Side Quests

GenAI-enabled side quests: the “why bother” and lessons learned from my AI-Assisted side projects, following “Simon Willison rules”

A wise man said that if you get distracted by a side project, you should at least write about it:

My outputs are more modest than Simon’s, but I’m using AI to cook at a rate I couldn’t have imagined just a few months ago. Apparently the limiting factor is ideas now, so.. let’s roll!

README.md on GitHub explains what and how. These write-ups are the why, the journey, and cool stuff I think I learned along the way.

So far, in January 2026, I’ve:

  • Built a computer vision app, to prove some math inspired by a Mark Rober CrunchLabs experiment (Galton’s Goalie)
  • Migrated a 10,000+ line codebase, twice, to resurrect a passion project originally built by over 50 Engineering students many moons ago (Legend of the Greasepole: Resurrection)
  • Resurrected a Frontpage 98 “museum” site, bringing back a museum of history and optimizing its taxonomy (The LegendWeb: Resurrection)
  • Built a health-system integration that I now use daily, published to the cloud as an AWS Lambda (a technology I’d never touched before (Withings to Garmin Sync)
  • While on a plane, cooked a “Side Quest Helper” that helps me update my WordPress site and document the “why bother” of these experiments (p.s. yes I write these)

My north star: field notes from (near) the frontier of building with AI.

  • LegendWeb: Resurrected

    LegendWeb: Resurrected

    Side quest to a side quest. A 1998 CD-ROM tribute to Queen’s Engineering traditions, resurrected from a FrontPage hot mess with Claude’s help.

  • Legend of the Greasepole: Resurrected

    Legend of the Greasepole: Resurrected

    It’s a 1999 student game about Queen’s Engineering traditions, resurrected 25 years later with AI help. 50 students built it then, AI brought it back now. Play in your browser.

  • Side Quest Helper

    Side Quest Helper

    Utilities to automate WordPress updates, built at 10,000 ft.

  • Withings to Garmin Instant Sync

    Withings to Garmin Instant Sync

    A real-time bridge between Withings scales and Garmin Connect

  • Galton’s Goalie

    Galton’s Goalie

    Today’s Engineering Hustle: Using AI to Upgrade Mark Rober’s “Plinko Machine” from #CrunchLabs, and Visualize the Math in Style