Every December, I revisit the sketch that reshaped my business. Twenty years ago, frustrated with the wrong kinds of clients, I drew a simple matrix to help me sort out what was really worth my time. That sketch turned into a powerful tool I’ve shared with thousands of solopreneurs. I bring it back every year to help you plan the next one with more clarity, more purpose, and ideally, more joy. Meet the Money-Fun Matrix The Money-Fun Matrix is a simple 2x2 tool I created to evaluate the...
14 days ago • 3 min read
Hey, Reader — Have you ever pinned your self-worth to a single number? Mara did. She wasn’t new to baking, and she’d built a loyal market following. But still, every week, she let one number decide if she was a failure. Each Saturday, Mara rolled into the farmers’ market before sunrise. She displayed warm sourdough. Rosemary focaccia. Cinnamon raisin loaves. Every loaf reflected the precision and care of a serious professional baker. And every Saturday at noon, she judged her entire business...
21 days ago • 3 min read
Most people try to avoid failure. Paul MacCready, however, was different. He welcomed it. For nearly two decades in the 1960s and 70s, the world’s best engineers chased a dream. Their goal? Build a human-powered aircraft that could fly a mile-long figure-eight and clear a ten-foot barrier. No one could do it. The failure pattern was consistent. Teams built immaculate, over-engineered planes. A single crash meant months of repairs. With that much sunk into every prototype, experimentation...
28 days ago • 3 min read
In the early 1980s, Steve Jobs’ team at Apple Computer was creating the revolutionary computer that would become the Macintosh. They knew that a crucial part of creating a personal computer “for the rest of us” would be visual symbols instead of arcane computer code. So Andy Hertzfeld called up Susan Kare, a former high school artist chum (Weak ties! See the recent issue), and told her to go get the smallest graph paper she could find. Kare’s task was deceptively simple: make the computer...
about 1 month ago • 2 min read
Hey, Reader — Do you have favorite products you can’t live without? For me, it’s my Dyson hair dryer, vacuum cleaner, and room fan. Silly, I know. People think they’re incredibly overpriced. But I bought them all for one reason: every Dyson product delivers a remarkable experience. And they’re more alike than you might think. You see, many folks think Dyson built a vacuum company. He didn't. He built a company obsessed with one underlying mechanism: how to move air with precision. Everything...
about 1 month ago • 3 min read
Could your next big break start with a stranger? That’s exactly how things unfolded for a then-unknown chef named Anthony Bourdain. Back in 1999, Bourdain thought he was writing for a handful of cooks when he penned his behind-the-scenes article about restaurant operations. Maybe his fry cook would laugh, he thought. Maybe he’d make a hundred bucks. He sent his essay, “Don’t Eat Before Reading This,” to a small New York City alt-weekly that ended up killing it at the last minute. But it...
about 2 months ago • 3 min read
With Black Friday approaching, the pressure to launch something (anything!) is everywhere. But not every idea is ready to bloom. Some are still underground, quietly developing roots, waiting for the right season to flourish. If you’ve worked solo long enough, you’ve seen this pattern: the idea that felt too big, too early, or too complicated circles back years later. When it returns, it’s clearer, sharper, and better aligned with who you’ve become. Ideas have their own pace. Some sprint,...
about 2 months ago • 3 min read
A lot of content you breeze past. Some stops your scroll. But every so often, a visual comes along that doesn’t just explain an idea, it locks it in your brain. Kyle Adams’ Warm Growth matrix is one of those rare visuals. In a single 2x2 chart, it captures his philosophy of “Warm Growth,” a mindset that favors resonance over reach, and connection over clout, when building an audience. It doesn’t just tell you what Kyle believes, it shows you. This is what makes it a signature framework: a...
2 months ago • 3 min read
Hey, Reader — It was 32 years ago this past week when I walked into a bookstore and saw Working Solo on the shelf for the first time. I can still picture the cover and the quiet thrill of holding a physical idea that had lived in my head for years. For a LinkedIn post, I snapped this photo with two cupcakes to celebrate 32 years. At the time, I thought I was writing a book. What I didn’t know was that I was launching an idea that would ripple far beyond me. Back then, self-employment was seen...
2 months ago • 3 min read