The Crazy One

Ep 135 Career: The Hidden Problem of ‘Experience-ism’ in Creative Careers


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When the stakes are high—new job, big idea, career leap—most of us freeze. We stall, waiting for the “right” moment, the perfect answer, the foolproof plan. But in this episode, Stephen shares the raw truth behind what holds us back—and the simple mindset shift that sets real leaders apart. It’s the advice he gives in almost every mentoring session. The one thing that changes everything.

Because leadership isn’t about knowing it all. It’s about starting before you do.

In this episode, you’ll learn:

  • Why most people get stuck at the starting line—and how to break through it
  • The difference between a plan and an answer (and why that matters)
  • How to apply design thinking to your career and decisions
  • What a “bias towards action” really looks like in practice
  • Why confidence comes after the leap—not before it

This one’s for anyone standing at the edge, waiting for certainty. Spoiler: it’s not coming. But you are more ready than you think.

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The Crazy OneBy Stephen Gates

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