The Inner Game of Entrepreneurship
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On Failure & Resilience
The Stockdale Paradox: holding high and low expectations simultaneously.
Soldier James Stockdale observed that the most optimistic prisoners often fared the worst. Outstanding founders believe their success is inevitable, while expecting—even relishing—failures along the way.
“Failure is not something that happens at one point in time. Failure is a door. To me failing feels like stepping out of a room, and into a new one. There is continuity with failure; the end of something always means the start of something else.”
Anything worth doing requires doing things wrong first to learn to do them correctly eventually.
“Just because something doesn’t do what you planned it to do doesn’t mean it’s useless.”
Post-it notes, microwaves, Viagra, Play-Doh—many modern inventions were initially intended to solve another problem. Edison was keen to challenge his own flawed assumptions.
You overestimate how bad failure will feel and how long it will hurt.
People systematically overestimate the intensity and duration of negative emotions from bad outcomes. Founders who understand this can take bigger risks knowing recovery is faster than anticipated.
On Identity & Purpose
“I am also all of what I’ve lost.”
Paul Van Doren reflected on outliving his wife, friends, and business partners. Your success won’t shield you from loss. What remains isn’t just what you built—but who you became in the process.
“Imagine you are building a Jenga tower: the higher you stack expectations, the more unstable your identity becomes as a whole.”
The higher the expectations you place on yourself, the harder it becomes to experience satisfaction in who you are at this moment.
“No dream is as great as the person you might become by remaining true to it.”
The best goals center on becoming, not doing or having. The most rewarding aspects of reaching your goal lie in your chance at improving, each step of the way.
“How you climb a mountain is more important than reaching the top.”
— Yvon Chouinard
This philosophy shaped Patagonia’s most consequential decisions, from choosing ethical manufacturing partners to rejecting shortcuts that boost short-term profits.
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