How to Start Thinking in Systems
A few years ago, I was helping my friend Jeff rebuild an automation — getting his intake form to talk to his CRM and his project management tool. Halfway through the screen share, he stopped and said, "So you just think like this?" That's when it hit me: not everyone's brain defaults to systems. Mine does…but I wasn't born with it. I learned it. That's what this episode is about. A lot of solopreneurs tell me some people are just wired for this, and they're not, that it's a willpower fail. I don't…
The Lie That AI Is a Magic Shortcut
I was talking to an acquaintance recently who told me how he has AI agents write his articles for him. He sends a voice note of an idea, and every morning it picks the ideas, writes the drafts, sends them to him, he requests edits, and then it writes and publishes them. So I asked him: at what point do you feel uncomfortable putting your name on this? And he couldn't even see the issue. He just thought AI was some amazing magic bullet that produced articles for him. That's what I want to talk about…
You Don't Have to Fix Everything — Just Start With One Thing
Back in 2016, I ran…well, *completed…*a Disney half marathon. And the thing about Disney is they make it impossible not to find the starting line. Buses from the resort, signs, gates, pre-race emails. Everything points you to where to start. And if I didn’t know any of that, I wouldn’t just start running. I would start simple…like asking a cast member when the race is, and go from there. But for some reason, when it comes to our business, a lot of us tell ourselves: I have to fix everything…
"No One Can Do It Like Me" Is a Lie (And It's Costing You)
For most of my life, I believed that if I wanted something done right, I had to do it myself. I held it all the way until I had a panic attack and had to stop doing everything myself. I made changes, and you know what? I learned that being a solopreneur doesn't mean doing everything yourself. It means you own the business and work on your own terms — not that you personally execute every task. In this episode, I break down how to tell the difference, why "no one can do it like me" is a story we tell…
The Simplicity of Yellow Legal Pads [Friday Wrap-Up]
This week I talk about rediscovering the humble yellow legal pad after years (and hundreds of dollars) sunk into fancy notebooks and fountain pens. Then a piece by Kashmir Hill about discovering an AI-generated biography of herself for sale on Amazon that she never authorized or was contacted about, and a recommendation for the summer drinks series on Cocktails with Suderman. Plus this week's Automation of the Week: using Claude's Canva connector inside my Friday Wrap-Up skill to auto-generate the…
Why Your Solopreneur Business Feels So Complicated
One of my favorite shows is Scrubs, and there's one episode that's stuck with me for nearly 2 decades, and I think about it nearly every day. In it, the team can't diagnose a patient showing every sign of Lyme disease, because they can't find the tick bite. Every test comes back negative. Then Dr. Cox shaves the patient's head, finds the bite, and mentions Occam's Razor: the simplest solution is often the correct one. That idea has run through my whole business; I'm a natural overthinker. So today I…
Is Claude Winning? [Friday Wrap-Up]
This week I talk about whether Claude is quietly winning the AI war — at least among business owners and tech nerds — after every speaker at Ecamm Creator Camp reached for Claude and nobody mentioned ChatGPT or Gemini, and why its "constitutional" rule-following makes me more comfortable using it. Then my take on finishing The Odyssey (the Emily Wilson translation) on a plane into Chicago, and a look at my Five-CD Changer Playlist — the five-albums-only, no-shuffle rules that make it fun. Links: …
How Solopreneurs Stop Being the Content Bottleneck
Imagine making yourself a bowl of cereal. But instead of grabbing a bowl from the cupboard, you head to your backyard, throw a brand-new bowl on the pottery wheel, and while it dries, you drive to the store to buy a fresh box of cereal. Then you do the whole thing again the next morning. Sounds ridiculous, right? But that's exactly what we do with content when we create every piece from scratch with no ideas banked beforehand. So today I'm walking through how to stop being the bottleneck in your…
I almost did something horrible: get back in Instagram [Friday Wrap-Up] [Friday Wrap-Up]
This week I talk about almost re-joining a platform I know I'd hate. Then a look at Disney's next-gen audio-animatronic transforming from a pirate to a skeleton, and why it's a reminder that technology can still serve great storytelling. And a recommendation for the LEGO Game Boy set for a low-key long-weekend build. Plus, the Automation of the Week. Links: 2026 Summer and Fall Speaking Events I watched Disney's next-gen audio-animatronic transform from a pirate to a skeleton (TechRadar) LEGO Game…
I bought a tiny game controller for automation [Friday Wrap-Up]
This week I talk about my latest Mac automation tool: the 8BitDo Micro, a $15 tiny game controller I picked up during Prime Week and mapped to complex key combos and Raycast actions — and why these little tactile hardware automations are easier on your brain than memorizing keyboard shortcuts. Then a MacStories write-up that inspired the whole experiment, walking through real use cases for turning a game controller into a Mac input device. And a recommendation for New Rockstars' House of the Dragon…
Is speaking worth my time, Zuck doesn't get people, HotD [Friday Wrap-Up]
This week I talk about why this is my heaviest speaking year since before the pandemic — and how I'm deciding whether all that travel and prep time is actually worth it, given the real cost of crafting talks and getting clients from them. Then a story about Mark Zuckerberg telling Meta employees to "have fun again" after brutal layoffs, including the absurd perk of a permanent desk. And a recommendation for House of the Dragon Season 3, which drops June 21st. Links: My /now page Mark Zuckerberg…
You Can't Automate What You Can't Explain
Here's the problem: most solopreneurs don't know exactly what they do. They can't explain it, so they can't build systems around it. And when we try to build systems without explaining them, they end up with bad, ineffective systems. Because when we explain, we scrutinize. How do you fix it? Pick one task you do often, fire up a screen recorder, and narrate how you do it and why. Recording yourself doing your task is the blueprint. It is the plan. That's the first step to understanding the systems you…