What broke, what I built, and what I’m still learning.
These five are a good map of the machinery, including why any of it exists.
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.
Grafana dashboards last edited in October. Admin last logged in in October. The database grew for ten months anyway, on the smallest disk in the fleet. Teardown as maintenance.
I thought my smart home had 800 devices. An audit found 1,751 — and 29 of my 42 scripts had never run once. The fix wasn't more automation. It was less.
Bubbles runs on Hermes, lives on a Mac Mini, and has an iMessage number through Photon. The useful part isn't the chat—it's the skills that connect it to the tools I already use.
I gave our family AI access to twenty years of photos. The interesting engineering wasn't what I let it do — it was everything I refused to let it do, and keeping the captioning local so the photos never leave the house.
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.
A container update killed my Cloudflare tunnel by pointing it at a Docker network that no longer existed. Nothing logged, nothing alerted. Four public services, dark for three days.
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.
I tried to get my family AI legally approved to send text messages. Twilio's compliance robot rejected the same field four times, twice after I pasted in its own suggested wording. The robot won.
Every light at the lake place was invisible to voice control, and the setting that should have exposed them had been dead the whole time. Fixed that — then rebuilt the entire voice surface so two grandparents can run the house without ever opening an app.
I audit systems for a living-adjacent hobby, so I pointed the process at my own site. 105 MB homepage, zero analytics ever collected, nine dead blog links. The cobbler's kids, fully barefoot.
The API console showed a key burning $175/month — a key that shouldn't have been in use at all. It traced back to a background 'dream' loop I'd accidentally installed, whose built-in budget guard was under-counting its own spending by 7x.
The family AI now reads everything I know: the kids' summer schedules, project decisions, business questions, years of notes. A searchable brain over my whole vault made it possible — plus two fixes that made it dependable. I love this thing.
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.
My stuff lives in two countries, three time zones, one closet, and a cloud droplet. Tailscale is the reason it behaves like one house — and the one piece of the stack I'd have to replace before anything else could work.
The family AI went silent and everything pointed at an API outage. The actual cause: a debug command I'd forgotten about, hung for 16 days, eating all 16,384 network ports.
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.
My laptop dropped off the network every five minutes at the lake place. 38 hard disconnects in 5 hours, and the ISP, the router, and the laptop all checked out clean. The culprit was where the desk was.
I texted my AI a screenshot and it swore no image arrived. The iMessage adapter was compiled bytecode with no source — it had never handled inbound images at all. So I taught it to, without ever seeing its code.
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.
Somfy's official cloud integration refused to see 18 motorized shades because of an account merger on their end. The way in was an undocumented local API, unlocked by tapping the hub's PIN screen seven times. The workaround ended up better than the front door.
Four Canadian LG air conditioners, installed in Canada, serving Canadians, refused to connect until I told the setup flow they were American. The hardware doesn't matter. The account region does.
The new place in cottage country somehow has 2.5-gigabit symmetric fibre — and a Bell router with no bridge mode. That meant double NAT, which meant Tailscale falling back to relay servers. The fix was a fiber modem the size of a stick of gum.
The lake house had a verified 2.3 gigabit fiber line and every WiFi device topped out at 90 megabits. The internet was innocent. It came down to one keystone jack, and the answer to 'why does the internet suck' was a punch-down tool.
My AI's knowledge base survived its rebuild for 28 hours. Then macOS sent a kill signal mid-checkpoint and corrupted the whole database — for the second time in 24 hours. A forensic timeline, two zombie processes, and an honest ending.
The router at my salon suite location crashed weekly, and the fix everyone assumed was wrong. Behind it all: a missing $2 battery that made the router believe it was 1980. Fifteen days, three visits, four bad hypotheses, one $199 box.
Touch ID for sudo died overnight, with no message anywhere: a macOS security patch had wiped one config file and divorced my keyboard from the Secure Enclave. Thirty-four minutes of file timestamps and Bluetooth forensics to get my thumb back.
463 session transcripts were sitting on my disk as unsearchable JSONL. Now every session that matters gets redacted, graded, summarized by a cheap model, and filed in my notes automatically — 315 notes so far, for about three dollars a month.
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.
I inherited an encrypted backup of a router's config with no password to open it. So I tried to guess. Eleven hundred and fifty-eight guesses later, I did the smarter thing: I stopped.
At 7:48 one morning, Bubbles blew up my phone with texts nobody asked for. The investigation took six and a half hours, ended one entire agent runtime, and produced a rule I still live by: the assistant doesn't get to text me.
The file was indexed. I verified it. And a two-word query still couldn't surface it. A better embedding model wouldn't have helped — what worked was a second retriever with different failure modes, fused by rank instead of by score.
A dozen self-hosted apps, each remembered as a port number. Three pieces closed it out: a wildcard domain resolving to a private address, genuine wildcard certificates issued to a server no certificate authority can visit, and a deploy that reconciles itself.
The AT&T gateway passed its speed test, but my own router could not get online. The fiber provider had authorized one network-port address while the cable was plugged into another.
A power outage took 840 smart-home entities offline with no error anyone saw. The cause was two services wanting one port and an appliance OS that re-enables its own daemon on every boot — so the fix isn't a config change, it's a boot-time reconciler.
Swapping the agent runtime took an afternoon. Re-pointing everything bolted onto the old one took the rest of the day — including scheduled jobs that expired every seven days behind a nightly restart nobody was watching.
Traffic from ten domains I never checked became one plain-language morning email. It showed me that 196 server requests represented only three actual visitors — then ran stale code for two days without an error.
Home-and-away automations were firing for people who weren't there. What worked was a second, independent presence signal built from something I already owned — the WiFi controller — plus an aggregation rule with one sharp edge worth understanding before you use it.
Most people name their NAS nas-01. Mine is Randy, from Trailer Park Boys, because the rule is simple: the character's job on the show is the server's job in the house.