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Roger Wong

@lunarboy.com
279 followers 565 following 527 posts

Design leader writing about AI and the future of product design. 20+ yrs at Apple, Microsoft, Samsung, BuildOps. rogerwong.me

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Roger Wong @lunarboy.com · 30/08/2026
I made the Comic-Con schedule app for myself (and any interested nerds). With AI, anyone can DIY software just for their own needs or a small community. Full newsletter here: open.substack.com/pub/lunarboy...
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Roger Wong @lunarboy.com · 24/07/2026
Token billing/metering. Sounds like they have something cooking already, but OpenRouter could be complementary.
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Roger Wong @lunarboy.com · 23/07/2026
Holy shit. Using the Compound Engineering plugin and Fable, I planned out an iPad port of my app this morning. Then before dinner, kicked off Codex on the goal of implementing it. 4 hours later, it’s alive!!!!
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Roger Wong @lunarboy.com · 23/07/2026
Trying out Codex in the terminal… I'm sorry, but Claude Code is more beautiful and considered. Maybe I'm just used to it, but Codex feels very unfinished from a UI standpoint.
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Roger Wong @lunarboy.com · 21/07/2026
I called it "Galileo" as a nod to the famous astronomer *and* the USS Enterprise's shuttlecraft from #startrek. Hope you like it.
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Roger Wong @lunarboy.com · 21/07/2026
Download it here (sorry, desktop only): github.com/wongdigital/...
github.com
GitHub - wongdigital/galileo: Galileo — Chart your course through San Diego Comic-Con
Galileo — Chart your course through San Diego Comic-Con - wongdigital/galileo
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Roger Wong @lunarboy.com · 21/07/2026
Just in time for San Diego Comic Con! @sandiegocomic-con.bsky.social I made a full schedule explorer app. It's super fast and even contains a relatedness graph view so you can explore by genre, franchise, or even people. Best of all, it's free...
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Roger Wong @lunarboy.com · 20/07/2026
Working on something kind of fun. The @sandiegocomic-con.bsky.social schedule is notoriously terrible. With nearly 3,500 events over 5 days and 51 rooms/venues, it's an information nightmare. SDCC's app and site aren't great. So I decided on Friday to see if I can make a better one. #sdcc2026
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Roger Wong @lunarboy.com · 07/07/2026
Fuller write-up here, with examples: rogerwong.me/2026/07/maco... 3/3
rogerwong.me
macOS Squircle Icons Are Fine - Roger Wong
macOS Tahoe's squircle icon mandate has critics, but there's a real usability case for it: oddly shaped icons have always had awkward click targets that catch users off guard.
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Roger Wong @lunarboy.com · 07/07/2026
You can see that Automator and Chess didn't have the full square click target. Interestingly, QuickTime and Sherlock did account for it. Apple fixes this issue by requiring all app icons to be the squircle, matching iOS. 2/
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Roger Wong @lunarboy.com · 07/07/2026
Regarding macOS Tahoe and the requirement of squircle app icons, I think it's an accessibility play by Apple. Here, in Mac OS X 10.4, I'm trying to click in the blank space around the shape. Didn't work. 1/
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Roger Wong @lunarboy.com · 29/05/2026
My god this is real.
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Roger Wong @lunarboy.com · 18/05/2026
Full newsletter: newsletter.rogerwong.me/p/editorial-... 2/2
newsletter.rogerwong.me
Editorial Is the New Job Description
Coherence is what users feel. Editorial leadership is the work that produces it.
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Roger Wong @lunarboy.com · 18/05/2026
Been writing about designers-as-orchestrators for a year. "Editorial" is the better word. Orchestrator suggests conducting players who already know their parts. Editorial means standing over the whole portfolio, deciding what belongs and what gets killed. 1/2
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Roger Wong @lunarboy.com · 10/05/2026
Designers and PMs are writing markdown files like DESIGN.md or SOUL.md for their agents. The files hold what used to live in our heads as taste. New newsletter: newsletter.rogerwong.me/p/out-of-you...
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Roger Wong @lunarboy.com · 09/05/2026
I mean, let's call a spade a spade. rogerwong.me/2022/08/trum...
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Roger Wong @lunarboy.com · 08/05/2026
You ever get the feeling that Claude Opus 4.7 was trained only on Willam Gibson novels?
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Roger Wong @lunarboy.com · 28/04/2026
Glad I just renewed mine!
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Roger Wong @lunarboy.com · 27/04/2026
Wrote about it in this week's newsletter. newsletter.rogerwong.me/p/the-fricti...
newsletter.rogerwong.me
The Friction That's Missing
The model agrees with everyone. The work asks you to disagree.
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Roger Wong @lunarboy.com · 27/04/2026
Old construction saying: paper accepts everything. AI prototypes now do the same. The discipline is learning what to reject.
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Roger Wong @lunarboy.com · 27/04/2026
AI tools agree with everyone. They're designed to. They remove the friction that used to keep design honest, and whoever learns to put that friction back is doing the actual work.
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Roger Wong @lunarboy.com · 21/04/2026
Spent Sunday afternoon with Claude Design working on my cousin's preschool site. First draft: B-. Four dozen micro-tweaks later: A. The tool gave me a head start. Taste did the rest. rogerwong.me/2026/04/sund...
rogerwong.me
A Sunday Afternoon with Claude Design - Roger Wong
A hands-on look at Claude Design through a preschool website redesign, with reactions from designers on where it fits alongside Figma and Claude Code.
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Roger Wong @lunarboy.com · 19/04/2026
Four designers I'm reading answer at different altitudes. I'm practicing this on a preschool side project: visual language by hand, plumbing handed to the model. newsletter.rogerwong.me/p/sketches-t...
newsletter.rogerwong.me
Sketches Through the Fog
Possible paths for where the judgment goes when AI handles the production.
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Roger Wong @lunarboy.com · 19/04/2026
We're getting good at accelerating design work. Automating it is still hazy. AI will ship a passable prototype in minutes, but it can't tell you where your judgment goes when the model handles production.
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Roger Wong @lunarboy.com · 14/04/2026
Do we want design automated? No. But it's already happening at tech-forward companies. Agentic design is the future; the process to run it isn't fully formed yet. I can see its outlines. rogerwong.me/2026/04/acce...
rogerwong.me
Acceleration Is Not Automation - Roger Wong
AI is accelerating parts of the design and PM workflow, but true automation is still out of reach. Agentic design teams are taking shape, and human judgment remains the bottleneck.
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Roger Wong @lunarboy.com · 14/04/2026
Acceleration is not automation. Engineers crossed the line this year: four agents in parallel, wiped out by 11am. Design hasn't. Faster PRDs and prototypes are acceleration. Automation needs specialist agent teams, with your judgment shaping the output.
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Roger Wong @lunarboy.com · 13/04/2026
More in this week's newsletter. newsletter.rogerwong.me/p/who-teache...
newsletter.rogerwong.me
Who Teaches the Product Builder?
The people succeeding in LinkedIn's product builder program all started as specialists.
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Roger Wong @lunarboy.com · 13/04/2026
LinkedIn's working Full Stack Builders all spent years as specialists first. That's the part of Tomer Cohen's pitch that nags me. They flex because they built taste one lane at a time. The new APB program bets juniors can skip that phase and still develop the judgment. I'm not convinced. 1/
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Roger Wong @lunarboy.com · 12/04/2026
Gen X gets forgotten AGAIN. Thanks @wsj.com www.wsj.com/personal-fin...
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Roger Wong @lunarboy.com · 29/03/2026
This week's newsletter gets into all of it. newsletter.rogerwong.me/p/design-at-...
newsletter.rogerwong.me
Design at the Edges
When agents absorb the middle of the workflow, what's left is what always mattered.
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Roger Wong @lunarboy.com · 29/03/2026
Intercom, Cisco, and Figma all landed on the same answer: design's value is at the beginning and the end. Agents own the middle. The catch: the middle is where junior designers built judgment. We're compressing the workflow and the career ladder at the same time.
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Roger Wong @lunarboy.com · 22/03/2026
When factories got electric motors in the 1880s, they swapped the steam engine and changed nothing else. For 30 years, output barely moved. Most teams are doing the same thing with AI. I wrote more about this: newsletter.rogerwong.me/p/the-factory-hasnt-been-redesigned
newsletter.rogerwong.me
The Factory Hasn’t Been Redesigned Yet
The productivity everyone's chasing lives on the other side of a redesign nobody's started.
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Roger Wong @lunarboy.com · 15/03/2026
Designers, we’re in the messy middle stuck between two ends. Do you defend “designer” as a role or follow the skill of design? I explore this in my latest newsletter.
open.substack.com
Defend the Role or Follow the Skill
The messy middle was never a phase. It was the whole job description.
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Roger Wong @lunarboy.com · 15/03/2026
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Roger Wong @lunarboy.com · 13/03/2026
This method may work for a class of products. But it won’t for vertical SaaS as well, especially if they’re mission critical. Imagine experimenting on an electronic medical record system (nope!) or software for dispatchers. Lots of convos forget about the products that shouldn’t change rapidly.
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Roger Wong @lunarboy.com · 08/03/2026
The design profession got exactly what it asked for: less time pushing pixels, more room for strategy. Most of us are using that time to argue about what designers should be instead. newsletter.rogerwong.me/p/the-territ...
newsletter.rogerwong.me
The Territory You Haven’t Claimed
The tools are ready. The demand is real. So what's stopping us?
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Roger Wong @lunarboy.com · 07/03/2026
I can attest to this. Many of my pieces run 2,000–3,000 words but actual reading time on those posts (from analytics) are always under the calculated reading time.
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Roger Wong @lunarboy.com · 04/03/2026
Jenny Wen’s "ship fast, iterate publicly, build trust through speed" approach makes sense for Anthropic. They're building greenfield AI products where nobody knows the right interaction patterns yet.
rogerwong.me
The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude) - Roger Wong
Jenny Wen leads design for Claude at Anthropic. Prior to this, she was Director of Design at Figma, where she led the teams behind FigJam and Slides. Before that, she was a designer at Dropbox, Square...
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Roger Wong @lunarboy.com · 02/03/2026
In case you’re looking to switch chatbots, say from a four-syllable one to a single-syllable one: claude.com/import-memory
claude.com
Switch to Claude without starting over | Claude
Transfer your preferences, projects, and context from other AI providers into Claude. Switch without losing what makes your AI useful.
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Roger Wong @lunarboy.com · 02/03/2026
That was the first time I’d seen that. So crazy!
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Roger Wong @lunarboy.com · 02/03/2026
Wow. LOL
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Roger Wong @lunarboy.com · 01/03/2026
Either abstain on principle or capitulate for the paycheck. I don’t buy the binary. There’s a third path—use the tools to expand what your craft can produce, and people are already walking it. Read the full newsletter. 2/2 newsletter.rogerwong.me/p/the-grief-an…
newsletter.rogerwong.me
The Grief and the Third Path
The craft you're mourning might not be the craft you're losing.
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Roger Wong @lunarboy.com · 01/03/2026
Developers and designers are independently grieving the same thing right now, and it took me a while to realize they’re not mourning the skill but the tribe. The community that used to care about the craft now feels like it’s about speed, or pulling a slot machine lever on prompts. 1/
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Roger Wong @lunarboy.com · 27/02/2026
I thought the same thing. This might be the inflection point and NOT “AI-washing” as in the earlier layoffs from Amazon, Meta, etc.
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Roger Wong @lunarboy.com · 27/02/2026
www.anthropic.com/news/statement…
anthropic.com
Statement from Dario Amodei on our discussions with the Department of War
A statement from our CEO on national security uses of AI
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Roger Wong @lunarboy.com · 27/02/2026
Boom. I’m glad @anthropic.com is not caving in. Anti-mass domestic surveillance and anti-autonomous murderbots are moral red lines to have.
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Roger Wong @lunarboy.com · 26/02/2026
Best thing I heard today: “Claude Code is gaslighting me.” 🤣
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Roger Wong @lunarboy.com · 25/02/2026
Check out Reader from ReadWise and Inoreader. Both are great. Unsure if either support fetching feeds from an API though.
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Roger Wong @lunarboy.com · 22/02/2026
Just published a new newsletter wrapping up the theme of last week. Design is changing fast due to the new AI tools. Bleeding edge Silicon Valley companies have already made the shift. Our days of drawing pictures of designs to be implemented are numbered.
open.substack.com
Stop Drawing Pictures of Software
AI is pushing designers out of Figma and into the material they actually ship.
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Roger Wong @lunarboy.com · 20/02/2026
Everywhere I look, there’s a new ASCII project. I think it’s sort of a halo effect from Claude Code and the nostalgia designers and developers have for terminals. Anyway, I wrote a roundup of stuff that’s caught my eye. #designsky
rogerwong.me
ASCII Me - Roger Wong
ASCII and text-based art are making a comeback: a personal roundup of ASCII art, animated clouds, glyph tools, Mermaid diagrams, and terminal UIs and nostalgia.
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