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The Roundup: How to defeat jargon, win over a pushy PM, and fix the collaboration gap
What we learned from Blain Billingsley, staff designer at OpenAI
1950s Designers Using Type as Art: The Creativity Behind the Jazz Covers of Prestige Records

When Designers Collaborate
A designer chalked the album's lineup on the side of a railroad boxcar. He wasn't a photographer yet, so another designer took the shot. Your best work might need a skill you…
The Limits Are What Make the Project
So much is at your fingertips now. That's the problem. The constraint you're fighting often sets your work apart. Every Prestige Records designer asked the same question: what can…
Blaine Billingsley: OpenAI designer on the collaboration problem AI hasn't solved yet
Episode 192 of the Design Better Podcast
The Type Was the Art
Your type probably goes on last. One self-taught designer stayed up until two or three in the morning with type foundry catalogs, figuring out how it was done. Choose, color, and…
The Brief: 7 Principles for better AI collaboration
Principles and a downloadable kit for anyone who wants to work more efficiently with AI collaborators.
How Freelance Designers Off the Street Made Some of the Best Album Covers of All Time

Mack Paul: Co-author of Miracle Road on designing places where innovation happens
Episode 191 of the Design Better Podcast
The Roundup: Why some of Google's best designers spent time as PMs
Google let designer Niyati Gupta try being a PM and she became a better designer for it.
Technology Is Rude
Every polite thing you do for a stranger, you do without a word. Your product reads none of those cues, so it interrupts at the worst moment. The fix is not a smarter device…
Why Humane and Rabbit Didn't Work
Putting an LLM in a box does not put AI in the physical world. Alexa failed the same way. A device that cannot see what you are looking at or which room you are in will never read…
Why You Never Find Out What a New Technology Could Have Done | Leonardo Giusti, Ex-Google ATAP

Federico Casalegno: Samsung EVP on how 20,000 years of creativity shapes design today
Episode 190 of the Design Better Podcast
AI Isn't a Thinking Machine, It's a Thinking-With Machine
Delegation is not a fact about AI. It is a metaphor you inherited. Swap it for augmentation and the work changes shape. AI you think with sharpens your decisions and shows you…
Why 'Let AI Do the Work' Is the Trap Every Designer Falls Into | Leonardo Giusti, Ex-Google ATAP

Every Icon Drawn by Hand
A 16 by 16 grid is the one thing AI still cannot draw. Yoto tried every model. They all make beautiful full resolution images, and none can make good pixel art. Constrain the…
How Lack of Experience Helped This Design
Expertise would have talked them into something more complicated. Yoto had never built hardware, so they built the obvious thing instead: children love putting things into things…
The Roundup: Staff product designer on getting used to change
A special sponsored version of The Roundup in partnership with Rosenfeld Media
Don't Call It a Toy
Slapping an animal face on an adult device is the lazy version. Build for children from the ground up, then ask one question: at a dinner party, would the adults hide this, or…
The Design Decisions That Stop a Child Outgrowing It | Ben Drury, Yoto Co-Creator

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Jonathan Adler returns: The minimalist inside the maximalist
Episode 189 of the Design Better Podcast
Designing for Children When Screens Are Everywhere | Ben Drury, Co-Creator of Yoto
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