Essays

Chapter 58: From India, with Love.

A week in India for Tanmaye's wedding. Highlights include sick outfits, Delhi Belly, five days of fun.

Dec 26, 2025 • Jack Raines

Some thoughts on "Head of Narrative"

The hottest new job in Silicon Valley.

Dec 18, 2025 • Jack Raines

What Are You Optimizing For?

On separating the means from the ends and avoiding the inertia trap.

Aug 22, 2025 • Jack Raines

Okay, I wrote a book.

Is this thing on?

Jul 17, 2025

Another trip around the sun. Some thoughts on saying goodbye to my mid-20s, going monk mode for a few months, etc.

Apr 7, 2025 • Jack Raines

Investing in Creators.

The creator economy is dead, long live creators.

Feb 17, 2025 • Jack Raines

The Late-20-Something's Professional Dilemma

On the pressure to figure out your "thing".

Jan 23, 2025 • Jack Raines

A new appreciation for South Georgia, a few other thoughts.

Dec 6, 2024 • Jack Raines

You Only Have to Get Rich Once.

Hitting it big in the market is electrifying, but can you hold on to what you made?

Nov 21, 2024 • Jack Raines

Some Thoughts on What Makes New York so Great.

I have, surprisingly, become New York City's biggest apologist.

Oct 17, 2024 • Jack Raines

Status Games Rule Everything Around Me.

Everyone's chasing something.

Oct 3, 2024 • Jack Raines

The Cost of Apathy.

Modern life has a modern problem: we don't have to do anything.

Aug 6, 2024 • Jack Raines

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