In this episode, Rockne O’Leary sits down with Colin Masterson to talk about the winding path from athlete to accountant to strength coach, and the lessons that come from betting on yourself. Colin shares how leaving a stable accounting job to pursue coaching changed his life, what he learned from working long hours in strength and conditioning, and why he ultimately chose a career that felt more aligned with who he is.
The conversation digs into identity after sports, confidence, failure, and the pressure young athletes feel to follow a “standard” path. Rockne and Colin also compare their own experiences as college quarterbacks, the challenge of changing positions, and the value of sticking with a process even when it feels uncomfortable.
They also discuss youth sports, rec leagues, recruiting, and why kids should focus on playing where they can actually grow and compete. Colin shares how he now works as a coach in New York City, coaches both in person and online, and is in the process of opening his first boutique fitness studio.
Key topics covered
- Leaving accounting to become a strength coach
- Building confidence through failure and repetition
- Identity after football and life after athletics
- Why waiting your turn still matters
- The problems with youth sports pressure and over-specialization
- Building a business and personal brand
- The next chapter: coaching, entrepreneurship, and family
Memorable takeaways
- “Chasing edges” means constantly challenging yourself and growing.
- Confidence often comes from doing the work before you feel ready.
- Sports teach life skills that go far beyond winning and losing.
- It’s better to go where you’ll play and develop than chase status.
- Your identity should expand beyond one role, title, or season of life.
About Colin Masterson
Colin Masterson is a coach in the New York City area who works both in person and online helping clients build muscle, lose fat, improve performance, and train for races. He is also working to open his first boutique fitness studio while continuing to grow his personal brand online.
Colin Masterson:
YouTube:@ColinMasterson1
IG: @colinmasterson_
https://colinmasterson-fitforlife.lpages.co/fit-for-life-pu/
YouTube:@ColinMasterson1
IG: @colinmasterson_
Pocono Maple Water
Website: https://www.poconomaplewater.com/
IG: @poconomaplewater
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www.thevertigocentre.com