What I Learned from Two Years of DisOrientation

A last lecture on having the courage to ask who you're writing your story for, and rewriting it, even if it feels too late

Jun 21 • Artificial Whimsy

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May 2026

Who's a better writer: AI or me? Part 2

The NYT says people can't tell AI from human writing. We disagree. A close reading that will ruin AI writing for you forever.

May 13 • Artificial Whimsy

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April 2026

Dropping Out and Other Low-Risk Life Decisions

Risk has never been cheaper, yet commitment has never been harder. On the Thiel Fellowship, the dizziness of freedom, and Silicon Valley accidentally…

Apr 29 • Artificial Whimsy

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Who's a better writer: AI or me?

We took the NYT's viral AI writing quiz and (surprise!) have many, many thoughts

Apr 8 • Artificial Whimsy

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March 2026

The Permanent Underclass Has Good GMAT Scores

On credentials, Claude Code, and going swimming anyway

Mar 11 • Artificial Whimsy

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February 2026

We are once again asking...to know who you are

A favor to ask and a gift to offer :)

Feb 25 • Artificial Whimsy

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It be like WHAT sometimes

On the limits of meme-speak and why we don't just say what we really mean

Feb 4 • Artificial Whimsy

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January 2026

Good Grief

Lessons on loss from a play about memory and a real goodbye

Jan 15 • Artificial Whimsy

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December 2025

2026 currents and countercurrents

What will you swim towards in the new year?

Dec 31, 2025 • Artificial Whimsy

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A Last-Minute Gift Guide for People Who (Mostly) Don’t Need More Stuff

December is a strange time of year.

Dec 18, 2025 • Artificial Whimsy

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The little voice of your desire

Lessons from literature & life on how to listen for it in the noise of external pressures. What do you really want?

Dec 3, 2025 • Artificial Whimsy

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November 2025

What Could Happiness Cost—$10 Million?

How Silicon Valley's wealth culture distorts our definition of "enough," and how ambition might regain its imagination.

Nov 19, 2025 • Artificial Whimsy

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