jbriggs.org

Jonathan Briggs

chief technology & innovation officer — eastside preparatory school

I work at the seam between how a school runs and what it teaches, and I write about how instruction changes when the tools change.

Most conversations about AI in schools begin with cheating. It's the obvious worry, and the wrong starting point. The better question is about mental fitness: what happens to learning when the struggle that builds it becomes optional?

Teaching has always run on proxies — the essay, the problem set, the confident answer in seminar, all standing in for learning we can't observe directly. AI loosens the link between the product and the mind that made it. That doesn't lower the stakes so much as raise them: it asks us to teach with more clarity about what we actually want students to become, and where the effort has to land.

I work on that from two directions — writing about it, and building the tools that test whether the thinking holds. Neither is solved. Both are worth the attention.

Recent writing

Fall 2026

The wind sprint, the grade as a breaking lever, and why the conditions for struggle turn out to be relational, not cognitive.

Fall 2024

Wind sprints, cognitive dissonance, and flow — the felt experience of hard thinking, and why schools should name the discomfort rather than smooth it away.

Spring 2024

The stand-ins teaching relies on, the supports it leans on, and what happens to both when AI makes the proxy trivial to produce.

All writing →

Built

It's easy to have opinions about AI in education. It's harder to build something a teacher will use on a Monday morning. These started as real problems at Eastside Prep.

Rails · MySQL

The information system behind Eastside Prep — courses, enrollments, scheduling, advising, and grades.

JavaScript

Lightweight, client-side tools that surface what Canvas hides — like how long grading really takes by section — running entirely in the teacher's own browser.

Everything built →

Reach me at jonathan.briggs@gmail.com, or read more about the work.