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

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

Author: Chris Hutchins March 25, 2026 Duration: 56:41
#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

Ever feel like there's a smarter, more efficient way to navigate your finances, your travels, and your daily routines? That's the core question driving All the Hacks: Money, Points & Life. Hosted by Chris Hutchins, this podcast is built on a simple, powerful idea: maximizing value doesn't mean sacrificing enjoyment. Instead, it's about the strategic choices that free up resources-both money and time-for what truly matters. Chris approaches life as a series of systems to be optimized, drawing from his own experience saving millions through meticulous analysis. The conversations here are practical and wide-ranging, moving seamlessly from credit card points strategies and investment philosophies to the less tangible hacks for personal fulfillment. You'll hear from a diverse roster of experts and icons, including Tim Ferriss, Tony Hawk, Codie Sanchez, and Gary Vaynerchuk, who all bring their unique perspectives on building wealth and designing a compelling life. Each episode feels like a focused workshop, offering actionable advice you can use immediately, whether it's planning a luxury vacation for a fraction of the cost or rethinking your approach to career and leisure. This isn't just about frugality; it's about unlocking freedom and excitement through smarter decisions. Tune in for a consistently insightful blend of tactical moves and deeper conversations that challenge the conventional trade-offs between spending, saving, and living well.
Author: Language: English Episodes: 100

All the Hacks: Money, Points & Life
Podcast Episodes
The Simple Path to Wealth and FU Money with JL Collins [not-audio_url] [/not-audio_url]

Duration: 1:09:43
#194: Build wealth and achieve financial freedom with three simple, actionable steps. Personal finance expert JL Collins discusses the concept of "FU" money, the importance of living on less than you earn, the power of l…
The Power of Trust and Skepticism with Jamil Zaki [not-audio_url] [/not-audio_url]

Duration: 52:20
#193: Unlock better opportunities, improve your emotional and physical health, and build stronger relationships by embracing “hopeful skepticism.” Dr. Jamil Zaki shares science-backed, actionable strategies to overcome t…
How I Saved Over $20K on a Luxury European Vacation [not-audio_url] [/not-audio_url]

Duration: 1:13:20
#192: Here's how we saved over $20,000 on our recent Europe trip! Learn how to use award flight tools to score affordable business-class tickets, maximize hotel loyalty programs for luxury stays, and find incredible trav…
11 Lessons Every Investor Needs to Know with Ben Carlson [not-audio_url] [/not-audio_url]

Duration: 55:15
#191: Grow your wealth and build a resilient portfolio by making smarter decisions with these 11 investing lessons. Financial advisor Ben Carlson and I share actionable insights on managing risk, overcoming psychological…
Why High-Performers Focus on Energy, Not Time with Sahil Bloom [not-audio_url] [/not-audio_url]

Duration: 48:51
#190: Transform your relationships, productivity, and overall quality of life by discovering how to be intentional with your time. Sahil and I share actionable tactics to build better habits (and get rid of bad ones), im…
My Must-Have Products and Services for Life, Work and More [not-audio_url] [/not-audio_url]

Duration: 59:29
#188: Here are the 130+ things I cannot (or don’t want to) live without, including my favorite tech, web and mobile apps, travel gear, subscriptions, banks and financial tools. I also share health and fitness items, smar…
42 Travel Planning Tips & Hacks from Travel Pro Leigh Rowan [not-audio_url] [/not-audio_url]

Duration: 1:09:15
#187: Learn the art of travel planning to enjoy incredible vacations. Travel pro Leigh and I share over 40 practical tips to create the perfect itinerary, save on flights and hotels, find travel inspiration, experience d…
25 Money Rules (and When to Break Them) with Brian Feroldi [not-audio_url] [/not-audio_url]

Duration: 55:22
#186: We'll break down 25 investing and finance rules of thumb, so you can learn to make better financial decisions, whether your goal is growing your wealth, retiring early, managing your portfolio, buying a car, or man…