The Best Tools Come to You

What Markdown, Aperture, and Claude Cowork have in common—and what Joe Gebbia's White House gig gets wrong.

This week’s big idea emerged from different angles: the best tools come to you.

It was really Daniel Kennett who came up with the idea in his retrospective on Aperture. Apple’s discontinued prosumer photo app let you edit images wherever you were inside the program—on the map view, in its book editor, while browsing on the light table. You didn’t have to context-switch into “editing mode” like Adobe Lightroom. The tool came to you. A decade later, nothing matches it, and Apple replaced it with something demonstrably worse (Photos).

Aperture failed commercially, but the principle didn’t. Anil Dash’s history of Markdown tells the success version of the same story: a plain-text format John Gruber made up in 2004 now powers the trillion-dollar AI industry. Markdown won because it’s invisible infrastructure—it adapts to how people already write instead of demanding they learn an involved new system—just a little syntax. Dash’s line—”the internet gets built by smart people who think of good ideas, then give them away freely, until they slowly take over the world”—is really a story about tools that refuse to get in the way.

That same humility showed up in how Anthropic shipped Claude Cowork in 10 days. They watched how people actually used Claude Code—planning vacations, building presentations, controlling ovens—and built for that behavior instead of correcting it. The product emerged from observation, not prescription. When your users show you what they need, the move is to follow, not redirect.

The implication for design work is significant. Luke Wroblewski’s insight, which I covered in design tools as the new deliverables, is that brand guidelines should become software—systems that generate on-brand assets on demand rather than static PDFs that get ignored or misinterpreted. The deliverable meets you when you need it, in the format you need it.

There’s a dark mirror to all of this. Joe Gebbia’s tenure as Chief Design Officer in the Trump administration is design that imposes rather than adapts—promotional websites for political initiatives while USDS and 18F, the agencies that actually made government services usable, get gutted. Paula Scher’s point stands: you can’t make government “delightful” while stripping food stamps. That’s design serving the administration, not the user. The opposite of meeting people where they are.

Markdown won. Aperture is still mourned a decade later. Claude Cowork shipped in 10 days because someone was paying attention. The best UX comes to you.

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What I’m Consuming

Streets of Minneapolis. Just the other day, I was lamenting to my teenage son—who’s into hip-hop—how there needs to be more protest songs from musical artists, especially right now. Then Bruce Springsteen released “Streets of Minneapolis,” which apparently he wrote and recorded in just a couple of days. Gotta love The Boss. And while this is admirable, hearing from younger artists who’ll reach a younger demographic would be nice. (Bruce Springsteen)

Where all the protest songs are. This morning, NPR’s music critic Ann Powers sent out a newsletter answering the question I posed above. Her point is two-fold: many old guard musicians like Springsteen, Billy Bragg, Dave Matthews, and Lucinda Williams are releasing protest songs; and so are many indie folk artists. She details a lot of who they are and where to find them. (Ann Powers / NPR)

The Adolescence of Technology. In this follow-up to “Machines of Loving Grace,” Anthropic CEO Dario Amodei outlines the profound risks humanity faces with rapidly advancing “powerful AI,” categorizing them into autonomy, misuse for destruction, misuse for seizing power, economic disruption, and indirect effects. He argues that humanity is entering a turbulent rite of passage that demands careful risk assessment, thoughtful regulation, and proactive measures. Amodei proposes a multi-faceted “battle plan” involving AI alignment, interpretability, transparency, and judicious societal interventions like chip export controls and progressive taxation to navigate these challenges and ensure AI benefits humanity. (Dario Amodei)

Text is king. Adam Mastroianni challenges the popular narrative that digital technology is leading to the demise of reading and complex thought. He argues that while some data indicates a slight decline in reading time, book sales and independent bookstores are actually thriving, suggesting that text remains a vital medium. Mastroianni asserts that human desires for deep intellectual engagement are not easily satisfied by fleeting digital content, and that writing is indispensable for processing and preserving complex ideas. Although, I’d argue that we all need to pick up a novel every now and again—myself included. (Adam Mastroianni / Experimental History)

Project Hail Mary. Speaking of novels, I just finished reading this one from Andy Weir, author of The Martian, which was turned into a movie starring Matt Damon. Project Hail Mary is a page-turner and oftentimes laugh-out-loud funny despite the apocalyptic premise. It’s coming out as a movie in March with Ryan Gosling playing the main character. (Andy Weir)