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Roger Wong - Design, UX, AI, Technology

The design blog that connects the dots others miss. Thoughts on design systems, user experience, artificial intelligence, and technology.

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Agent Experience Needs Failure Affordances

Organizations often miss work their metrics were not built to see. AI agents face a similar problem when they encounter something their rules cannot handle. Service designer and University of Michigan urban-technology professor Ron Bronson turns to Stafford Beer’s idea of algedonic signaling: a way ...

Design work isn’t vague. Our measurement is.

Service designer Daniel T Santos uses British cybernetician Stafford Beer’s Viable System Model to explain why strategic design work can disappear in plain sight: System 1 is operations: these are the units that produce the countable output. The screen ships, the order moves, the revenue lands. Syst...

A design language is more than a visual theme

Jem Gold's encounter-language—describing how a design should feel rather than what it is made of—puts the intended experience into words. Design systems leader Yesenia Perez-Cruz, who led Shopify’s Polaris system, takes the next step: giving a team enough shared structure to express product mean...

Design Is How It Tastes

Have you ever walked into a fast food restaurant lit with overhead fluorescent lights and knew immediately that it might be a bad idea? Or if you walk into a slightly more upscale eatery with warm, incandescent light and it immediately feels inviting? Creative technologist Jem Gold illustrates a sim...

Can you actually grow old as a creative, successfully?

Ageism in design is real. In my last job search a couple of years ago, I got zero callbacks. I landed a new role via connections. What's kept me sane and relevant has been curiosity. Tom May, writing in Creative Bloom: One thing does need to stay sharp, though. As creative director Olivia Downin...

Why Is Everyone In Tech So Sad?

On a morning train, Aaron Horwath, writing in Noema about AI and knowledge work, watched a fellow commuter spend over half an hour talking through financial metrics, including margins and cost structures. Then the man pulled a pair of knitting needles from his bag. He was making a pink winter hat fo...

Bottle your judgment and make it outlive you

Dan Maccarone, product strategist and co-founder of the design studio Charming Robot, draws a line between what expertise can be documented and what must still be learned through first-hand experience: The move nobody makes: run both plays on purpose. Structure what you can, and still teach it to a ...

The Bull And Bear Case For Digital Design In The Age Of AI

Andy Budd, Clearleft co-founder and longtime design leader, argues that AI may make design organizations smaller while making some design roles larger. His bull case is that designers who can move across product, craft, commerce, and implementation gain agency instead of getting stuck in production ...

How to Run a Gauntlet Loop

Matt Shumer, writer of the viral "Something Big Is Happening" essay, argues that most agent workflows try to prevent mistakes by specifying every move. His Gauntlet Loop takes a different approach: define what good looks like, then let the agents decide how to reach it. You give a lead age...

What Star Trek got right about AI

I'm am a pretty big Star Trek fan. As any good GenXer, I grew up with Star Wars, but I loved and still love the Star Trek universe. It just tickles the nerdier side of my brain. I love this essay by Patrick Neeman exploring how Star Trek correctly predicted aspects of modern AI. Neeman: Star Tre...

AI Isn't Killing SaaS. SaaS Is Killing Itself.

In Jason Lemkin’s account of SaaStr’s break with Adobe Marketo, the formal cancellation is almost beside the point. SaaStr had already moved most of Marketo’s work elsewhere: And once you do that once, you start asking the obvious question. We’ve now migrated almost all of Marketo’s functionality on...

'Almost everyone is having an existential crisis': Designers share how they're surviving an industry in constant flux

Judgment and craft may help a designer survive today’s freelance market. But Madeleine Morley, writing for Fast Company, gives us little reason to believe that either would guarantee economic security. She interviewed Cari Sekendur, founder of the independent branding and web-design studio Butter. I...

Training design senses

Creativity researcher Keith Sawyer described art and design school as a place where students learn to see their own work: they bring unfinished work into critique, hear what others see in it, and practice identifying the gap between intention and result. David Hoang turns that studio lesson into exe...

Sculpting a shapeless medium

Intent is one of my go-to coding workspaces. By default, it's spec-driven and uses swarms of agents to execute the work, with a brainy orchestrator agent coordinating it all. Ryan Mather, interviewing the product lead for Intent, designer-developer Amelia Wattenberger for AI Design Field Guide, ...

Product Quality: A Shared Commitment to Craft in the wake of AI

The startup grind is often the same: ship fast, but maintain a high bar of quality. At least that's the sentiment. Those things are in opposition and the system incentivizes people to just move on. Miguel Fernandez, writing for Slack Design, describes why shared standards matter: Craft is subjec...

Charlie Deets - Designing the internet computer

At Apple, my boss Hiroki Asai, then the VP of Graphic Design, often gave me the same feedback: “This needs to be more considered.” Meaning, spend more time with it. Keep your quality bar high. That memory came back while listening to Michael Riddering interview Charlie Deets, a former Safari designe...

Robert Beatty on retro Photoshop, creative friction and designing album covers that feel almost primeval

Album-cover and gig-poster artists capture the feeling of music while building a visual identity around it. I respect anyone who can pull off both. Paul Moore, writing for It’s Nice That, talks with artist and album-cover designer Robert Beatty about old versions of Photoshop, scavenged technology, ...

The Dark Arts of Skill Engineering

Paul Bakaus says he helped turn Impeccable from what he calls a “vibed personal skill” into a design toolkit. He says hundreds of thousands of designers and developers now use it. Three of his techniques show how much of that improvement came from engineering around model behavior instead of polishi...

The new rules of context engineering for Claude 5 generation models

If you're configuring agents for product and design work, start by cleaning up their context. Anthropic's Thariq Shihipar offers several recommendations; three are especially useful here: First, replace blanket prohibitions with an instruction that lets the model read the code around it: In ...

Software development is dead

Product designer and UX Planet editor-in-chief Nick Babich describes software development shifting from production to direction. The design version is familiar by now: as interface production gets cheaper, the work beyond the artifact is defining the right problem, directing agents, evaluating outpu...