AI x Creativity

Si Cobb

05 Sep 2026 — 1 min read

In planning and design theory, a 'wicked problem' is

a problem with no definitive formulation, no clear stopping rule and no objectively correct solution

Most math problems would be the opposite of a 'wicked problem'. You see the question, the stopping rule is arriving at the answer which can then objectively be deemed correct (or not if you're 16 year old me).

Computers (and AI) love a 'tame' problem where the formuation, the stopping rule and the correct solution are clear.

Any creative act: writing, sculpture, performance, painting, poetry is a 'wicked problem'.

'I want to make something cool and interesting' is not a definitive formulation.

Anyone who's ever made anything knows that knowing when to stop and leave it alone is really hard. Creativity has no clear stopping rule.

And there's no objectively correct solution. Humans are amazing at creating diverse artefacts in the name of art. How are we marking these as correct or not? We can't.

So much depends on taste, style, connections, feelings.

And that's why I don't think AI is a threat to creative trades until it can crack this.

AI has no unique point of view rooted in its individual taste, style, connections, and feelings.

So, go post that article, draw a picture, make your music, perform your comedy. Nobody wants the AI slop version.

Create a wicked problem. Other humans will love you for it.

Cartoon self-portrait with a thought bubble containing a 'No AI' sign.

I don’t use AI for any creative now

I don’t use AI for any creative endeavour any more. I’m not a hater, it just doesn’t work for me in that space these days. YMMV. However, it is perfect for work. The AI’s distillation of the Internet into a smooth, even, flavourless slop maps exactly

A red clown nose that has been thrown into a bin

So I Quit Clown Class

I always wanted to do physical comedy. I took a clown class to push my body to explore its capacity and capability for comedy. Instead, it pushed me into a space where I don’t fit. A box so uncomfortable that its fiendish design opened my psyche up like it

Portrait photo of the author. Si is smiling, with his arms crossed. He's wearing a black t-shirt.

What 50-Something Looks Like

So this is what being 50something looks like. But I only know that from looking in a mirror. When I go out, I do not know what 50something looks like. I don't much go to the pub, alcohol takes more than it gives. I look after myself, I

three cyborg figures, 2 female, one male. They have badass robotic enhancements to their flesh and blood bodies.

Everyone's a Maker Now

Everyone’s a maker now. Everyone’s a maker, everyone’s a project manager. If you’ve ever worked in an engineering team then you might recognise this trope: engineers only respect other engineers. Everyone else is just in the way of them writing their beautiful code. Designers add unnecessary

Read more

I don’t use AI for any creative now

So I Quit Clown Class

What 50-Something Looks Like

Everyone's a Maker Now