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The Responsibility Shift
March 29, 2026
Responsibility is shifting. Not as a meme, not as ambiguous hype, but in practice. The systems we rely on don’t just mirror behavior. They structure it. In...
The Tell-Tale Signs
March 22, 2026
A useful question to carry into this week: Is this doing what I think it's doing? Not paranoia. Just curiosity. Because several things that looked like one...
Identity as Training Data
March 15, 2026
For decades, companies scraped the web for data. Now they’re scraping something far harder to replace: identity, expertise, and the authority we’ve spent...
The War on Friction
March 3, 2026
In 2026, friction has become the villain. From the Pentagon demanding “frictionless” autonomous systems to lawmakers pushing age verification infrastructure...
Good for Humans and Machines
February 23, 2026
We build tools to serve us. Then we forget to ask who's actually in control. This week, three stories surfaced the same tension from different angles. An...
Terms of Change
February 16, 2026
Who gets to set the terms of change? This week, we saw the same dynamic keep appearing: Crisis narratives create urgency.Institutions negotiate under...
Agency Is Shifting
February 8, 2026
Machines are gaining more of it. Institutions are consolidating it. And learners, teachers, and citizens are being asked to make sense of it in real time. So...
The Sovereign Agent
February 2, 2026
Hey all. This week, a small open-source project crossed a strange threshold. What started as a weekend hack to connect a local AI to messaging apps turned...
Building in Plain Sight
January 25, 2026
Liberating 400+ Issues from Platform Capture Hey all. For the past year or so, I've been working on something that represents both a technical project and a...
Building Capacity: From Analysis to Action
January 19, 2026
Hey all. Welcome to 2026. A lot has happened since we last connected, and I'm ready to share what we've been building. If you've found value in these issues,...
Catastrophic Forgetting
December 14, 2025
Conversations about children and technology have evolved beyond the debate of “access vs. safety.” The real question now is: how do we prepare youth to...
Digital Childhood
December 7, 2025
Protection, Preparation, and Power The conversation about young people in a digital world has shifted from "access vs. safety" to a more nuanced question:...
Bubbles Go Pop
November 30, 2025
The conversation about AI has shifted from "is there a bubble?" to "how does it burst?" But this isn't just financial speculation. It's about what we're...
The Glass City Paradox
November 23, 2025
The Glass City Paradox: When Technology Shines, but the Foundation Cracks We’ve built a City of Glass: dazzling with technological power, but terrifyingly...
We're Building the Wrong Intelligence
November 16, 2025
An AI pioneer says large language models are a dead end. Seven lawsuits allege they've caused deaths. Yet education is building elaborate frameworks for...
Rewilding the Digital Self
November 9, 2025
Our digital worlds are overgrown. Dense with automation, surveillance, and algorithmic intermediaries. But amid the noise, there is an opportunity to reclaim...
The Chaos Engine
November 3, 2025
Every era builds its own engine of progress, and every engine, eventually, breaks down. Last week, we examined the implementation fantasy: the belief that...
The Implementation Fantasy
October 26, 2025
When Policy ignores reality. This week, seven elite universities rejected a federal offer to trade academic freedom for research funding. The same week, the...
The Efficiency Trap
October 19, 2025
The Efficiency Trap: When Shortcuts Lead Nowhere This week brought a perfect storm: Microsoft and Google announced free AI tools for every teacher in...
Building Archipelagos in Surveillance Seas
October 12, 2025
Welcome to Digitally Literate 407. Last week in DL 406, we watched companies refer to guardrails as "competitive disadvantages." This week revealed what...
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