ChatGPT Images 2.0. DESIGN.md. The First AI Casualty.
Field Notes from the In-Between
Kris Puckett, Design Manager at Stripe, spent months building Epilogue, a real iOS app with 14,000 lines of Swift, entirely through conversation with Claude. This essay is a specific and honest account of what the designer-building-with-AI experience actually looks like: what broke, what he learned about asking precise questions, what “vague frustration keeps you stuck, specific confusion gets you answers” actually looks like in practice. “I realized the bottleneck was never coding ability. It was articulation. The ability to describe what I wanted clearly enough that something else could build it.”
Some Notes on AI
Karri Saarinen, CEO of Linear, writes one of the more grounded takes on AI’s current state. Linear’s cloud agent now fixes more than 1,000 issues per month, but Karri is clear that hard problems remain hard and design tools are still challenging to use. On having a design tool operate directly on the production codebase: “A lot of the design work I do is not production design. I am not trying to implement the final version or test every edge case. Most design work is about making decisions, understanding the problem, and finding the fit. That process generates many variations and messy ideas.”
The expertise paradox section is the most useful: “AI often feels most impressive in domains where you know the least.” Expertise makes AI harder to use but also more valuable, because experts know how to steer, constrain, and evaluate the output.
What’s worth making?
“Designers have always (and will always) answer the question ‘What’s worth making?’ ” Joel Lewenstein, Head of Design at Anthropic, argues that as the cost of software drops, the most important decisions shift from “can we make this?” to “should we?” Design, in his framing, is what narrows the possibility space fast enough to keep up with the speed of delivery. He describes Claude Design as a tool for getting ideas “good enough to move discussion forward,” cutting idea-to-internal-feedback time from days to hours.