The Crazy One

Ep 137 Career: The Pros and Cons of Going Out on Your Own


Listen Later

After decades inside the system—agencies, in-house, and everything in between—Stephen Gates made the leap. No roadmap. No safety net. Just a decision to bet on himself. Three years later, he’s pulling back the curtain on the truth behind the leap: the real risks, the unexpected wins, and the power in finally doing work that feels like yours.

This episode isn’t a glorified founder story. It’s a raw, honest reflection on what happens when you walk away from the broken systems and build something with your own two hands. From burnout and layoffs to reclaiming creativity and control, Stephen breaks down the mindset shifts and hard-earned lessons that have shaped his journey—and why this moment might be your moment too.

You’ll learn:

• Why chasing validation in job interviews is a losing game

• How Stephen reframed fear into freedom (and how you can too)

• The unsexy business truths no one tells you about freelancing

• Why knowing what you actually want is everything

• The emotional weight of owning your failures—and your wins

• How to recognize when it’s time to stop surviving and start building

This is not about overnight success.

It’s about reclaiming your voice, your value, and your vision. Bet on yourself—just make sure you’re ready to do the work.

Send us a text

SHOW NOTES AND MORE:
https://thecrazy1.com/

WATCH MORE CONTENT ON YOUTUBE:
https://www.youtube.com/@StephenGates

WORK WITH CRZY:
http://crzydesign.com/

FOLLOW THE CRAZY ONE:
LinkedIn, Instagram, Facebook

...more
View all episodesView all episodes
Download on the App Store

The Crazy OneBy Stephen Gates

  • 4.9
  • 4.9
  • 4.9
  • 4.9
  • 4.9

4.9

415 ratings


More shows like The Crazy One

View all
Daily Creative with Todd Henry by Todd Henry

Daily Creative with Todd Henry

516 Listeners

This American Life by This American Life

This American Life

90,847 Listeners

Planet Money by NPR

Planet Money

30,727 Listeners

Design Matters with Debbie Millman by Design Matters Media

Design Matters with Debbie Millman

1,230 Listeners

Freakonomics Radio by Freakonomics Radio + Stitcher

Freakonomics Radio

32,087 Listeners

Hidden Brain by Hidden Brain, Shankar Vedantam

Hidden Brain

43,347 Listeners

Acquired by Ben Gilbert and David Rosenthal

Acquired

4,196 Listeners

The Futur with Chris Do by The Futur

The Futur with Chris Do

848 Listeners

Creative Confidence Podcast by IDEO U

Creative Confidence Podcast

127 Listeners

Design Better by The Curiosity Department, sponsored by Wix Studio

Design Better

323 Listeners

Worklife with Adam Grant by TED

Worklife with Adam Grant

9,162 Listeners

NN/g UX Podcast by Nielsen Norman Group

NN/g UX Podcast

106 Listeners

Hard Fork by The New York Times

Hard Fork

5,447 Listeners

The Economics of Everyday Things by Freakonomics Network & Zachary Crockett

The Economics of Everyday Things

1,610 Listeners

HBR On Leadership by Harvard Business Review

HBR On Leadership

155 Listeners