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Nathan Barry

I'm a designer who turned into a writer who turned into a startup CEO. My mission is to help creators earn a living. Subscribe for essays on building an audience and earning a living as a creator.

Featured Post

What if I bought your business

Hey Reader, Imagine someone bought your business tomorrow. What's the first thing they would change? Maybe they'd raise prices. Or fire that team member who's been dragging things down. Would they automate the task you've been doing manually for years? Hire for the role you keep saying you'll fill eventually? When I ask creators this question, they usually know the answer immediately. They don't even need to think about it. The answer is already sitting there, waiting. You probably know what...

Hey Reader, "I will write 1,000 words every day." That's the commitment I made in 2012 that changed my life. I ended up writing 100,000 words in 100 days and went on to write 266,000 words in a year. I wrote every day for nearly two years before finally breaking the chain. Writing consistently continues to be one of the most important habits of my career. So when my coach asked me what I'd regret not doing the most if I imagined my life 5 to 10 years from now, my answer surprised me: writing...

Double-Axis Reality

Hey Reader, Would you rather improve your fitness or spend time with family? This looks like a reasonable question, but it's actually a false dichotomy. The question assumes you have to choose between two things that aren't actually in opposition. You've heard of false dichotomies, but there's a subtler version of this trap that I call the Single-Axis Fallacy—where we accept that both options exist but wrongly assume that having more of one means less of the other. The reality is that fitness...

Video: The Flywheel Concept That Will Change Your Business

Hey Reader, Remember when you first started your business and it felt like a game? You couldn't wait to wake up and work on it. But some days, you dread waking up because everything feels overwhelming—the opposite of what you started out to build. I just released a new video I've been working on that shows you exactly how to get back to that excitement using flywheels. Here's what I break down on the board: The 3 laws that make flywheels work (in real life physics and business) How one...

Podcast recording flywheel

Hey Reader, Remember when you first started your business and it felt like a game? You couldn't wait to wake up and work on it. Now it's just constant stress and putting out fires. I felt this way about my podcast. I love having deep conversations with creators I admire, but the weekly production was taking over my life. As the CEO of Kit, I spend most of my time building and growing the company—I couldn't dedicate entire days every week to podcast recording. Something had to change. I needed...

video preview

Hey Reader, If you're reading this, you probably have years of expertise in your field. You see inefficiencies everywhere that you could fix. Creating a course or consulting service to share what you know feels like the logical next step. But here's what happens when you start building: You spend months crafting your course or service, polishing every detail. Then you try to find people who want to buy it. This approach puts you in the position of convincing people they have a problem rather...

Farmer to horse: “You won’t lose your job to a tractor, but to a horse who learns how to drive a tractor.”

Hey Reader, What happens when AI gets better at what you do? You've probably heard people say, "AI won’t take your job, but someone who knows how to use AI will." I actually think AI will take your job. And mine too. But more on that in a minute. I mentioned a couple weeks ago that there are no more long careers. Careers used to last a lifetime. Now they might be more like 10 months. So how do you make yourself valuable at work? More essential? No matter what role you're in, you need to think...

Hey Reader, I used to be very consensus driven. Every decision at Kit required input from everyone. I'd collect opinions in endless meetings, because I care about harmony and making sure every voice was heard. The problem was nothing was getting done. My coach asked me one question that changed everything: "If you were CEO, what would you do?" It sounds simple, but it hit me like a truck. I am the CEO, yet I was acting like I needed permission to lead my own company. I realized I'd been...

Hey Reader, Careers used to last a lifetime. Then they dwindled to 10 years. Now it might be more like 10 months. If you're young and starting out, this reality can feel overwhelming. What advice can possibly make sense in a world that's changing this fast? This is something I think about a lot with my oldest turning 14 in a few weeks. What career advice should I give him? Focus on what doesn't change Jeff Bezos built Amazon on this principle. He knew that no matter what technology emerged,...

Bookshelves are overflowing with colorful books.

Hey Reader, You ever wonder how some people just seem to speak in perfect soundbites? They always have the right thing to say, delivered in exactly the right way. At our Craft + Commerce conference this summer, Tristan de Montebello from Ultraspeaking taught something called "The Accordion Method"—a technique for learning to speak this way by compressing your thoughts down to 30 seconds, then expanding them back up to 2 minutes. Watching creators practice this made me think: Most of us are...