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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October 2025

The Personal Assistant in Your Pocket: What It Takes

Apple's Siri promised us a personal assistant in our pockets 15 years ago. Now in the age of agentic AI, that promise could finally come true, but only…

Oct 28, 2025 • Anna Barber, Céline Vendler, and Artificial Whimsy

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Is it an art-house short or a B2B SaaS ad?

Every AI launch looks like an A24 trailer, and Silicon Valley has decided its next competitive edge is taste. We set out to answer what taste really…

Oct 8, 2025 • Artificial Whimsy

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