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BRAVE • FOCUSED • BRILLIANT The Making of a "Dirtbag Billionaire" The founder of Patagonia made a fortune, and now he's giving it all away. Here's what we can learn as leaders and creative pros from his experience.

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What if your "calling" is less a needle in a haystack and more like noticing that the hay is starting to itch?

In this week’s Daily Creative episode, I had the pleasure of interviewing David Gelles, NY Times journalist and author of Dirtbag Billionaire, to explore the paradoxical journey of Yvon Chouinard—the reluctant billionaire behind Patagonia. We dug into the story of someone who never set out to change the world, but did so by paying careful attention, staying true to his principles, and making hard choices when profit and purpose collided.

Here are five lessons (or reminders) that stuck with me:

1. Your calling is revealed through what bothers and excites you​
It’s tempting to think purpose is found "out there", after enough networking or another assessment. But most often, it’s uncovered by noticing repeated themes—the tensions, the things you love, and the things that drive you crazy. Yvon Chouinard’s story is one of stumbling into deeper contribution by staying awake to the discomforts and passions embedded in his daily work. If you’re feeling restless, paying closer attention to what sparks frustration or curiosity could be the compass you need.

What patterns—of energy, annoyance, or excitement—keep showing up in your life or work?

2. Radical decisions require inconvenient awareness​
Patagonia’s most defining moments weren’t scripted business moves; they started with Chouinard noticing the impact of his own products and refusing to ignore it. Stopping the sale of damaging equipment, even at massive financial risk, wasn’t about strategy—it was about refusing to tune out the ripple effects of his work. Staying awake, even when it threatens comfort, is what separates meaningful leadership from habitual achievement.

Where are you glossing over second- or third-order impacts in favor of efficiency or tradition?

3. Principle matters more when profit is at stake​
It’s easy to tout values until they threaten the bottom line. Patagonia repeatedly chose environmental integrity over profit—from cutting the piton business to investing in expensive organic cotton and less harmful waterproof materials. That willingness to let values cost you is rare. True values aren’t what’s printed on the wall; they’re the sacrifices made when money’s on the table.

When did you last make a costly decision, for no other reason than it was the right thing to do?

4. Success brings paradox, not easy answers​
Chouinard became everything he distrusted: a billionaire and business icon, despite his aversion to money and conventional metrics. Enduring paradox—supporting activism while running a polluting company, leading with integrity but facing tough social critiques—is unavoidable. The aim isn’t perfection, but showing up, acknowledging these tensions, and recalibrating whenever you've drifted off-course.

What contradictions in your own work or leadership are asking for honest attention instead of avoidance?

5. Compound interest applies to values, too​
Every small act of aligning your work with your principles builds into something significant over time, much like money accrues. Patagonia’s half-century of values-led choices didn’t just shape a company—they shaped movements and lives. The impact compounds quietly, especially from the hardest decisions made faithfully and consistently, not just when convenient.

In what small, repeatable way can you choose integrity over expedience this week?

Every time you choose to align your actions with what you value—even in small ways—you’re investing in a legacy that will outlive you. You make echoes.

Meaning isn’t found or inherited; it’s grown—one awake, honest choice at a time. Stay brave, focused, and brilliant. Your marks matter, even when you’re not quite sure anyone’s noticing.

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​ Todd Henry teaches leaders and teams how to be brave, focused, and brilliant. He is the author of seven books, and speaks internationally on creativity, leadership, and passion for work. ​TODDHENRY.COM​ ​​​​​

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