How to Actually Live the Life You're Optimizing For with Sahil Bloom

All the Hacks: Money, Points & Life

Chris Hutchins

Business, Society & Culture, Education, Self-improvement, Investing, Places & Travel

4.8 • 1.6K Ratings

🗓️ 25 March 2026

⏱️ 60 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

#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 Partner Deals Quince: Affordable luxury essentials with free shipping + 365 day returns Mercury: ⁠Manage, move, and grow your money LMNT: ⁠Free sample pack of my favorite electrolyte drink mix Fabric: ⁠Affordable term life insurance for you and your family MasterClass: ⁠Learn from the world's best with 15% off For all the deals, discounts and promo codes from our partners, go to: ⁠chrishutchins.com/deals Resources Mentioned Sahil: Website | Newsletter | X Wild Roman: 10% off with code CHUTCHINS10 Books & Articles The 5 Types of Wealth by Sahil Bloom A Reflection On The Little Things The Doorman Fallacy The Real AI Risk Nobody Told You About The 2028 Global Intelligence Crisis Rule for Life: Don't Complain AI Tools Deep Personality Lemon Wispr Flow 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 ⁠⁠Newsletter⁠⁠ | ⁠Membership⁠⁠ | ⁠X⁠⁠ | ⁠Instagram⁠⁠ | ⁠LinkedIn⁠⁠ Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

Click on a timestamp to play from that location

0:00.0	There is probably something in your life right now that you're optimizing, and there is a
0:03.8	decent chance that the optimization might be quietly destroying the thing you actually care about.
0:09.4	Today I'm talking with Sahel Bloom, writer, investor, and someone who actually caught himself
0:14.4	doing this and did something about it. He shares a concept called the Dorman Fallacy and why it
0:19.6	explains so much of what we get
0:21.5	wrong about our routines, careers, and even how we spend time with the people we love.
0:26.3	We'll get into why he moved his entire family to a new city after just one conversation with
0:30.8	his wife, how a lockbox fixed what willpower never could, and the six-word question he
0:36.7	uses when anxiety kicks in.
0:39.3	We'll also talk about why he thinks now is the best time in history to be a curious person
0:43.5	and why he put a bunch of his own money into a skincare company he named after his son.
0:49.4	I'm Chris Hutchins. If you enjoy this episode, leave a comment or share it with a friend.
0:53.3	And if you want to keep upgrading your money points in life, click follow or subscribe.
0:58.2	All right, Sahel, I know most of us realize at some point that we're only going to see our parents,
1:03.0	you know, a dozen or so times and we kind of feel guilty and we don't really do anything.
1:07.0	And for the second time in your adult life, you made a massive move.
1:11.4	Talk to me about how you made that move and how quickly and how easy it was.
1:15.4	My wife and I were living in the New York suburbs for the last four years.
1:20.0	This past summer, we drove up to Boston, which is where all of our family lives,
1:26.1	where we both grew up, my parents, her parents, my sister, our cousins, like everyone's up there. And we drove up to Boston, which is where all of our family lives, where we both grew up, my parents,
1:28.2	her parents, my sister, our cousins, like everyone's up there. And we drove up for her grandmother's
1:32.9	funeral. Her grandmother had lived in 95 years old. We went to the funeral. Everyone was there.
	...

Please login to see the full transcript.

Previous episode | Next episode

Disclaimer: The podcast and artwork embedded on this page are from Chris Hutchins, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Chris Hutchins and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.