Today is story time. And yes, it involves braces. But this isn’t really about teeth. It’s about the moment you realize your younger self would be absolutely blown away by the life you’ve built… Even if you don’t feel successful day-to-day. 

In this episode, I share a personal story that snapped me back into perspective, then break down the psychology that keeps high performers stuck in “the gap” and constantly chasing more.

You’ll leave with a simple reframe to feel proud of your progress, stop letting comparison run your goals, and start measuring success in a way that actually aligns with your values.

🎯 In this episode we riff on:

↠ Why getting braces again unexpectedly brought up old versions of me

↠ Growing up in poverty and what “success” used to feel like

↠ Working at Kinko’s, going to school full-time, and paying for everything myself

↠ The $8 burrito moment and what it revealed about survival-mode ambition

↠ The emotional contrast of paying for braces now without financial stress

↠ Why you don’t always feel successful when you become successful

↠ The trap of living in “the gap” and never looking backward

↠ Meeting your past self and recognizing the tenacity that built your current life

↠ How comparison erases perspective and fuels dissatisfaction

↠ A powerful money mindset insight from Morgan Housel

↠ Why money is a great tool, but a terrible servant when it’s used for status

↠ The deserted island test: Would you still want it if no one could see it?

↠ The 48-hour status boost (and why chasing it never ends)

↠ A grounding question to reset what you’re going after next

↠ Choosing goals based on values instead of optics

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