What broke, what I built, and what I’m still learning.
Newest first. The useful failures tend to age well.
A global hotkey, a blank note, and it's out of your way — jot. is a scratch-notes app I built in a single Swift file, and my first real native Mac app. It dresses like my terminal, joins the family of little apps we run, and I use it more than anything else I've built.
Jacks' fantasy league runs on a spreadsheet whose rankings are last year's points wearing this year's clothes, with zero rookies in it. So we built a draft kit: four research agents, an offline draft board, and a shot at an unfair advantage.
Nine small self-hosted apps built in four different frameworks that all look like one product. One tokens file, one framework-agnostic switcher, and an icon template specified down to the baseline formula — plus the PWA caches that will happily serve last month's app.
Tasks, groceries, lists, workouts, movies, trips — all self-hosted, all sharing one design system and one icon template. The interesting parts are the cheap AI that writes its answers back to a cache, and the day a grader couldn't pick my new icons out of a lineup.
I built a house-control PWA with optimistic UI, reconnect resilience, auto-rollback deploys, 148 tests and a 52KB bundle. Then an audit asked whether it should replace Home Assistant outright, and the honest answer killed the project.
Southbound counts days spent in Florida. After a user flew to Illinois and back, duplicate calendar dates created across time zones made the iOS app crash before its first screen could open.
My self-hosted task app issues login tokens that last ten years. It logged me out weekly anyway. The token was fine the whole time; the app kept panicking and shredding it.
Every travel tool assumes you already know where you're going. Ours starts at 'someday, Tokyo' and tracks it through to a day-by-day plan — plus the bug where marking a trip booked got un-booked forty-five seconds later.
Taste used to live in my source code, so changing what I like meant editing TypeScript and redeploying. Now it lives in a note in Obsidian, and every app that cares reads it at runtime. The publishing mechanism is 24 lines.
Fourteen data sources, two LLM calls, one email, zero machines I have to keep awake. Every fact is rendered in TypeScript and only the voice is generated — plus the cron bug that sent a Friday email on Thursday for weeks.
My want-to-watch list was sharded across three services, none of which knew what I already owned. So the movie picker kept recommending films sitting on my own server. Building the state layer was easy; making it stop suggesting the same movie every night was not.
Golf throws off enormous data that lives in three places which don't talk to each other. A sweep of my own machines found I'd already built the app in seven disconnected pieces — including a stats file hiding inside another app that explicitly bans golf.
A list of things you might want is not a list of things you must do, and cramming both into a task manager ruins both. So I built a third app — and then discovered the hard part isn't the app, it's deciding which of my six apps a sentence belongs to.
A daily generated workout, a REC mode that holds your screen awake, and a rating you give after the session instead of before. Then the program drifted from reality and the app kept confidently prescribing workouts nobody was doing.
Capture was never the friction in a task app; filing is. So I self-hosted one that files for me, then discovered the more interesting use: my machine agents file tickets in it too, claim them race-safely, and hand work back.
Voice is where groceries actually get added — hands wet, standing at the fridge. But every good list app is a phone app. So I bridged the Echo to a list of my own, and then the purchase history turned out to be the real product.
I keep everything in a pile of plain-text notes. Reading them was boring, so I built a little machine that turns the whole pile into a designed, searchable website — one that rebuilds itself every few minutes and never asks me to change how I write.
Coming back from a shoulder thing, I needed workouts that respected the recovery plan. Every fitness app wanted a subscription and my data. So fit. got built in a day: self-hosted on Randy, AI-generated dailies, one-click logging.