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.
Regret minimization framework for creators
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Hey Reader, Do you ever feel pulled in multiple directions and unsure of which goals to pursue? I found myself in this exact situation recently, trying to balance expanding Kit Studios to new cities, scaling Kit's app store, designing new features, writing a book, and building my personal brand. During a session with my coach, Dan, he asked me a question that cut through all the noise: "If you knew for sure you couldn't accomplish all of your goals, which would you most regret not achieving in the next 5–10 years?" This question is part of what's called the Regret Minimization Framework—and my answer surprised me. I immediately said writing books. This caught me off guard, because I would have assumed growing Kit would be at the top of my list. But upon reflection, it made perfect sense. While I obviously want Kit to continue growing, I'm proud of what we've built. The idea of not publishing any new books in the next five years feels like a bigger potential regret. When I compared two potential futures—one where Kit grows to $100M but I publish zero books vs one where Kit only reaches $50-60M but I publish a book—I realized I'd feel worse about the first scenario. Why does writing books matter so much to me? When I wrote essays like The Ladders of Wealth Creation or first talked about how making money is a skill, I thought about what my 15-year-old self would have wanted to read. But now, my perspective has shifted: I'm writing for my son, Oliver, who will soon be 15 himself. Writing for my son feels more meaningful because:
This clarity showed me that I need to build a real system for writing books—one that involves other smart people helping me—to ensure it actually happens. The Regret Minimization Framework can be a powerful tool when you’re struggling with where to focus your limited time and energy. It helps you identify what truly matters to you. To use it yourself, ask: "Among all the things I want to accomplish, which would I most regret not doing if I looked back 5–10 years from now?" The answer might surprise you. But that surprise often reveals what's truly important. What would you most regret not accomplishing in the next 5–10 years? Take a moment to consider this question. It just might change where you focus your creative energy. PODCASTHow To Scale From 500K To $2M (Coaching Session)Today I’m joined by Jay Singh for a coaching session to map out how he can scale his product studio, Casper, from $500K to $2M in annual revenue—without growing a huge team or sacrificing profit margins. We dive into ideal client profiles, packaging services for predictable revenue, and how Jay can use LinkedIn to consistently generate high-quality leads. You’ll hear us cover:
Watch or listen to episode » COMEDYHasan Minhaj: Off With His HeadHasan Minhaj's latest Netflix special is somewhat polarizing (it debuted just before the election), but it's fantastic. He takes shots at every political group equally, which is pretty rare these days. Nobody gets a pass, and that's what makes it so refreshing to watch even if you don't agree with everything he says. The whole thing feels like a work of art rather than just a comedy special. KEYNOTEKit featured in Figma product launch keynoteFigma announced some great new updates at their Config 2025 conference last week—Figma Site, Shape Builder, Figma Draw, and more. But the coolest part was seeing Figma highlight Kit designs from our rebrand during their keynote. Have a great week! —Nathan |
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.
Hey Reader, If I could solve only one thing in my business, that would have the biggest impact, what would that be? This is the question every great entrepreneur obsesses over. Rather than trying to do everything at once, you look for the bottleneck and focus on solving that. There’s a book called The Goal by an Israeli physicist named Eliyahu Goldratt. It’s a 1984 business novel that business systems nerds love. However if you’re not a business systems nerd you probably… won’t love it. It’s...
Hey Reader, Have you ever spent money on something and immediately felt guilty afterward? Will Guidara spends his money foolishly on purpose. And he thinks you should too. He once bought an entire barrel of whiskey and put it in his basement. He also put a skee-ball machine in the office. Is he going to get a monetary return on either of these things? No. But that’s kind of the point. He calls it the 95/5 rule: Manage your money and time like a maniac 95% of the time (no expense is too...
Hey Reader, Have you ever spent a whole day on something almost nobody saw? It's painful when the whole reason you worked hard was because you wanted to reach people. If you teach a workshop in person, you reach the 20 people in that room. But if you record that same workshop once, you can keep teaching for years on autopilot. This is the concept of leverage, and it's something I talk about in my upcoming book, The Ladders of Wealth (you can pre-order it now). A lot of people will look back...