Deep Thoughts With Michelle Handy

Discomfort is the Cost of Fulfillment – A Conversation with Stephen Gates

Michelle Handy

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In this episode of Deep Thoughts with Michelle Handy, I sit down with Stephen Gates, founder of CRZY design studio and host of The Crazy One podcast. Stephen was my first mentor outside academia, and his advice has shaped how I approach my career, creativity, and leadership. We unpack the power of discomfort, the importance of asking the right questions, and why showing up authentically might just be the most rebellious thing you can do in your career.

Episode Highlights

  • Navigating the discomfort that often precedes fulfillment
  • Recognizing the signs that it’s time for a career shift
  • Balancing authenticity and ambition in corporate environments
  • Why success only makes sense in hindsight
  • Building a career path that aligns with your values and strengths

Practical Frameworks Discussed

  • Design Thinking for Your Career – Prototype, test, refine. Don’t wait for clarity—build it.
  • Three-Word Exercise – Ask trusted people to describe you in three words. Look for patterns to uncover strengths and blind spots.
  • The Balance Between Discomfort and Confidence – How to stay uncomfortable enough to grow, but not so much that you become paralyzed.

Books and Resources Mentioned

About Stephen Gates
Stephen Gates is the founder of CRZY design studio and the host of The Crazy One podcast. With leadership experience at InVision, Citi, Starwood Hotels, and WeightWatchers, Stephen has led design teams responsible for globally recognized campaigns and innovative products. His work has earned over 150 international awards and has been featured in Apple keynotes and design guidelines.

Connect with Stephen

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Have thoughts about this episode? Connect with Dr. Michelle Handy on LinkedIn and follow Deep Thoughts for more insights at the intersection of behavioral science, tech, and design.

Deep Thoughts with Michelle Handy explores the intersections of behavioral science, tech, and design through engaging conversations with thought leaders. Whether you're building products, leading teams, or navigating your own career journey, each episode delivers practical insights to inspire personal growth and drive innovation.