGVyLmNvbS90aGVqdXN0aW53ZWxzaC8= ), LinkedIn ( https://b9bcc769.click.kit-mail6.com/qdu2gzend7f7h4e5r5ligu82pvrkki4hpp9wn/l2heh6ulq635nlfg/aHR0cHM6Ly93d3cubGlua2VkaW4uY29tL2luL2p1c3RpbndlbHNoLw== ), Instagram, ( https://b9bcc769.click.kit-mail6.com/qdu2gzend7f7h4e5r5ligu82pvrkki4hpp9wn/m2h7h6u32m8kqmtl/aHR0cHM6Ly93d3cuaW5zdGFncmFtLmNvbS90aGVqdXN0aW53ZWxzaC8= ) or Book a 1:1 Call ( https://b9bcc769.click.kit-mail6.com/qdu2gzend7f7h4e5r5ligu82pvrkki4hpp9wn/dphehmued80zo5fl/aHR0cHM6Ly9pbnRyby5jby9KdXN0aW5XZWxzaA== ) Join 10K+ entrepreneurs in my business Masterclass: --------------------------------------------------- The Creator MBA Masterclass ( https://b9bcc769.click.kit-mail6.com/qdu2gzend7f7h4e5r5ligu82pvrkki4hpp9wn/e0hph0u7mq09l5t7/aHR0cHM6Ly9sZWFybi5qdXN0aW53ZWxzaC5tZS9jcmVhdG9yLW1iYS1tYXN0ZXJjbGFzcy8_Y291cG9uX2NvZGU9Q01CQTIwMjZGTEFTSFNBTEU= ) is my complete business playbook. 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Being a purple squirrel.

hello@justinwelsh.me1/24/2026

Kit

* * * **************** Small by design. **************** Read on my website ( https://click.kit-mail6.com/o8unwm0plofqh6xov2rcquqzd58rraoh446nw/g3hnhwumgn0l84s3/aHR0cHM6Ly93d3cuanVzdGlud2Vsc2gubWUvbmV3c2xldHRlci9zbWFsbC1ieS1kZXNpZ24= ) / Read time: 4 minutes The Saturday Solopreneur is brought to you by: Free: Grow Your Business By Writing (4 simple steps) ---------------------------------------------------- Do you want to become a writer? Kieran Drew attracted 250k readers and made $1.5m in 4 steps. Get his exact roadmap here: Read the guide ( https://click.kit-mail6.com/o8unwm0plofqh6xov2rcquqzd58rraoh446nw/reh8h9umk7o3g2f6/aHR0cHM6Ly9raWVyYW5kcmV3LmtpdC5jb20vZGRiMTc1YjQxZD91dG1fY2FtcGFpZ249ZGVmYXVsdC1jYW1wYWlnbiZ1dG1fY29udGVudD1tb2F0JnV0bV9tZWRpdW09YWQmdXRtX3NvdXJjZT1qdXN0aW53ZWxzaA== ) Jennifer and I are spending this winter in California, and we're enjoying our new little town, Healdsburg. This is prime wine country, a landscape that suits us well, and we're not doing Dry January. So last Sunday, we walked into a tiny Champagne bar late in the afternoon. It's appropriately named, The Healdsburg Bubble Bar, and it has about 12 seats. The place is a hidden gem with cozy decor and Parisian vibes. You won't find beer or cocktails on the menu. And they don't cook anything. Sparkling wine and champagne are the only things they serve, and that's what this place is all about. As we sat down, a friendly woman emerged from behind the bar and greeted us with such enthusiasm that we suspected she must be the owner. We watched her move around the room, pouring champagne and chatting with customers about wine, dogs, traveling, and all kinds of other things. And it wasn't long before we were chatting with her, too. Her name is Sarah, and we confirmed that she is, in fact, the owner. Sarah's energy perfectly matches her menu. Bubbly. She's the kind of person who makes you want to stay longer than you planned. You can tell she loves this. Sarah told us she spent 25 years working in the wine industry. She's an award-winning winemaker who ended up overseeing more responsibilities as her career grew. Somewhere along the way, she got tired of staring at spreadsheets. And when Covid came along, she found herself gravitating toward sparkling wines, inspired by Pops, a champagne bar she loves in Chicago. She started wondering why her wine-loving town, the one she'd grown up in, didn't have a bar dedicated entirely to sparkling wine. So, at age 57, she opened one herself. Sarah had the resume to do something much bigger. Decades of experience, deep industry knowledge, and serious connections in wine country. She could have opened a winery or launched a full-service wine bar or restaurant with investors and employees and all the complexity that comes with that kind of operation. But she opened a bubbles-only bar with limited seating, no hot food, and she doesn't take reservations. She told us she has no employees, and she's running this small operation all by herself. I asked her if she ever thought about going bigger, and she laughed. "I spent 25 years going bigger. I know exactly what that costs." What bigger almost cost me -------------------------- I know what it costs, too. Or at least, I almost found out. When I left my corporate job, I was pulled toward scale. I'd spent years as a Chief Revenue Officer, and I believed my next thing should at least match that level. Going smaller felt like moving backward, so I looked for opportunities to "go big, or go home." Eventually, I went pretty far down the rabbit hole with another entrepreneur, and our idea was to go all-in on a SaaS idea. Our business plan was legitimately good, and we'd both be playing to our strengths. I had the marketing and sales chops, and he brought a strong operational background to the table. We'd spent months on that business idea when I called him to back out. I thought about the team we planned to build, the office space we'd need, the infrastructure, and the stress that would surely come with building the business we imagined. And it just hit me all at once. I was setting myself up for days that would look and feel a lot like the career I'd just left behind. And that vision crystallized my decision to scrap the idea. I'm still not sure I made the right call. For all I know, that business could be doing eight figures in ARR by now. I'll never know where that path might have taken me. I can only speak for the path I took instead. My office is a bedroom in our house, but I spend most days writing from my kitchen island. No employees. No team meetings. No business partner to negotiate with, and no investors to answer to. The only person who influences whether or not I can book a vacation is our petsitter. Some days this feels like total freedom, and I just pinch myself. And other days, I wonder if I just got scared. The question I keep asking myself --------------------------------- There's a version of going small that's a conscious choice. You know what kind of business you want to build, you know what it costs, and you create something that fits. And there's a version where staying small is just letting fear win. I think about "more" and "scale" pretty often. I do wonder what it would be like to be featured in the big magazines and to be in rooms where teams are raising rounds of funding. Every time I see a friend raising a Series A or hitting some massive revenue milestone, there's a little voice that says, "You could have done that." But then I imagine what my life would probably look like today if I'd built that almost-business. I'd be in meetings all day and managing people again. I'd be checking Slack after dinner and feeling guilty about taking time off on a weekday to take my dog to the vet. I'd be putting out technology fires from vacations like I did back in my startup days. I'd have traded my relaxed lifestyle, my flexible hours, and my ability to spend the winter in California for equity in something that might not even work. The money might have been better. The press and headlines surely would have. But I'm quite certain my life wouldn't be. What Sarah actually figured out ------------------------------- When I got around to asking Sarah about her days off, she told us Sunday nights are her Friday nights. (It was a Sunday.) She said she spends her days off cooking, visiting the coast, and painting. An award-winning winemaker with 25 years of experience spends her Mondays and Tuesdays painting. That's not something you get to do if you run a 50-seat restaurant with a staff, a reservations system, and a chef. Or when you're managing inventory, HR issues, and investor expectations. Hobbies like painting and cooking (and having the time to do them) are usually the first things you sacrifice when you build the bigger version. Sarah didn't go small because she couldn't go big. She went small because she'd already seen what big costs. She spent 25 years watching herself and other people pay that price. And when it was her turn to build something, she made a different choice. Not because she was scared. Because she's confident about what she wants. The bottom line --------------- We had a lot of fun watching Sarah work the room, operating her business. She had a big smile on her face as she poured glasses of bubbly, encouraged us to do a blind tasting, and waved more people in from the sidewalk. She decided to use her expertise and experience to build the smallest possible version of something she loves. Most people will spend their whole careers chasing scale they never needed. They'll drive themselves into the ground trying to find more clients, more revenue, more of everything. And somewhere in the middle of all that chasing, they forget why they started doing it all in the first place. Scale is the default. Enough is a decision. I'm still figuring out what "enough" looks like for me. I feel like I'm getting closer all the time. And sitting in that tiny Champagne bar, watching Sarah do exactly what she wants to be doing, I got a glimpse of what it might feel like to stop wondering. So here's my question: What would your version of the Bubble Bar look like? If you stripped away everything you think you're supposed to build and just focused on the part you actually love, what would be left? Reply and tell me. While we can't reply to everyone, Jennifer and I read every single response. That's all for this week. See you next Saturday. Justin Welsh Find me on X ( https://click.kit-mail6.com/o8unwm0plofqh6xov2rcquqzd58rraoh446nw/l2heh6ulq4dn8zig/aHR0cHM6Ly90d2l0dGVyLmNvbS90aGVqdXN0aW53ZWxzaC8= ), LinkedIn ( https://click.kit-mail6.com/o8unwm0plofqh6xov2rcquqzd58rraoh446nw/e0hph0u7medl80t7/aHR0cHM6Ly93d3cubGlua2VkaW4uY29tL2luL2p1c3RpbndlbHNoLw== ), Instagram, ( https://click.kit-mail6.com/o8unwm0plofqh6xov2rcquqzd58rraoh446nw/p8hehqu4rdp2n8cr/aHR0cHM6Ly93d3cuaW5zdGFncmFtLmNvbS90aGVqdXN0aW53ZWxzaC8= ) or Book a 1:1 Call ( https://click.kit-mail6.com/o8unwm0plofqh6xov2rcquqzd58rraoh446nw/25h2h9u3lgq8kzc8/aHR0cHM6Ly9pbnRyby5jby9KdXN0aW5XZWxzaA== ) Join 10K+ entrepreneurs in my business Masterclass: --------------------------------------------------- The Creator MBA Masterclass ( https://click.kit-mail6.com/o8unwm0plofqh6xov2rcquqzd58rraoh446nw/9qhzhdud4xe6o5bz/aHR0cHM6Ly9sZWFybi5qdXN0aW53ZWxzaC5tZS9jcmVhdG9yLW1iYS1tYXN0ZXJjbGFzcy8_Y291cG9uX2NvZGU9Q01CQTIwMjZGTEFTSFNBTEU= ) is my complete business playbook. Every framework and system I used to grow my following to 1.5M and my business to $12M in revenue at 90% margins. Learn how to finally monetize your expertise! Your Email Preferences: Your email address is b@email.gomodulr.com Change your account details ( https://preferences.kit-mail6.com/o8unwm0plofqh6xov2rcquqzd58rraoh446nw )↗ ( https://click.kit-mail6.com/o8unwm0plofqh6xov2rcquqzd58rraoh446nw/3ohphdu3xrk2ekhp/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) Unsubscribe from all emails ( https://unsubscribe.kit-mail6.com/o8unwm0plofqh6xov2rcquqzd58rraoh446nw )↗ ( https://click.kit-mail6.com/o8unwm0plofqh6xov2rcquqzd58rraoh446nw/3ohphdu3xrk2ekhp/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) 30 Main Street PO Box 448, Accord, NY 12404-9998

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Small by design.

hello@justinwelsh.me1/17/2026

Kit

* * * ********************* Nobody's even trying. ********************* Read on my website ( https://click.kit-mail6.com/n4ur3ewzl6fvhx2og3eh0u68qvkggalhoo398/08hwhgu2qpdnmmbp/aHR0cHM6Ly93d3cuanVzdGlud2Vsc2gubWUvbmV3c2xldHRlci90cnlpbmc= ) / Read time: 4 minutes The Saturday Solopreneur is brought to you by: The 36 Best Marketing Ideas for 2026 ------------------------------------ From MarketingIdeas.com ( https://click.kit-mail6.com/n4ur3ewzl6fvhx2og3eh0u68qvkggalhoo398/reh8h9umno0kq5f6/aHR0cDovL21hcmtldGluZ2lkZWFzLmNvbS8= ) - the newsletter 60,000+ marketers subscribe to. Real tactics, real numbers, zero fluff. Read All 36 Free → ( https://click.kit-mail6.com/n4ur3ewzl6fvhx2og3eh0u68qvkggalhoo398/vqh3hmuo8qpmnofw/aHR0cHM6Ly93d3cubWFya2V0aW5naWRlYXMuY29tL3AvMjAyNg== ) Free Workshop: Build a $10k/Month Newsletter in 2026 ---------------------------------------------------- Join Tuesday's private workshop for TSS readers. Start a newsletter, scale to 1,000 readers, and launch ads, digital products, or services. Save Your Free Seat ( https://click.kit-mail6.com/n4ur3ewzl6fvhx2og3eh0u68qvkggalhoo398/vqh3hmuo8qpmnofw/aHR0cHM6Ly9jbGFzcy50aGVmZWVkbWVkaWEuY29tL3NhdHVyZGF5LXNvbG9wcmVuZXVyLXdvcmtzaG9wLw== ) Everyone keeps telling me how hard it is to win right now. I hear it constantly. How saturated the market is, how many competitors are out there, and how AI is making everything even more commoditized than it was before. There are too many people doing the same thing, and it's impossible to stand out and win anymore. Every conversation I have with an entrepreneur eventually lands on some version of "it's just so much harder than it used to be." And I get it. It definitely feels that way sometimes. But then I look around at my actual experiences as a customer, and I start to wonder if we're all talking about the same world. Because I've never had more bad customer experiences in my life than I'm having right now. There's a hotel near my house in the Hudson Valley called The Hasbrouck House. It's a beautiful old stone building built in 1757 that (at one point) had great food, a nice bar, and packed crowds. When Jennifer and I moved to the area a little over three years ago, it was the kind of place we'd take friends when they visited. Especially on Wednesday nights when they ran a burger special that packed the place from wall to wall. That was a regular occurrence for us in 2023. Fast forward to the first week of 2026, and they announced they were closing for good. Both the hotel and restaurant are done. I texted a few friends to see if they'd heard. Nobody was surprised. "We've been saying that for years," one of them replied. "It's been empty for the last year." "Kind of shocking they couldn't make it work, huh?" But it wasn't shocking. Not to anyone who'd been there recently, at least. The night it clicked -------------------- Back in late 2024, Jennifer and I walked in, and the bar looked open, but nobody was behind it. There wasn't a bartender or a host to talk to. Just empty stools and some loud indie music playing in the background. We sat down in our usual spot and waited for someone to come out. Meanwhile, another couple came in and stood at the host stand looking around, clearly expecting someone to greet them. For about five or six minutes, nobody came. Long enough that I started feeling uncomfortable for them as they just stood there, looking around, wondering if anyone was going to help. Eventually, a frazzled bartender appeared from the back. He yelled loudly for the hostess to come, and she appeared, acting surprised that people had come into the restaurant. Jennifer and I shook off the experience and ordered a glass of wine and a beer. The bartender told me that all three draft lines were down, so I had to opt for a can instead. When Jennifer's wine came out, it was the wrong one, and it was warm. She mentioned it to the bartender, and he said he'd grab a cold bottle from the wine fridge. Ten minutes later, with almost half of my beer already gone, he came back and told her they were actually out of that wine completely. No offer to grab something similar. No solution. He just stood there. As we left, we looked at each other in disbelief. What the hell had happened to this place? After hearing similar rumblings from friends, we agreed to take a break from going there. Six months later, we forgot and decided to give them another chance. We brought our dog Munchie, who'd been to the Hasbrouck House with us plenty of times before. He was always welcome in the bar. This time, the bar and restaurant were both empty, and we appeared to be the first customers of the night. As we walked in, a new host informed us that dogs weren't allowed. If we wanted to stay, we'd have to sit in the reading room. We wondered out loud if this was a new rule. Iron fist. No, this has always been the rule. There wasn't a single customer in the entire establishment. And they were turning away their first customers of the evening, over a rule that never existed, for a seven-pound dog who'd been coming for years. We didn't have the energy to argue. We just left. The pattern ----------- I've been noticing this kind of experience everywhere lately. A few months ago, when we were planning our winter sabbatical in California, I reached out to a few rental places to ask about staying. 90% of them never emailed me back. I finally heard from one three weeks later, who apologized in between telling me how hard it had become to make money as a host. And it's not just vacation rentals. Or restaurants. Contractors disappear mid-project, basic questions require three follow-ups, and proposals show up late or not at all. I'm not talking about rare disasters. I'm talking about the normal experience of trying to spend money with someone in 2026. The bar hasn't just dropped. It's fallen through the floor. And this is happening at the exact same time that everyone's panicking about how competitive the market is. How you need to find your niche, build your brand, and differentiate yourself. But stand out from what, exactly? From people who don't respond? From businesses that make it hard to buy from them? I'm not sure I'd call that a brutal competitive landscape. It feels more like folks beating themselves. What this actually means ------------------------ I think a lot of people don't realize just how important the unsexy stuff in business actually is. The communication, the expectation setting, the customer service, and the admin work. They believe the product or service quality speaks for itself, so they skimp on everything else. The Hasbrouck House had everything going for it. A historic building, killer location, great food, and reasonable prices. But none of it mattered because they couldn't manage to greet people at the door and bring the right drink. Over time, those small miscues compounded across their entire customer base. And people stopped showing up. For online businesses, the host stand could be your landing page. Or your checkout process. Or the email someone sends asking a question before they buy. Every one of those moments is a chance to make people feel taken care of, or a chance to lose them before they ever give you money. The good news? This stuff isn't complicated. It's just overlooked. Make it easy to pay. Answer the common questions before people have to ask. Deliver quickly after someone buys. Set expectations so people know what's coming and when. Respond to inquiries like you actually want the business. None of this is revolutionary. But right now, it's rare. Which means if you're someone who does these things, who responds within a reasonable timeframe, who makes it easy to do business with you, you're not just meeting the minimum. You're in rare company. The bottom line --------------- The Hasbrouck House had a 300-year-old building, a perfect location, great food, and they still couldn't make it work. But they didn't lose to a competitor with better food or a nicer space. They lost to themselves. They stopped paying attention to whether people felt taken care of when they walked through the door. The game isn't as hard as everyone thinks. The bar is on the floor. Showing up and making it easy for people to do business with you puts you ahead of almost everyone. So here's my question: where are you making it hard for people to give you money? Where is there friction in your process that frustrates the people who want to buy from you? Reply and tell me. While I can't reply to every person who writes in, I still read every response. That's all for this week. See you next Saturday. Justin Welsh Find me on X ( https://click.kit-mail6.com/n4ur3ewzl6fvhx2og3eh0u68qvkggalhoo398/m2h7h6u3wl82oebl/aHR0cHM6Ly90d2l0dGVyLmNvbS90aGVqdXN0aW53ZWxzaC8= ), LinkedIn ( https://click.kit-mail6.com/n4ur3ewzl6fvhx2og3eh0u68qvkggalhoo398/dphehmuer20dqril/aHR0cHM6Ly93d3cubGlua2VkaW4uY29tL2luL2p1c3RpbndlbHNoLw== ), Instagram, ( https://click.kit-mail6.com/n4ur3ewzl6fvhx2og3eh0u68qvkggalhoo398/e0hph0u75d0mkmb7/aHR0cHM6Ly93d3cuaW5zdGFncmFtLmNvbS90aGVqdXN0aW53ZWxzaC8= ) or Book a 1:1 Call ( https://click.kit-mail6.com/n4ur3ewzl6fvhx2og3eh0u68qvkggalhoo398/7qh7h2u93xod0qc9/aHR0cHM6Ly9pbnRyby5jby9KdXN0aW5XZWxzaA== ) Join 10K+ entrepreneurs in my business Masterclass: --------------------------------------------------- The Creator MBA Masterclass ( https://click.kit-mail6.com/n4ur3ewzl6fvhx2og3eh0u68qvkggalhoo398/z2hgh7ue0m35oxsz/aHR0cHM6Ly9sZWFybi5qdXN0aW53ZWxzaC5tZS9jcmVhdG9yLW1iYS1tYXN0ZXJjbGFzcy8_Y291cG9uX2NvZGU9Q01CQTIwMjZGTEFTSFNBTEU= ) is my complete business playbook. Every framework and system I used to grow my following to 1.5M and my business to $12M in revenue at 90% margins. Learn how to finally monetize your expertise! Your Email Preferences: Your email address is b@email.gomodulr.com Change your account details ( https://preferences.kit-mail6.com/n4ur3ewzl6fvhx2og3eh0u68qvkggalhoo398 )↗ ( https://click.kit-mail6.com/n4ur3ewzl6fvhx2og3eh0u68qvkggalhoo398/p8hehqu48pzr90tr/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) Unsubscribe from all emails ( https://unsubscribe.kit-mail6.com/n4ur3ewzl6fvhx2og3eh0u68qvkggalhoo398 )↗ ( https://click.kit-mail6.com/n4ur3ewzl6fvhx2og3eh0u68qvkggalhoo398/p8hehqu48pzr90tr/aHR0cHM6Ly93d3cudG9wdGFsLmNvbS9kZXNpZ25lcnMvaHRtbGFycm93cy9hcnJvd3Mvbm9ydGgtZWFzdC1hcnJvdy8= ) 30 Main Street PO Box 448, Accord, NY 12404-9998

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Nobody's even trying.

hello@justinwelsh.me1/10/2026

Kit

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The one question I've been dodging for years.

hello@justinwelsh.me1/3/2026

Kit

Hey ― Justin ( https://click.kit-mail6.com/mvupedxvl6u6uznvo2spfrk64lqqs3heeqgp/g3hnhwu374qe7wa3/aHR0cHM6Ly90d2l0dGVyLmNvbS90aGVqdXN0aW53ZWxzaA== ) here. Welcome to The Saturday Solopreneur Crew of 175,000+ solopreneurs, entrepreneurs, and creators. (Didn't mean to sign up? Click here ( https://unsubscribe.kit-mail6.com/mvupedxvl6u6uznvo2spfrk64lqqs3heeqgp )) I'm here to help you in two specific ways: * Leverage social media to build a valuable audience. * Build a lean, profitable business serving that audience. Most people are stuck on the first part. They're struggling to build an audience, and think they need to be on every platform at once. You don't. You need one platform and one proven system. As a gift for joining, I want to share my 2026 guide on how to build a following on the highest-ROI platform right now: LinkedIn. -->Read My 2026 LinkedIn Growth Guide ( https://click.kit-mail6.com/mvupedxvl6u6uznvo2spfrk64lqqs3heeqgp/x0hwm020c3ue3qndr8bg/aHR0cHM6Ly93d3cuanVzdGlud2Vsc2gubWUvYXJ0aWNsZS9saW5rZWRpbi1ndWlkZS0yMDI2 ) Read My 2026 LinkedIn Growth Guide ( https://www.justinwelsh.me/article/linkedin-guide-2026 )In this guide, you’ll learn: * Everything that's working on LinkedIn as we enter 2026. * How to use content to drive followers and engagement. * How to create content without spending a lot of time. I hope you enjoy it. Starting every Saturday, I'm going to send you one short email that helps you continue to grow your audience and monetize your expertise. To make sure you get it, please reply "Yes" to this email so I know this didn't land in spam. (and move this email from your "Promotions Tab" to your Inbox) Thanks again for joining. See you on Saturdays. Cheers, Justin

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It's Time to Upgrade Your Saturday 🔥

hello@justinwelsh.me12/16/2025

Kit

Explore all emails from Justin Welsh

Mediocrity at scale.

The machine is a mirror.

Having fun is the new moat.

Stop sharpening your axe.

Manufactured certainty.

Rich and broke.

The two-speed problem.

Unreasonable.

Your new rabbit hole.

Small enough to see.

There's no map for this.

Freedom. Sort of.

Sweat the small stuff.

Selective editing.

Synthetic purpose.

The machine or the life.

Pick a table.

Just tell me when you’ll be here.

Thief of joy.

Missing someone who doesn’t exist.

I'm a crazy person.

Bored to death.

Get out.

Rock bottom.

He was only 25.

One person away.

Being a purple squirrel.

Small by design.

Nobody's even trying.

The one question I've been dodging for years.

It's Time to Upgrade Your Saturday 🔥