Write with whimsy — play, not judgment

Early AI — around GPT-2 — could genuinely surprise you. Feed it "in the shower, he was…" and it might answer "eating a lemon and thinking about his ex-wife": useless to paste into a newsletter, but it could fling your imagination somewhere you'd never have gone. That unpredictability has since been smoothed away, leaving a parrot that returns the most middle-of-the-road answer every time. The human thing it's losing is whimsy — the willingness to follow a thread into the unknown just to see where it goes.

How it works

Whimsy isn't a trait so much as a stance toward the page. The philosopher Martha Nussbaum reportedly treated her typewriter as what psychoanalysis calls a transitional object — not an instrument of anxiety but a toy, a security blanket, a thing safe enough to lose herself in. That reframe changes everything. If writing is a medium of judgment — you put ideas out and people evaluate them, and you — you'll approach it braced and anxious. If it's a place of play — an extension of your thinking, a way to pull on the ribbon of your own curiosity — you stop performing and start discovering. You follow a thread not because it leads somewhere you pre-planned, but because it's interesting, and you let the writing surprise you.

Why it matters

Creative unpredictability comes from exactly where the other human skills come from: being alive, having a body, having something at stake, playing. AI has been optimised to produce the expected, the safe, the averaged, so it can't wander — and wandering is where the surprising, the alive, the un-generatable lines come from. Play is also what makes writing bearable: the same page feels like a threat under judgment and a toy under curiosity.

Freewriting: generate, then sculpt

The practical form of play is freewriting, and its one rule is to keep two stages apart. Stage one, the drop: pull a little of the unconscious to the surface each day and let it hit the page, where it cools into whatever shape it takes — you don't get to decide, and you can't call it good or bad, because it isn't for anyone yet, including you. Stage two, the sculpting: hours or days later, the analytical mind comes online, reads what surfaced, and shapes the few live bits into something useful or beautiful. The order is everything — you cannot sculpt magma, and you cannot generate while you judge, because judgment scares the material back underground. Expect ninety percent to be trash; the ten percent that isn't is better than anything you could have planned.

Try it

1. Reframe the session: not "I must finish this," but "let's see where this goes."
2. Follow one thread purely because it interests you, with no pre-planned destination, and let it surprise you.
3. Find your transitional object — a notebook, a pen, a ritual — that makes the page feel safe enough to play in.

Common pitfalls

Mistaking play for no standards. Whimsy is how you generate; you still revise with judgment later — they're different modes, not the same one. The opposite failure is treating every draft as a final verdict on your worth, which is the surest way to write nothing but the safe, expected, average thing a machine already writes.

If you think of writing as a place of play, an extension of your thinking, then you stop performing and you start discovering.

WILLIAM · THE 5 WRITING SKILLS AI WILL NEVER REPLACE · 2026

AI is optimised for the expected. Whimsy is the willingness to follow a thread into the unknown.

Drawn from

• William, The 5 Writing Skills A.I. Will Never Replace (Writer Science, 2026).
• William, This Video Will Find You When You Want to Give Up Writing (Writer Science, 2026) — freewriting, and separating the drop from the sculpting.
• Related: When you're blocked, stop forcing it, Trust the night shift, Write to think, not to report, Voice is lived experience, not word choice, Out-human the machine.