Subscribe
Sign in
Home
Advice Column
Business & Culture
Dear Diary
About
Dear Diary
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
41
2
1
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
1,602
89
265
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
31
8
1
Good Grief
Lessons on loss from a play about memory and a real goodbye
Jan 15
•
Artificial Whimsy
17
2026 currents and countercurrents
What will you swim towards in the new year?
Dec 31, 2025
•
Artificial Whimsy
34
4
3
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
33
2
6
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
267
26
24
An elegy for now
AI distorts our conception of time & space. Everything is totalized yet summarized, immediately available yet degrees removed. Look up, look around—the…
Jul 23, 2025
•
Artificial Whimsy
6
3
1
Art, artifice, and the artificial
Can AI make something truly beautiful? The bar for makers is higher now. To risk not making a Mission Impossible 7 Pt. 2, but to risk being disliked. To…
Jul 9, 2025
•
Artificial Whimsy
8
1
Memorial Day 2025
Some long weekend thoughts...belonging is older than language. As our tools get smarter and teams smaller, the question isn’t what we can build…
Jun 4, 2025
•
Artificial Whimsy
5
1
1
Not Ideas About the Thing But the Thing Itself
Love has always been shaped by risk, friction, and loss. As AI learns to mirror us more convincingly, the greatest loss may not be work or truth, but…
Apr 30, 2025
•
Artificial Whimsy
8
1
1
This site requires JavaScript to run correctly. Please
turn on JavaScript
or unblock scripts
