Welcome to Episode 51 of The HockeyStick Show. I’m Miko Pawlikowski, and this week I sat down with Tommy Breedlove (the author of the book “Legendary”) to talk about the long road from survival mode to self-worth, and how money, identity, and purpose get tangled together along the way.
Tommy shared his personal story, from growing up around addiction and incarceration to building a successful career, losing himself inside of it, and ultimately redefining what “success” actually means. The conversation moved fluidly between money, masculinity, relationships, and the quiet damage caused by chasing external validation.
Money, Identity, and the Cost of Approval
Tommy started by unpacking how early trauma and instability shape our relationship with achievement. For him, success became a shield. Money, status, and performance were ways to feel safe, respected, and untouchable.
He explained how this pattern shows up for many high performers, especially in tech and business. On the surface, things look great. Underneath, there is burnout, resentment, and a constant fear of being exposed. The more approval you chase, the more expensive it becomes to maintain the image.
When Net Worth Becomes Self-Worth
We spent time digging into how money quietly becomes a proxy for value. Tommy talked about how easy it is to confuse financial success with identity, and how that mindset erodes relationships, health, and joy over time.
He challenged the idea that more is ever enough when the underlying wound is unresolved. Without self-respect, success only amplifies insecurity. With it, money becomes a tool instead of a scoreboard.
Redefining Success on Your Own Terms
The conversation shifted toward what it actually takes to step off the treadmill. Tommy described slowing down, setting boundaries, and getting honest about what you want rather than what you think you should want.
That process often involves hard tradeoffs. Letting go of roles, relationships, and expectations that no longer fit. Learning how to say no. Building a life that feels aligned, even if it looks smaller from the outside.
At its core, this episode was about sustainability at a human level. How to build a career without losing yourself. How to pursue ambition without outsourcing your self-worth. And what success looks like when nobody is watching.
Thanks for listening!
