Adam's Perspective

I wanted to revamp WordPress Playground UI for a while but I couldn’t get any useful results from LLMs.

Until today. I’ve shared my struggle on Slack and Chris Huber inspired me to ask it not for 100 iterations on one design, but for 100 different designs.

So I did.

And I got 100 designs. It took Codex maybe 30 minutes. And then I asked Claude for 100 more and it did about 80 before it ran out of tokens on a Max x20 plan! I picked the ones I liked and asked codex for variations on them and got 50 more, then another 50, then another 50, then 40 more, and another 40.

None of them is ready, but I’ve explored a lot of possible directions and really liked a collapsible left bar as an alternative to the current interaction model. So I’ve asked Codex to riff on that. It created 10 more options that I didn’t really like so now I’m waiting for my Claude tokens to renew. Also, in the background, I have a team of codex agents figuring out a way to make codex produce better designs.

Until today, I’ve tried to use the model to recreate the design process I’m familiar with. That didn’t seem to work. Right now I’m discovering a new kind of process where more than 99% of the work is meant to be discarded. We’d never do that with people, but we can do that with LLMs.

I still don’t know if I’ll end up with any actually usable design. This is work in progress. Still, I’m very happy I got to scroll through 400+ design variations, have a visceral reaction to the ones that didn’t work, and get excited at the one that does seem to work!

My prompt

I’ve used a variation of this prompt multiple times today. I was inspired by Dan Luu’s and Dennis Snell’s work:

/goal use Chrome or something to that effect to get a series of screenshots of playground. wordpress.net, see the user flows involved in creating and managing and saving playgrounds go go deep into different models, map it out, and then create a new Tmux session where you will supervise 10 agents at a time

We want to create a 100 sessions in total. Each session will explore a different redesign redesign of the WordPress Playground UI. It must consider user flows. It must prioritize usability, making it easy to discover features to use them. It must preserve the end goals that the current UI enables the user to do, but it can expose them in a different way. It can remix parts of the UI, merge some of the screens, remove others, anything’s allowed as long as we don’t lose features and don’t add features that are not in there right now. Every session should create an HTML file or like a set of HTML files. CSS JavaScript is also fine. create a brand new repository on GitHub under adamziel. and you will be pushing all those designs there I also want to have a GitHub page where they will all be linked and I’ll be able to easily browse them.

You should also have an 11th session that is a critic that will provide feedback for all these design sessions, and it should have a very high quality bar. If any any cloud session dies, restart it, like if it dies prematurely. If it finishes the task then great, just stop it, make sure the work is pushed to the remote repository, clean up any local changes it might have done, and start a new session in its place, until our remote repository with HTML designs have a 100% total new high fidelity wireframes in it.

LLM design strategies I’ve tried before that didn’t work for me

Also known as all my prior strategies:

• Asking Codex/Claude Code to analyze the Playground UI, finding a better user journey, and producing a production-grade HTML design. It always produced unusable motley abominations.
• The same, but with frontend design skills. The abominations were now internally consistent. Still unusable, though.
• Claude design. It started promising, but it only got me about 60% there and nothing I did made it improve. Every iteration took substantial time, too, so I gave up.
• Figma AI and Figma MCP. That one took me about 70% there and iterated faster than Claude Design. I still couldn’t get any closer to ready.
• Giving it Chrome MCP, feeding it screenshots of designs I liked, very patiently stating what I want and handholding it through changes.
• More iterations, in any way: Ralph loops, adversarial loops, saying iterate on this 100 times, reflect and improve, work in a loop until it’s 6pm, etc.