Blue Grotto, Capri Island, Italy • Detroit Publishing Co. • ca. 1900

The Compass of Failure

We tend to see failure as an endpoint: a closed door, a dead end, a signal to turn around and try something else. For much of my life, that’s exactly how I viewed it too. A failure meant I wasn’t good enough, smart enough, or disciplined enough. It was a judgment, not just on what I did, but on who I was. Over time, however, I’ve discovered something unexpected. Failure has often been my most reliable compass, pointing me toward paths I might never have discovered otherwise — paths that felt more like me and brought real joy into my life.

June 14, 2025 · 7 min
From Examples of Chinese Ornament • Owen Jones • 1867

AI Won't Replace Teachers (But It Will Make Us Better)

Every time I show other teachers how I’m using AI in my classroom, I can see anxiety flash across some faces. It usually happens right after they witness an AI-facilitated student conversation that shows surprising depth, personalization, and responsiveness. Sometimes they come right out and say it: “If AI can do this, what’s left for me?”

May 24, 2025 · 7 min
The Cubies' ABC • Earl Harvey Lyall • 1913

Taking Students Seriously

Every teacher has to figure out who they are and how they best interact with students. For me, looking back after 23 years in the classroom, that journey quickly led to a realization: young people get a lot of empty praise. When everything is celebrated at the highest level, genuine feedback becomes meaningless or expected. That approach simply doesn’t work for me in terms of both personality and educational philosophy, and I don’t think it works for my students, either.

May 10, 2025 · 5 min
Slay the Spire, by Mega Crit Games

The Mindful Roguelike

My mental health toolkit includes meditation, journaling, a bit of exercise, and — every day, almost without fail — about 45 minutes with a brutally difficult card-based video game called Slay the Spire. What started as a pandemic coping mechanism has evolved into an essential ritual that’s now woven into the fabric of my life.

April 27, 2025 · 5 min
Blue Knight Mask • Minya Diéz-Dührkoop • 1924

Ubiquity's Cost

Lately, I’ve been noticing how much emotional stress technology places on people across all demographics. Technology increasingly shifts burdens onto users by design, creating anxiety and exclusion—particularly for those less comfortable navigating digital spaces, and I believe that it’s time to recognize and reverse this trend.

April 12, 2025 · 8 min
Detail from Composition No. 61 • Stuart Walker • 1939

The Hidden Advantages of Being a Generalist

“It’s because you’re a generalist.” When my friend made this observation about my success with AI, I stopped for a beat. I was sharing my excitement about all the ways AI was transforming my work and creative processes, but I hadn’t connected it to this fundamental aspect of who I am.

March 30, 2025 · 5 min
Fern Pochoir Pattern • E. A. Séguy • 1914

Wrestling with the Ethics of Generative AI

I’m preparing to teach a unit on AI literacy to a group of high schoolers next month, and it’s clear that we need to spend some of that time discussing the ethics of using Large Language Models (LLMs) like ChatGPT. I’m still working through this stuff myself, particularly because students are sharing their own opinions about it and getting me thinking, so I thought I would take this opportunity to carefully consider the ethics of this type of AI, both as a teacher and as someone who uses LLMs regularly.

March 9, 2025 · 12 min
Ole Worm's Cabinet of Curiosities • 1655

Curiosity's Endless Adventure

As a teacher, I’ve witnessed countless moments where curiosity transforms learning from a task into an adventure. One story particularly stands out. In my Tech Projects class, I had a student who was paralyzed by the blank canvas of possibility. The course begins with complete freedom to choose any technology project, and for this student, that freedom felt overwhelming. Nothing seemed quite right.

February 22, 2025 · 5 min
Eye Test Chart • George Mayerle • 1907

The Power of an LLM Debrief

I spend a lot of time thinking about what works in my classroom and what doesn’t. Sometimes it’s obvious - like when a project catches fire and students can’t wait to dive in. Other times, it’s harder to pin down why something that looked great on paper just didn’t land. I need help to see things clearly. That’s why I’ve always valued getting feedback on my work.

February 9, 2025 · 6 min
Dr. Syntax • Thomas Rowlandson • 1813

Building My Corner of the Small Web

When I first got onto the World Wide Web, one of the things I liked best about it was that it was, in so many ways, completely bonkers. People were putting up weird stuff, wonderful commentary, exciting new ideas, and just being themselves in a way that was suddenly accessible to everyone around the world, including me, sitting at a computer in my tiny apartment.

January 18, 2025 · 5 min