The Crazy One
The Crazy One is an award-winning podcast for creatives, leaders, and anyone who refuses to settle. Hosted by renowned designer and global design leader Stephen Gates, this show delivers unfiltered honesty, actionable insights, and hard-won wisdom to help you grow your creativity, lead with confidence, and build a meaningful career.
With over two decades leading world-class design teams at companies like InVision, Citi, Starwood Hotels, WW, and McCann Erickson, Stephen has built brands and digital experiences for clients including Disney, American Airlines, W Hotels, Verizon, Acura, and more — work that’s earned over 150 international awards and has been featured by Apple in 10 keynotes, 4 commercials, and the Human Interface Guidelines.
Now as the founder of CRZY, an independent strategy and design studio, he’s helping companies find bold new visions for their brands, experiences, and creative futures. Through The Crazy One, he shares everything he’s learned along the way — from integrating behavioral science with human-centered design to navigating imposter syndrome to building a career and creative life on your own terms.
With over 100 episodes and a loyal global audience, The Crazy One has been named:
• Webby Award Honoree for Best Technology Podcast
• #1 Podcast by Inside Design, HOW Design Live, and Springboard
• 5-star rated across every iTunes Store worldwide
This is more than a design podcast. It’s a wake-up call. A masterclass. A real-talk guide for finding your voice, owning your crazy, and changing the game.
No BS. No buzzwords. Just real insights from someone who’s been there.
The Crazy One
Ep 137 Career: The Pros and Cons of Going Out on Your Own
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.
SHOW NOTES AND MORE:
https://thecrazy1.com/
WATCH MORE CONTENT ON YOUTUBE:
https://www.youtube.com/@StephenGates
WORK WITH CRZY:
http://crzydesign.com/
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