All the Hacks: Money, Points & Life How to Actually Live the Life You're Optimizing For with Sahil Bloom
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Mar 25, 2026 
Sahil Bloom, writer, investor, and creator of The Curiosity Chronicle, gets into why over-optimizing life can erase what matters most. He talks big fast decisions, the doorman fallacy, family versus opportunity, and using AI as a thinking partner. They also dig into time blocking, systems over motivation, and building routines that actually support life.
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Schedule The Life You Moved To Create
- Structure the behavior you want after a big life change instead of assuming proximity alone will create it.
- Sahil Bloom says living near family increased random interactions, but dinners and one-on-one time still need calendar slots.
Leaving New York Improved The Relationships He Valued
- Sahil Bloom worried leaving New York would shrink his access to interesting people and events, but his calendar showed he already declined most invitations.
- He now visits once or twice a month for intentional one-on-one dinners and jam sessions, which fit him better than group events.
Use AI To Challenge Your Fear Based Decisions
- Write down your fears, then deliberately argue the optimistic case against each one to test whether they are real.
- Sahil Bloom did this before moving, then used AI to play devil's advocate and expose better outcomes he was overlooking.
