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 131 Career: What's stopping you from going out on your own?!?
After 13 months away, the mic is back on—and we’re starting exactly where too many of us are stuck. In this raw and real return, Stephen unpacks the one conversation that’s been rising to the surface in every mentoring session, DMs, and late-night career spirals: Should I start my own thing? But the real question hiding underneath? Why can’t I bet on myself?This episode isn’t about logos, color palettes, or pitch decks—it’s about confronting the fear, vulnerability, and truth at the heart of every creative career pivot.
Whether you’re debating a freelance leap, building your own agency, or just trying to reclaim your voice in your next job, this one’s a mirror check.
What you’ll learn in this episode:
- Why most people ask the wrong questions about starting their own thing
- The emotional weight of discovering your personal brand
- How industry trauma erodes creative identity and confidence
- The difference between choosing your path vs. accepting what you’re given
- Why betting on yourself is terrifying—and totally worth it
Because there’s no “right time” to bet on yourself. There’s just now.
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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