When Could Chris Have Retired?

Chris recounts his financial-planner moment realizing he could have retired and how that prompted rethinking work purpose.

Play episode from 05:17

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Transcript

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Transcript

Episode notes

In this episode, Chris Do sits down with Jodie Cook for a wide-ranging conversation about playing the long game in business, relationships, and life. They unpack the difference between short-term wins and infinite games, emphasizing why building something you never want to sell leads to deeper fulfillment and clarity. Chris reflects on his own journey through financial security, meaning, and redefining success beyond money.

Together, they explore how scarcity thinking shapes decisions and why authenticity compounds over time. The discussion sets the foundation for choosing purpose-driven work that can sustain decades, not just seasons.

Timestamps

(00:00) — Intro

(05:56) — Discovering financial security changes motivation entirely

(10:31) — Why pursuing meaning creates money naturally

(15:24) — Letting go of outcomes to regain creative freedom

(21:37) — How childhood patterns shape adult decision making

(28:12) — The danger of living for others’ expectations

(34:48) — Why mastery requires long-term commitment and patience

(41:26) — Redefining success beyond traditional career milestones

(48:55) — Teaching children autonomy, respect, and resilience

(56:34) — Breaking scarcity mindset through intentional life design

(01:04:12) — Building a life you never want to retire from