Negative Convexity (Page 1)

Negative Convexity

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Latest — May 2, 2025

You Always Have a Card Left to Play

Even when it feels like we’re out of options, there’s always one card left to play—a relationship, a skill, or a small action that can move us forward. Taking that imperfect action not only keeps us in the game, it often reshuffles the deck and opens up new, unexpected possibilities.

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What Does a Good Business Feel Like? (Part 2 of 2)

A business with product/market fit doesn't necessarily feel good for an entrepreneur to work on. This note explores the factors internal to the entrepreneur that make a business feel worthwhile.

What Does a Good Business Feel Like? (Part 1 of 2)

Good and bad businesses feel different. What exactly is the difference? This post explores the external criteria--the market and customers--while next week's post explores the factors internal to the entrepreneur.

When You Are Bullied, Do You React with Fear or Anger?

A take on how countries might respond to the new U.S. tariffs, viewed through the lens of fear, anger, and shame.

Wasted Effort Is a Myth

People can sometimes feel paralyzed by the need to follow an optimal or efficient path towards a goal. But progress is uncertain. By focusing on what we learn at each step, we can mitigate the feelings of anxiety that come with any uncertain endeavor.

Why Every Creator Needs a “Stock” in Their Portfolio (Part 2)

Fulfillment in work requires a balance between the emotions of safety and excitement. We achieve this by building a portfolio of "bonds" and "stocks." From a place of safety, when the right opportunity presents itself, we can have the courage to go all-in on a home run opportunity.

Why Every Creator Needs a “Bond” in Their Portfolio (Part 1)

People assume that we need to go all-in on creative projects to make them work. However, that turns creative projects into life-or-death situations that must work for us to survive. Adding a stable, low-risk project to our portfolio is a better way to manage risk.

Why We Fixate on the Wrong Problems

People often mistake busywork for the important work that leads to real change. The important work is scary, especially because the initial feedback can be negative.

The Price of Playing a Real Game

Losses are a natural consequence of playing any game with a difficulty level appropriate to us. The key to long-term success is distinguishing between temporary losses and permanently destructive losses. When we hold on through the former and cut the latter, we win in the long-term.

The Cost of Optionality

"Keeping options open" is often times a disguise for avoidance and fear of commitment. If we never commit, we lose the chance to gain the compounding returns from choosing a course of action and sticking with it.