The Crazy One

Ep 136 Career: Overcoming Fear and Insecurity: Why You Need a Plan, Not the Answers


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You’re stuck. Spinning in circles. Overthinking every move. Sound familiar? In this episode, Stephen breaks down the single most powerful piece of advice he gives to creatives, leaders, and anyone facing a moment of uncertainty: you don’t need the answer—you need a plan. When the road ahead feels overwhelming, this mindset shift can change everything. It’s not about having it all figured out. It’s about starting. This one’s for anyone who’s paralyzed by “what if” and needs a push to take the first step.

Stephen unpacks:

  • Why the beginning is always the hardest part
  • How creatives can reframe life and leadership as design challenges
  • The trap of overpreparing and waiting for certainty
  • Why great leaders lead with a plan, not perfect answers
  • How a bias toward action builds real confidence
  • The difference between stupid and crazy (hint: one of them has a plan)

Stop waiting for permission. Start building your plan. Then take the leap.

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The Crazy OneBy Stephen Gates

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