Happy 50th Birthday, Apple

The first time I wrote about Jenny Wen, I pushed back. She said the design process was dead, and I argued the proportions had shifted but the process itself was intact. I also noted a context problem: her “ship fast, iterate publicly” approach makes sense for greenfield AI products at Anthropic but gets harder with established install bases.

Wen has been making the rounds and in a new interview, I’m finding a lot that I’m nodding my head to.

Jenny Wen, speaking on Tommy Geoco’s State of Play:

Often design needs to follow what the model is capable of and design from there, as opposed to starting from a design vision first. I think that can feel tough as a designer because you’re like, oh, I want to be design-led, we should be designing it first and then the technology should follow. But I think that’s just the reality of working at a research lab where the technology is emergent and you have to sort of decide what to do with it.

“Design follows the model” is an interesting phrase from a design leader. It inverts the dogma that design should lead and engineering should follow. But Wen isn’t being defeatist. She’s describing a practical reality at at a leading AI lab where the models’ capabilities are changing faster than any roadmap can account for.

This shows up concretely in how her team works:

The big thing is designers are implementing code, through using Claude Code. That has been the biggest difference from working at Anthropic versus back when I worked at Figma. […] Even today, we were reporting some bugs and some quality issues, and one of the designers was like, “Cool, let me just fix them.” And that was cool to just not have to tag an engineer for them to do anything.

A designer casually fixing production bugs without tagging an engineer. Just another Tuesday at Anthropic.

Geoco’s summary of Wen’s argument crystallizes something we’ve all been thinking quietly about:

She said, having taste versus being able to execute are two completely different things. They’re usually bundled together, but they don’t have to be. And in a world where AI can increasingly execute, the question becomes, and it’s kind of uncomfortable, do you actually have good taste or are you just pushing pixels around?

That’s the thread tying all of this together. When designers are closer to the product, fixing bugs in production, prototyping against the live model, the judgment they’re applying isn’t visual. It’s product sense: knowing which of those 12 options is worth shipping, which edge case will break trust, when the model’s output is good enough for real users. That’s the taste Wen is describing, and it has very little to do with pixels.

A lot of designers have been coasting on execution skills that felt like taste. They debate corner radii and centering labels in a button with amateur vs pro designer memes. Who cares! AI is about to make the difference visible.

I used Claude to author a process document for my team. After a lot of back and forth, it produced a thorough 4,000-word doc. And then I spent the next 30 minutes reading it, line by line, making sure every recommendation matched my intention.

The AI produced the document in minutes. I evaluated it at human reading and review speed.

Jakob Nielsen has a name for this bottleneck: evaluability. He argues it should replace execution efficiency as the central UX metric:

In command-based UIs, the user’s primary cognitive load was executing the task step-by-step. In intent-based systems, execution is cheap, but evaluation becomes the bottleneck. The usability metric shifts to how rapidly and accurately a user can verify that the AI’s output matches their actual goal. Interfaces must be optimized for “evaluability,” allowing users to judge quality and appropriateness without painstakingly combing through every detail of the result.

“Without painstakingly combing through every detail” is exactly what I was doing with my 4,000-word document. We don’t have the interfaces for this yet. We’re still reading AI output the way we’d read something a colleague wrote, except a colleague wouldn’t hand me 4,000 words and say “check this.” (Unless of course, they wrote it with AI and then, of course they would.)

In agentic engineering, you often hear that code review is the bottleneck.

Nielsen again:

Our designs must not act as cognitive wheelchairs that replace human agency; they must act as cognitive exoskeletons that support and enhance human flourishing, even as traditional work vanishes. Good AI UX will teach just enough, reveal plan structures, and leave a comprehensible trail of action so users can maintain digital judgment.

Most AI interfaces are optimized for generation speed. The harder problem is on the other end: helping humans evaluate what got generated. Until we solve that, productivity gains from AI come with an evaluation tax paid at human speed.

Most AI tools start with a blank chatbox. OK, maybe not completely blank. Often there is a gallery of examples right below the input. But it’s still hard to come up with something original when faced with a blinking cursor.

Brad Frost calls this moment “the Creative Infinite”:

Never before in human history has it been possible for anyone to simply ask for something to exist, and then it just…exists. Where the inputs can be anything, the outputs can be anything, and the whole process can be repeated, iterated, combined, translated, and chained together indefinitely.

He makes the case concrete with his 8-year-old daughter:

In 5 minutes, Ella vibe-coded a playable game (built in Three.js via Claude Cowork) running in the browser. That’s just bonkers. At no point in human history has it been possible to simply describe a game in words and then just… play it 5 minutes later.

A Michael McDonald (interesting taste for an 8 year-old!) penguin adventure, because she knew it would make her dad laugh. The capability is real and the story is delightful. But then Frost hedges:

Your existing creative fluency still matters, maybe even more than before? Just as being able to play piano puts you in a better spot to wield a synthesizer. Knowing how to design makes you better at prompting visual tools. Understanding code makes you better at architecting what you want to build with AI. Craft. Taste. Art. Authentic expression. Purpose.

Yes, creative fluency matters more. It absolutely does. The piano-to-synthesizer analogy is exactly right: the tool revolutions I’ve lived through have compounded on existing skill, not replaced it. A designer who understands visual hierarchy and restraint will direct AI better than someone who’s never thought about why one layout works and another doesn’t.

When I was a younger designer, I always started with a pen and sketchbook. Sketch first, think with your hands. Now I write first to understand the problem space, then sketch. The images come after the words.

Elizabeth Goodspeed, speaking on Nicola Hamilton’s DesignThinkers podcast, takes this further than I ever would—she can barely picture images at all:

I am far more towards aphantasia. I have a very limited view of things in my mind. I think the analogy I use is it’s looking at an apple in a dark room and the lights are turning on and off and I’m wearing sunglasses and also the apple’s moving.

Her ideas don’t start as images. They start as words:

My ideas are usually very conceptual verbal, not even sentences. I guess I’m a robot—I don’t have an inner voice either. It’s just a pure void concept up there.

That might explain why Goodspeed is one of the sharpest design writers working. When you can’t conjure images internally, language becomes your primary tool for developing ideas. The archives and ephemera she’s known for aren’t aesthetic mood boards—they’re external memory for a mind that processes concepts before forms.

Goodspeed on the myth of the visually inspired designer:

That to me is damaging to creatives because it has this idea that we’re this noble savage where these images just move through us and we see everything in this Willy Wonka kind of way. In reality, I think it’s a process just like any other making process, whether that’s a carpenter or writer or anything else. It actually, I think at its best, is methodical and not just this inspired bolt of lightning.

The best design work starts with a concept, not a visual. Goodspeed just happens to have a neurological reason for working that way. The rest of us had to learn it. Worth listening to the full conversation—she also covers teaching, thesis panic, and why she calls her own work “graphic design fan art.”

Stripe design manager Kris Puckett, speaking on Michael Riddering’s Dive Club, spent the first half of the conversation demoing metal shaders, custom ocean animations, and a full iOS reading app he built with Claude Code. Then he stopped himself:

AI native has to be beyond just “I made a really cool shader” or “I made this dither effect that every other person is making.” I was doing that today and then I was like, “Oh my gosh, this is… why am I doing this? There’s a hundred of these that are way better than what I’m making right now.”

So what does AI-native design actually look like? Puckett’s answer is “soul”—the quality that makes work feel specifically, unmistakably yours:

I think what people are going to be desperate for is more of that human side of things. They’re going to be longing for […] an era they’ve never experienced because they’re younger, that MySpace generation where your MySpace page was deeply personal to you. My MySpace page was complete custom Kris Puckett perfection at that time. And I think that we’re going to want to see that come back. And I think people are going to want more of those—your portfolio looks and feels like you.

“Soul” is doing a lot of work as a concept there. What Puckett is describing sounds a lot like taste—the ability to make something that feels intentional and specific rather than procedurally generated. His workflow backs that up. Being contrarian, he explicitly rejects the “let the agent run” approach:

I want off that cycle. I do not want to be riding that bike race with anyone else because that’s not how I view these things. They are a force multiplier, but I want them to be focused. I want it to be something that I feel is still authentically me.

What unlocked all of this for Puckett wasn’t technical skill—he’s a designer, not an engineer. It was admitting “I don’t know” and starting anyway. He’d been dreaming of building his own software for 20 years. Claude Code’s blinking cursor was enough to get him started.

Figma is opening its canvas as a writeable surface for AI agents. Matt Colyer, product director at Figma, on why this matters:

Design decisions—from color palettes and button padding, to typography and interactivity—have always defined how products take shape. No matter how small, those decisions add up. They make your product and user experience stand out from the rest. To date, AI agents haven’t had this context, which is why so many designs created by AI often feel unfamiliar and generic.

The fix is beefing up skills files, by encoding a team’s design decisions, conventions, and sequencing rules. Agents read them before they touch the canvas. The use_figma tool lets Claude Code, Codex, and other MCP clients create and update assets tied to your design system. Colyer on what that changes:

Your conventions are no longer static documentation. They become rules agents follow as they work—applied through components, variables, and the structure you’ve already defined.

The detail worth paying attention to is what Colyer describes as a self-healing loop. When an agent generates a screen, it screenshots the result, checks it against the design system, and iterates. Because it’s working with real components and auto layout, those corrections compound through the system itself, not just the pixels on screen.

It’s free during beta, with plans to move to a paid API. Figma is finally joining the party as Subframe, Paper, and Pencil all offer this workflow already.

Shubham Bose loaded a single New York Times article page and measured what happened:

With this page load, you would be leaping ahead of the size of Windows 95 (28 floppy disks). The OS that ran the world fits perfectly inside a single modern page load. […] I essentially downloaded an entire album’s worth of data just to read a few paragraphs of text.

The total: 422 network requests, 49MB of data. Ouch! Before the headline finishes loading, the browser is running a programmatic ad auction in the background on his computer. Bose found the Times named its consent endpoint purr. “A cat purring while it rifles through your pockets.”

Bose on the economics driving this:

Publishers aren’t evil but they are desperate. Caught in this programmatic ad-tech death spiral, they are trading long-term reader retention for short-term CPM pennies. […] The longer you’re trapped on the page, the higher the CPM the publisher can charge. Your frustration is the product.

The UX consequences are predictable. Bose tears down what a reader actually encounters: cookie banners eating the bottom 30% of the screen, a newsletter modal on first scroll, a browser notification prompt firing simultaneously. He calls it “Z-Index Warfare.” On The Guardian, actual content occupies 11% of the viewport. On the Economic Times, users face two simultaneous Google sign-in modals before reading a single sentence. Close buttons are deliberately undersized with tiny hit targets. Sticky video players detach and follow you down the page with a microscopic X.

And on how no one person decided to make it this way:

No individual engineer at the Times decided to make reading miserable. This architecture emerged from a thousand small incentive decisions, each locally rational yet collectively catastrophic.

text.npr.org is proof that a different path exists.

Gui Seiz designs at Figma. His team uses Claude Code to bridge design and code. And he still reaches for the canvas when precision matters.

Seiz, speaking on Claire Vo’s How I AI podcast:

I don’t think we’re there yet in general with these code tools in terms of the precision editing that you want to do. […] I think still the gold standard for me is just being able to drag stuff around. And you can do a lot with a click that would take you a hundred words to write and to really precisely nail. No one wants to prompt for the exact hex code or the shade of yellow and that kind of stuff. That’s just easier to just quickly do and directly manipulate.

Seiz isn’t anti-AI. His team pulls production code into Figma via MCP, edits it visually, and pushes it back to the codebase. He’s bullish on what that does to the old workflow:

It’s definitely changed our workflows in a way that it’s really blown up what a workflow even is. Before, for the majority of our careers, we’ve had a very linear, agreed-upon workflow where you increase fidelity as you go on. Because it’s really expensive to work in code, and it’s really cheap just to trade ideas and sketch them out. But AI basically collapsed that, and it’s just as cheap to riff in code as it is to riff in design.

The cost of exploration collapsed. The need for direct manipulation didn’t. Both can be true.

I published an article about the design talent crisis in Fast Company! The setup is what I’ve covered before on this blog extensively. But there’s a connection that I draw with the trades—the construction industry and how they have a solution that the design industry could learn from.

In the article, I write:

Construction has been running formal apprenticeship programs since the National Apprenticeship Act of 1937, and informally for centuries before that. The Department of Labor’s Registered Apprenticeship Programs enrolled roughly 940,000 people nationwide in fiscal year 2024. These aren’t casual internships. They’re structured, multi-year pathways that pair inexperienced workers with seasoned professionals and build skills through graduated responsibility. The retention numbers tell you everything: Apprenticeship programs report a 93% employee retention rate. For every $100 employers invest, they see an estimated $144 return.

The contractors I work with don’t debate whether to invest in their pipeline during a downturn. They know that if they stop training apprentices, they won’t have journeymen in four years, and they won’t have master tradespeople in 10. The pipeline is the business.

There’s a three-point plan to dig us out of this hole. But of course, it requires committments from design leaders and the C-suite:

1. Stop tying junior hiring to project demand
2. Formalize mentorship
3. Accept the short-term cost

There is more to the article. Please take a read and share!

Sarah Gibbons and Huei-Hsin Wang, writing for Nielsen Norman Group:

What looks like “skipping the process” is just compressing it — running faster through the stages and using experience as a guide. […] What gets called “intuition” is really process, compressed and internalized through years of doing the work. The intuition designers trust was built by the very process they dismiss.

Gibbons and Wang on what comes after you stop pretending you’re not using one:

The real skill in modern design is not the ability to abandon process — it’s process literacy: picking the right approach and tool for the problem. Know which process fits the job and understand the risks of not following it. Better yet, don’t claim you’re not using a process if you’re just applying it differently.

The article responds directly to Anthropic’s Jenny Wen’s interview. Wen’s advice works because she’s a senior designer inside a well-resourced AI company with strong design culture. But we only hear about the wins. The solution-first prototypes that went nowhere, the features that shipped and saw no adoption, don’t make it into any public interviews. Most teams don’t have Wen’s conditions. And even inside teams that do, the advice assumes seniority. Junior designers haven’t accumulated the experience that make compression possible. They’re being told to skip a step they haven’t taken yet.

The Sonos app disaster taught me something about roadmaps. Leadership kept adding initiatives—Sonos Radio, the Ace headphones—without ever naming what those additions displaced. QA got squeezed. Stability testing got cut. The designers who warned them were overruled. No leader said out loud what was being sacrificed to make room.

Yusuf Aytas names exactly this failure:

People like to talk about priorities as if the main problem is choosing what matters. In practice, the deterministic factor is capacity. Team capacity. System capacity. The share you lose to maintenance, interruptions, coordination, and keeping the machine fit to run. Ignoring these physical limits turns an ambitious roadmap into a collective illusion.

“Collective illusion.” That’s the right name for it. Aytas on where the dishonesty starts:

A new customer request appears. Leadership wants a visible bet. Sales needs something for a deal. Everyone talks about importance. Almost nobody says what gets pushed out. That is the real decision. They have only added pressure and left the team to absorb the contradiction later.

Aytas builds the whole piece around a carpentry metaphor—one saw, limited operators, timber that needs oiling and adjustment before it can be cut. Software hides the constraint better, but the physics are the same. There’s more in the piece on shaping work before it competes for capacity, using visible investment buckets, and why reallocation is never free.

StrongDM built a system where humans never write code and never review code. The entire engineering workflow is delegated to AI agents. Ethan Mollick covers this in One Useful Thing:

A three-person team at StrongDM, a security software company focusing on access control, announced they had built a Software Factory — a way of working with AI agents that relied entirely on the AI to write, test, and ship production software without human involvement. The process included two (quite radical) rules: “Code must not be written by humans” and “Code must not be reviewed by humans.” To power the factory, each human engineer is expected to spend amounts equivalent to their salary on AI tokens, at least $1,000 a day.

$1,000 a day per engineer. The humans write the roadmap; coding agents build the software while testing agents spin up simulated customer environments and stress-test it. The agents loop until the results pass, then humans review the finished product, never the underlying code. Simon Willison and Dan Shapiro both observed the Factory in operation and wrote detailed accounts.

Mollick’s larger argument is that experiments like this matter beyond their specifics:

We can see the shape of the Thing now, but we can still influence the Thing itself, and what it means for all of us. We clearly don’t have rules or role models for how AI gets used at work, in schools, or in government. That’s a problem, but it also means that every organization figuring out a good way to use AI right now is setting a precedent for everyone else. The window to shape the Thing may not last long, but it is here now.

Design doesn’t have its rulebook for this yet either. Our time to define it is now.

Font selection is one of those workflows AI should have improved years ago. You know what you want the type to feel like. The search box wants you to filter by classification and weight.

Natalie Fear, writing for Creative Bloq, interviews Monotype’s Chief Typography Officer Mike Matteo:

The old way forced creatives to think like a database. You had to know the right terminology, navigate rigid filters, and still, you ended up scrolling through hundreds of options that didn’t quite fit. The creative brief in your head (‘something warm but modern, confident but not aggressive’) had no real translation into a search box. The process was slow, imprecise, and honestly a creativity killer.

Monotype’s new AI search accepts natural language instead. Matteo on what that unlocks:

AI tools have shifted the focus from searching to thinking. Creatives can stay in the idea and brainstorming phase longer instead of getting pulled into the mechanics of finding and managing assets. The tools are finally starting to adapt to how people think, rather than the other way around.

“Searching to thinking.” Monotype made the search box understand what you mean. The rest of the workflow stays the same. More of this, please.

Forty-four UI panels generated in ten minutes, each one grounded in real customer research. Jason Cyr, writing for The Human in the Loop, on what happened when his team pointed Claude Code at Cisco’s design system:

Last week, one of my design directors pointed Claude Code at Magnetic and asked it to build a security detection prototype. Real components, real navigation, theme switching, working admin panels — running in ten minutes. Then he connected it to our research repository and it built 44 detection detail panels, every design decision tracing back to something a real customer said. That happened because the AI had access to our design system.

Cyr’s takeaway: the design system was the design review.

Your design system is your leverage. It’s how your taste scales. The teams that invest here will see their design decisions show up in every agent-generated output, automatically. The teams that don’t will spend all their time cleaning up messes that a good system would have prevented.

Monday.com arrived at the same conclusion from the engineering side. They built a design-system MCP after their agents kept hardcoding colors and ignoring typography tokens.

Cyr doesn’t shy away from who this leaves behind, either: designers whose value lives entirely in production. “Not because they’re bad at their jobs — but because AI just got very good at theirs.”

David Hoang, writing for Proof of Concept, proposes a squad model for tackling a company’s hardest, most ambiguous problems:

The squad: a forward deployed engineer, a forward deployed designer, and a researcher. Three people. That’s it. They operate like a startup-within-the-company, deployed against a specific, ambiguous problem. […] This is a product discovery team with teeth — they don’t just produce insights and hand them off. They produce working prototypes and validated direction. […] Three people don’t need standups, retros, or Jira boards. They need a shared problem and a whiteboard.

No PM. The shared problem replaces the roadmap, and a researcher replaces the product manager. Hoang borrows the concept from Palantir’s Forward Deployed Engineers and extends it to design. His argument: AI tools have given designers enough technical leverage to prototype at engineering speed, so the designer who finds the problem can build the first cut of the solution.

A three-person team with AI tools in 2026 can cover the ground that used to require a ten-person cross-functional team. That’s the direct result of collapsing the build cost of exploration.

Hoang argues that the rotation model matters as much as the squad composition. Four to eight weeks, then disband. The team doesn’t calcify into a feature factory. Designers rotate through the company’s hardest problems instead of sitting on the same product team filing tickets for years.

Although, my counter to that would be designers sitting in the same problem space will gain deeper knowledge and context. Rotation could be counterproductive if not handled deliberately.

I’ve argued that design tools should be canvas-first, not chatbox-first. Jeff, writing in Abduzeedo makes the case for the opposite:

Designers have always borrowed from developers. Version control, component systems, token-based design — these ideas crossed the aisle from engineering and reshaped how visual work gets done. Vibe designing follows the same logic. Instead of opening Figma and reaching for a drag-and-drop panel, designers drop into the terminal. They prompt an AI model directly from the CLI, pipe the output into a file, and iterate without ever touching a mouse.

He isn’t theorizing. He published this article using browser automation and AI, with minimal manual clicking.

I don’t think the answer is CLI or canvas. It’s both. Designers are visual thinkers—that’s the cognitive foundation of the discipline, not a limitation to engineer away. Going fully terminal assumes we can be retrained to work without seeing what we’re making, or that the profession will attract people with entirely different skills.

What does look right is the plumbing underneath. Jeff on Paper.design’s MCP integration:

Its canvas is built natively on web standards — HTML and CSS — which means AI agents working through Paper’s MCP server can read and write design files directly. Tools like get_screenshot, get_jsx, write_html, and update_styles give Claude Code or Cursor direct read-write access to the design canvas.

HyperCard figured this out in 1987: direct manipulation on top of a scripting layer. The tools are finally catching up, with AI as the scripting engine.

Intercom’s design team published numbers that show what happens when agents take over the build. John Moriarty, writing for Fin Ideas:

At Intercom, how we design and build software is unrecognizable from 12 months ago. Our engineering team is already at the point where 90% of pull requests are authored by Claude Code, part of an internal initiative called 2x, where the explicit goal is to double productivity using AI.

When 90% of your pull requests are AI-authored, the designer’s job changes whether you update the title or not. Moriarty’s framework for what comes next:

As the rate of execution accelerates, the role of design becomes sharper. Agents can generate artefacts, but they cannot decide which problems matter, set intent, resolve trade-offs, or hold the bar for quality. Our craft shifts with that reality. […] Agents will own the middle, the build. Design’s value concentrates at the edges, deciding what to build and then determining whether the output is good enough.

Design’s value lands at the edges, not the middle, and Intercom is already adapting their infrastructure to match. They’ve repositioned their design system as what Moriarty calls “agentic infrastructure”:

In a world where Agents write most of the code, design systems become the infrastructure that protects quality. Components, libraries and guidelines are the foundation that Agents and teams build on top of. The better the system, the better everything produced. Strong systems allow quality to scale without adding review overhead.

This tracks with the argument that design systems are becoming AI infrastructure—and Intercom is running it in production. The design system is the quality control layer that lets agents ship at speed without designers reviewing every screen.

Moriarty’s full piece covers how they’re restructuring day-to-day work—moving designers into code, treating Figma as a whiteboard, running structured AI fluency training. Worth a full read.

There’s a distinction between designers learning front-end engineering and designers directing AI agents that produce code against a design system. They sound similar. They share a prerequisite: understanding the material you’re working with.

Adam Silver builds his argument on Frank Chimero’s essential essay “The Web’s Grain”:

The web is a material. Like wood, it has a grain. You can work with it or fight against it.

Silver borrows Chimero’s term for what happens when you fight the grain:

It is very impressive that you can teach a bear to ride a bicycle, and it is fascinating and novel. But perhaps it’s cruel? Because that’s not what bears are supposed to do. And that bear will never actually be good at riding a bicycle.

He makes this concrete with native form controls:

Most designers I worked with hated how the native <select> dropdown looked. So they designed a custom one to make it look good and match the brand. But that meant having to abandon the native element and build a custom dropdown from scratch. Even if you ignore the extra work, you lose: Keyboard navigation, Screen reader support, Automatic form submission, The native iOS scroll wheel, Functionality without JavaScript. Some of this is hard to recreate, some of it is impossible.

This is one of those fights that never ends well.

I agree with the diagnosis. Material literacy matters. Where I part ways is the prescription. Silver’s answer is to design in code using the GOV.UK Prototype Kit. That made sense when writing code was the only way to feel the grain push back. But directing an AI agent to build against a design system gives you the same feedback. You see what the browser does with your layout. You discover where the grain resists. You just didn’t write the CSS yourself. And that’s where we’re headed.

The more interesting question is one Silver points toward without arriving at: AI is a new material with its own grain. It’s probabilistic. It favors volume over precision. Designers who fight that grain — demanding pixel-perfect fidelity from a generative tool — are making the same mistake in a different medium.

Proprioception is the body’s sense of where its parts are in space. Marcin Wichary borrows the term for software that knows where its hardware lives: where the buttons are, where the ports are, where the camera is. His proposed design principle:

The rule here would be, perhaps, a version of “show, don’t tell.” We could call it “point to, don’t describe.” (Describing what to do means cognitive effort to read the words and understand them. An arrow pointing to something should be easier to process.)

Wichary walks through a series of examples, mostly from Apple: the Apple Pay animation that points at the side button, the iPad camera prompt that points to the physical lens, Dynamic Island camouflaging missing pixels as a functional UI element. The one that caught my eye is the device Simulator matching the physical dimensions of your actual phone on-screen and staying accurate even when you change the display density. Reminds me of one of the earliest selling points of the Mac’s 72dpi—it matches the real world: 72 points to an inch.

The MacBook Neo is where Wichary applies the principle and finds Apple falling short. The new model has two USB-C ports with different speeds, and macOS notifies you with text:

I think this is nice! But it’s also just words. It feels a bit cheap. macOS knows exactly where the ports are, and could have thrown a little warning in the lower left corner of the screen, complete with an onscreen animation of swapping the plug to the other port – similar to what “double clicking to pay” does, so you wouldn’t have to look to the side to locate the socket first.

Karo Zieminski spent nine days breaking Claude Cowork before writing this guide:

I’ve seen enough of shallow tutorials that simply rephrase the official docs to know I wanted to do something different. So I rebuilt some of my workflows from scratch, tracked what failed, measured what saved time, and mapped 56 practical tips into the resource I wish existed when I started.

I appreciate her methodical breakdown of the app, especially when to use which flavor of Claude, which for me TBH, has been an issue.

Zieminski’s nice breakdown of the differences between Claude Chat, Cowork, and Code.

The guide barely talks about prompting. It’s almost entirely about the pre-work: dedicated folder structures, global instructions via CLAUDE.md, chunked skills, delegation patterns that define end-states instead of steps. The distinction Karo draws between Chat skills and Cowork skills:

Skills in Chat were useful. Skills in Cowork are operational. They shape autonomous work. Your brand guidelines skill doesn’t just influence a reply. It governs every file Claude creates. Your writing guidelines skill doesn’t just shape a draft. It governs every article Claude writes autonomously.

Zieminski on skill architecture:

Chunk your skills instead of building one giant skill that tries to handle everything. I’ve tested both approaches and the results from one giant skill were much worse. For example, I use three separate writing skills instead of one: an overall voice skill, a corporate writing skill, and a newsletter writing skill. Each handles its own context. Claude never confuses who I’m writing for.

If you’re already using Claude Cowork or just Cowork curious, bookmark this one.

Thu Do set up Figma MCP + Claude Code and audited her entire design system in 10 minutes. The setup took 4 hours. But the reframe she arrives at matters more than the tooling:

Design tokens used to be “nice to have” for consistency. Now they’re infrastructure for AI-to-code-to-design workflows. AI agents read tokens to understand design intent. Proper tokenization = accurate code generation. Inconsistent systems = AI making wrong assumptions.

The bar for design systems just shifted from visual consistency to machine readability.

Buzz Usborne on what happens when AI takes on more responsibility in a product:

AI doesn’t simply make products smarter — it redistributes thinking and decision-making between humans and machines. When AI absorbs cognition, it also inherits responsibility. And when it inherits responsibility, the cost of its mistakes rises.

Usborne frames this through three forces that determine whether AI features survive or fail: trust, value perception, and cognitive effort. They amplify each other. Low trust increases perceived effort. High effort reduces perceived value. Low value further undermines trust.

His answer is to earn autonomy through interaction, not demand trust upfront:

Trust does not always need to precede adoption, it can emerge through usage. Salesforce’s findings show that “Human validation of outputs is the biggest driver in trusting the outcome, over consistently accurate outputs.” In other words, users trust systems they can interrogate, shape, and verify. And instead of designing AI products that are perfect, we can earn trust by designing experiences that are controllable.

Controllable over perfect.

Most product teams adding AI start by building a new surface for it. A custom panel. A chat sidebar. A dedicated AI workspace. Alexandra Vasquez, writing for Bootcamp, describes her team making exactly that mistake:

We built a custom AI panel with its own navigation, input styles, and button treatments. It looked “futuristic” in the prototype. In user testing, people kept asking where things were and how to get back to their actual work. We had created a separate product inside our product.

The fix was simple: they deleted the panel and put agent actions in the same menus, modals, and toolbars people already used. Slack does this with its /command structure. Notion uses the same slash menu for manual and AI actions. The pattern is existing UI that happens to be smarter.

Vasquez argues most “AI failures” are actually system failures that agents expose at scale:

Designing for agents means treating information architecture and workflows as foundational. Before building an agent, audit your system’s foundations: Are labels consistent? Do hierarchies make sense? Can a new team member navigate workflows without constant help? If humans struggle, agents will fail faster and at scale. Fix the system first.

She’s right. And there’s a more radical version of this: agents don’t need human UI at all. As long as the APIs are available, an agent can complete tasks without ever touching a button or reading a screen. The interface is for the human, not the machine.

But that’s exactly the problem. If the agent bypasses the interface, the human’s ability to express intent and verify output becomes the whole game. Intent has to be crystal clear. Feedback has to be immediate and legible. And there’s a huge amount of trust to earn before anyone is comfortable letting an agent operate in the background on their behalf. Vasquez lands here too:

The AI model is the last thing we discuss, not the first. These are product decisions, and designers have outsized influence here.

The model is the least interesting part. The interesting part is designing the trust.

My advice to young designers has always been: start at an agency. You get breadth, exposure to different industries, a pace that forces you to think on your feet. The best designers I know honed their craft in these forges, at shops exactly like the one Madison Utendahl built.

Madison Utendahl, writing for It’s Nice That, describes shutting down Utendahl Creative—ten people, all women, Brooklyn, every award possible—not because it failed, but because she saw the model underneath it was broken:

Lower fees mean you need more clients to hit the same revenue. More clients means more pitching, more account management, more context-switching. Your team burns out. Quality slips. And those “portfolio piece” clients? They expect the same level of work as your premium clients, but you’re doing it on a shoestring. You can’t win.

She watched agencies with triple her headcount bidding on $80K projects that should have been $250K. Not because they wanted to. Because their fixed costs gave them no choice.

Then AI accelerated the timeline:

Clients are using AI. They’re running their first drafts through ChatGPT before they even send the brief. They’re generating moodboards with Midjourney. They’re asking why your junior copywriter costs $8,000 when they’ve already got a version they generated in ten minutes.

Utendahl again:

If your business model depends on clients not noticing that the landscape has shifted, you’re already dead. You’re just still moving.

The industry data backs her up. 73% of teams adopting AI agents have already cut agency content creation spending. 91% of senior agency leaders expect AI to reduce headcounts, and 57% have paused entry-level hiring. Small agencies are rebounding while medium and large agencies contracted for the first time on record. The Omnicom-IPG mega-merger eliminated roughly 4,000 positions and retired legacy networks FCB, MullenLowe, and DDB. The middle is hollowing out.

Utendahl’s proposed replacement is the collective: independent contractors collaborating per-project, no shared overhead, honest pricing. I get the appeal. Collectives strip away the margin squeeze, the back-hiring trap, the lease signed in 2019.

But agencies had real value that collectives don’t automatically replicate. Multiple layers of eyes on work—account director, creative director, designer, production—meant bad ideas got caught before they shipped. Four or five layers was probably too many. But zero layers of structured oversight is the other extreme. A lot of freelance collectives end up there: talented people producing work with nobody checking the brief against the output.

The part that nags at me: does my “agencies first” career advice still hold? The shop where a 23-year-old designer learned to take feedback, iterate under pressure, and watch strategy translate to execution—if that shop is closing, what replaces it? Collectives are great for experienced practitioners. They’re terrible at developing junior talent, because nobody in a collective has the margin or the mandate to train someone who isn’t yet pulling their weight.

If the model has indeed broken, the replacement that develops the next generation has yet to be imagined.