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.


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