The boring stretch is where the partnership shows


Joe Taylor Jr. Newsletter — May 14, 2026
Joe Taylor Jr.

Joe Taylor Jr.

Thoughts on UX, leadership, and building things that matter

Hey

Reader —

My team is shipping more polished work than ever — a personal brand site launched, a therapy practice site reached staging, a community wellness build went from outline to working homepage. By every external measure, it was a great week.

Meanwhile, on my own corners of the internet, I'm watching most of my peers turn themselves into their own film studio. They're shooting Reels in their cars and holding their lavalier microphones too close to their mouths.

My formal training said: do not be in the video. Stay behind the camera. Let the work be the work. The short version of my latest post: staying relevant is, and has always been, an exercise in diving into a new medium every few decades, even when the medium is uncomfortable.

See you on Reels, I guess.

3 Things I'm Thinking About

1
WordPress is 25 years old, and that's the whole point.
I was building custom content management systems from scratch from 2000 to 2003, the year WordPress shipped. Twenty-five years and seven major versions later, it's still been the right answer for roughly nine out of ten projects I've taken on. The thing I keep noticing isn't the software — it's how few platforms get to compound for a quarter-century without burning their users on the way through. The bet you make when you build on something boring and old is that it'll still be there when you need to ship in 2030.
2
I'm going to lose my Tree Runners, aren't I?
Om Malik wrote a piece called "Newbirds AI is Really Loonybirds AI" about Allbirds quietly repositioning as an AI infrastructure company. I don't care that Allbirds fell out of fashion. I just love wearing my Tree Runners any time it's warmer than 70 degrees. The brand pivot speedrun is now a stage of grief. Every brand I built a small attachment to in the 2010s seems to be one funding round away from selling me a chatbot.
3
AI-built sites look professional and fail accessibility audits, and nobody is surprised.
I've watched a wave of novice developers ship sites built with AI assistants that look great and quietly violate WCAG 2.1 on the basics — missing form labels, no focus indicators, color contrast that flunks. It's the same story as every web tool ever pushed at business owners. The pretty surface ships fast. The accessibility, the trust signals, the parts that decide whether your site is useful to the people who actually need it — those still take humans who care.

One Thing I Learned This Week

The boring stretch is where the partnership shows. The week between "we know what we want" and "we shipped it" is where most projects get lonely. The discovery is far behind, the launch announcement is far ahead, and the daily work is small, technical, and easy to deprioritize. I used to think the kickoff and the launch were the moments that mattered. Three sites in three different stages this week reminded me: the people who'll show up for the middle are the ones who'll still be there at the end.

Links That Made Me Stop Scrolling

On the Podcast

Marginally Better S01E17: The Repair Relationship Revolution

A century ago, executives sat in Geneva and signed a contract to make their products worse on purpose. The Phoebus Cartel built planned obsolescence into the modern economy. This episode is about who's tearing it back down — a hundred-year-old cookware company in Tennessee, a laptop startup whose customers help design the next mainboard, and a European law that's about to require every manufacturer to tell you how to fix the thing they sold you.

Listen to the episode →

New on My Blog

Everybody's Cindy Nowadays

Billy Bragg introduced me to Cindy Sherman in 1991. I spent the next thirty-five years carrying a rule from my Television-Radio degree — do not be in your own video — that 2026 has politely informed me is now obsolete. A short essay about pivoting media, the things we learn we have to do anyway, and the unexpected art of writing a script for yourself.

Read the post →

Currently Taking On: A Few Coaching Conversations

I keep trying to wind the coaching practice down, and people keep showing up with the right kind of problem — leadership transitions, deciding what AI belongs in a team and what doesn't, figuring out what the next 14 years of a career actually should look like. If you've been wanting that kind of conversation, the door's still open.

Start a Conversation

Joe Taylor Jr.

I write about what it takes to change your world, whether that's making music, growing a business, or crafting something uniquely yours.

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