How to Actually Live the Life You're Optimizing For with Sahil Bloom
All the Hacks: Money, Points & Life
Fear Setting for Better Decisions
Sahil Bloom describes writing down fears, deconstructing them, and using AI to argue the optimistic case before making a major life decision.
#271: Learn why over-optimizing your life can quietly destroy the things you actually care about. Chris and Sahil explore the doorman fallacy, why big life decisions should happen fast, how to use AI as a thinking partner, and why systems beat motivation every time.
Sahil Bloom is a writer, entrepreneur, and investor. He wrote The 5 Types of Wealth, publishes the newsletter The Curiosity Chronicle to nearly a million readers, and is the Founder of the men's skincare line Wild Roman.
Link to Full Show Notes: https://chrishutchins.com/sahil-bloom-stop-over-optimizing-life
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Resources Mentioned
Sahil: Website | Newsletter | X
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Books & Articles
AI Tools
Phone Lock Box: Mindsight Timed Lock Box
Full Show Notes
(00:00) Introduction
(00:58) Why Sahil Moved His Entire Family from New York to Boston
(03:09) Why Big Life Changes Should Happen Fast
(04:47) The Real ROI of Small Moments
(06:27) The Doorman Fallacy: What You Lose When You Optimize the Surface
(10:32) Designing Your Life vs Letting It Happen
(15:15) The Tradeoffs of Living Near Opportunity
(22:17) Why Now Is the Best Time in History to Be Curious
(30:05) How Sahil Actually Uses AI Day-to-Day
(36:23) Solomon's Paradox: Why We Can't Take Our Own Advice
(38:45) Using Voice Agents to Think Better
(40:03) Balancing Work, Family, and Time
(45:47) Why Motivation Is Overrated and Choice Architecture Wins
(49:11) Making Workouts Non-Negotiable Without Sacrificing Work
(52:54) How Often to Audit Your Routines (Before They Start Owning You)
(53:42) Why Sahil Invested $1M of His Own Money in a Skincare Company
Connect with Chris
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