The Futur with Chris Do

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Playing the Long Game in Business and Life w/ Jodie Cook | Ep 416

Jan 29, 2026

Guest

Jodie Cook

Jodie Cook, entrepreneur, author, and speaker focused on long-term strategy and personal growth. She and Chris explore playing the long game in business and life. They contrast short-term wins with infinite games. They discuss scarcity mindset, authenticity compounding over time, and designing a life you never want to retire from.

01:15:24

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ADVICE

Build Something You Never Sell

Design a business you never want to sell and be prepared to do it forever.
Remove the need to chase money first and focus on meaning; money often follows purpose.

question_answer

ANECDOTE

Retirement Revealed By A Spreadsheet

Chris learned from his financial planner that he could have retired earlier than he thought.
That realization freed him to pursue work for meaning rather than necessity.

insights

INSIGHT

Meaning Amplifies Money

Once financial pressure drops, motivation shifts from earning to meaning.
Pursuing meaning creates money naturally because value compounds over time.

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Playing the Long Game Defined

01:49 • 44sec

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Chris on Financial Security Shifting Motivation

02:33 • 3min

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When Could Chris Have Retired?

05:17 • 3min

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Scarcity Mindset and Meaning Over Money

08:10 • 3min

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Passion vs. Execution

11:05 • 3min

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Control, Clarity, and Serving Your Audience

14:34 • 2min

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Living for Others' Expectations

16:19 • 2min

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Teaching Children Autonomy and Questioning

18:18 • 1min

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Parenting Principles and Non-Negotiables

19:25 • 2min

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Family Patterns Shape Adult Choices

21:36 • 13min

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Role-Play: Teaching Resourcefulness

34:51 • 8min

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Deciding Early Versus Experimenting

43:17 • 8min

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Rehearsing the Future and Commitment

50:52 • 3min

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Stacking Skills to Become Non-Fungible

53:27 • 9min

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Playing to Win vs. Infinite Game

01:02:15 • 4min

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Setting Boundaries to Do Your Best Work

01:05:46 • 7min

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Consistency, Trust, and Unignorable Work

01:13:07 • 2min

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Graveyard of Broken Dreams Warning

• Mentioned in 38 episodes

How to Fail at Almost Everything and Still Win Big

Kind of the Story of My Life

Scott Adams

In 'How to Fail at Almost Everything and Still Win Big,' Scott Adams shares his personal story of numerous failures and how he transformed them into lasting successes. Adams challenges conventional career advice by advocating for systems over goals, emphasizing the importance of personal energy, and highlighting how a combination of mediocre skills can be surprisingly valuable. He recounts his experiences in the corporate world, his inventions, investments, and other ventures, offering practical tips such as prioritizing creative work, managing attitudes, and using affirmations. The book is filled with humor and valuable insights into human psychology and the role of luck in achieving success.

#1426

• Mentioned in 26 episodes

The Squiggly Career

Sarah Ellis

Helen Tupper

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