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The Grateful Podcast with Jack Wagoner
Episode 67
In this solo episode of The Grateful Podcast, host Jack Wagoner dives deep into why we make the decisions we make, challenging the common belief in human rationality. Drawing from insights in The Undoing Project by Michael Lewis and the groundbreaking research of Daniel Kahneman and Amos Tversky, Jack questions whether logic and reason are really guiding our behavior—or if we’re missing something deeper.
He shares a vulnerable personal story of choosing between Harvard and Northeastern and explains why trusting his gut feeling led him to a more expansive, fulfilling decision. This episode explores themes of behavioral psychology, intuition, self-examination, and how to build a life based on internal truth rather than external validation.
📚 Referenced:
• The Undoing Project by Michael Lewis
• The work of Daniel Kahneman and Amos Tversky
• Socratic wisdom: “The unexamined life is not worth living”
🎧 Listen if you’re curious about:
• Why most of us don’t actually understand our decisions
• How intuition may be more trustworthy than logic
• The self-fulfilling prophecy of rationality
• Letting go of needing to explain your choices to others
• Designing a life based on inner fulfillment, not prestige
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⏱️ Chapters & Timestamps:
0:00 – The Illusion of Rational Decisions
1:24 – Introducing The Grateful Podcast & Jack’s Passion
2:40 – The Undoing Project & the Irrationality of Economics
5:12 – Thought Experiment: Gains vs. Losses
7:00 – The Problem With Over-Rationalizing
8:47 – Sponsored Segment: SweetDash
10:00 – Examining What You Can Control
11:36 – The Harvard vs. Northeastern Decision
14:10 – Trusting Gut Feelings vs. External Validation
16:03 – The Power of Subjective Evidence
17:28 – Temper Tantrums & Learned Behavior
18:52 – The Trap of Needing an Explanation
20:00 – Final Thoughts: Examine Your Behavior
21:30 – Mother’s Day Reminder + Outro
📺 Watch the full episode or listen on your favorite platform:
Spotify/Apple: https://podcasts.apple.com/us/podcast/the-grateful-podcast-with-jack-wagoner/id1725776061
Subscribe for more deep conversations with thinkers, seekers, and soulful creators. 🙏
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🧠 More from Jack:
Newsletter (Magic, Meaning & Momentum): https://magic.beehiiv.com/v1/aa6b0945-43aa-43c8-b320-0fde6998f852?email=%7B%7Bemail%7D%7D
Instagram: https://www.instagram.com/jack_wagoner_/
1:1 Coaching & Dream-Chasing Guidance: [email protected]
💬 If you found this conversation meaningful, send it to a friend and leave a review. It really helps more people find this kind of soul-nourishing content.
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🎙️ About Jack:
I’m an 18-year-old high school student with a big dream: to show the world that you can be grateful and ambitious at the same time. Through The Grateful Podcast, I explore what it means to live a meaningful life—one deep conversation at a time.

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