Regret minimization framework for creators

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:

It's focused on someone I deeply care about
It's forward-looking rather than revisiting the past

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.

PODCAST

How 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:

How to attract the right customers
How to build predictable, recurring revenue
Building a business that supports the life you actually want

Watch or listen to episode »

COMEDY

Hasan Minhaj: Off With His Head

Hasan 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.

View on Netflix »