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Sahil’s Monthly Idea Drop: July 2025


Episode 350


If you read (or listen) to this newsletter, you know that I’m obsessed with interesting ideas.


Here are 5 ideas I can’t stop thinking about this month…


(P.S. This may become a regular monthly segment i…


Published on 3 months ago

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The Cheshire Cat Principle: How to Create Clarity


Episode 349


In Alice’s Adventures in Wonderland, there’s a scene in which Alice reaches a fork in the road and has a simple exchange with the Cheshire Cat:

“Would you tell me, please, which way I ought to go from…


Published on 3 months ago

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The Empty Boat Mindset


Episode 348


There’s a story I come back to when I’m feeling stressed or frustrated...


A monk is meditating alone on a lake when another boat crashes into his. Anger rises—until he opens his eyes and realizes the …


Published on 3 months, 1 week ago

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The Arrival Fallacy: Why Success Is Never Enough


Episode 347


Last week, the world's top-ranked golfer, Scottie Scheffler, went viral for something completely unrelated to golf.

During his pre-tournament interview at The Open Championship, one of four annual maj…


Published on 3 months, 1 week ago

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The Poem I Wish I Read 10 Years Ago


Episode 346


Last week, a reader sent me a poem that stopped me in my tracks.

To live content with small means.
To seek elegance rather than luxury,
and refinement rather than fashion.
To be worthy not respectable,
an…


Published on 3 months, 1 week ago

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The Poison Arrow Principle: How to Stop Overthinking


Episode 345


Here's an old Buddhist story I think about often:

Imagine someone is struck by a poisoned arrow. A doctor is called to remove the arrow, but the man stops him. 'Not so fast! Before you remove it, I wa…


Published on 3 months, 2 weeks ago

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22 Pieces of Career Advice They Don't Teach You in School


Episode 344


I get a lot of messages asking for career advice.


The following is my attempt to synthesize my responses from the last few years into a series of short, valuable lessons.


Behind each of these is a much…


Published on 3 months, 2 weeks ago

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The Question That Haunts High Achievers


Episode 343


Last week, I was speaking to a group of entrepreneurs when one of them admitted he'd been struggling.


He's dealing with a challenging family health situation and feeling like he isn't doing enough to …


Published on 3 months, 2 weeks ago

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The Artful Life: Ars Longa, Vita Brevis


Episode 342


In the 4th century B.C., the Ancient Greek physician Hippocrates, wrote in his Aphorisms (translated into Latin here):

Vita brevis, ars longa, occasio praeceps, experimentum periculosum, iudicium diff…


Published on 3 months, 3 weeks ago

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The Jonah Complex: How to Stop Running From Your Own Light


Episode 341


On a windy pier in the ancient city of Joppa, a young man buys a one-way ticket to sail in the opposite direction of his destiny...


The young man, Jonah, had been called upon by God to travel to the c…


Published on 3 months, 3 weeks ago





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