Everything I publish

The feed

The whole long conversation, newest first. Essays, letters, achievements, Quest Hub updates, and quick thoughts that don't need a grand theory before they earn a place here.

23 dispatches so far
Filter to whatever thread you care about. The rest will wait.

Own the stream

All of my thinking and work, without an algo-maniacal platform in the middle.

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Published work

Showing all 23

Quest update

Agent-Native Email

Made it to inbox zero!

On a brand-new inbox. With almost no email. I classified and actioned 49 messages! It only took 14 hours and 8 minutes of active work, spread across 4 days, 21 hours, and 33 minutes, with 67 merged PRs. Oy.

Open in the Quest Hub

Thought

AI @Work

Four characteristics for excellent agent work

I keep finding the same thing: excellent outcomes from agent work require four basic characteristics.

  1. Curiosity. When I’m in doubt or uncertain, I ask the agent. What happened? What’s off? What does it see that I don’t?
  2. Patience. Things will fail and break. When they do, I return to #1 until they don’t.
  3. Attention to detail. I click through the work closely enough to notice what feels off.
  4. Critical thought. I reason through why it’s off and how to resolve it - with #1, of course.

Attention to detail and critical thought are the critical path. One catches the issue; the other makes sense of it. Curiosity helps me resolve it.

There are skills and best practices to working with AI. I still find that every one I’ve learned is mediated through these four characteristics.

If I hit a ceiling or get super frustrated with agentic work, I check which of the four is lagging and go self-resource it.

Permalink

Thought

AI @Work

Managing agents is a context-switching skill

Working with agents creates a granular fragmentation of work. Each agent carries a small stream forward, but I still carry the map of all of them.

Cycling agent tabs in Claude Code or Codex requires rapid context switching: remembering what each agent is doing, what changed, which decision is waiting on me, and where to return next. The work includes directing agents and mentally tracking multiple concurrent streams without dropping one.

That’s a very particular skill set. It’s trainable, but it isn’t intuitive.

Permalink

Newsletter

Thriving with AI

Hello (again), World!

A serious pup scare, an unexpected staycation, and the agent-native email quest that brought me back to writing.

Keep reading

Quest update

Proactive Family Finances

The prototype became a systems audit

The July audit found a substantial build: 5,862 synthesized transactions and 160 categorization rules, but no trustworthy operating loop. A failed derived-layer repair proved that fixes must live in durable rules.

Open in the Quest Hub

Thought

AI @Work

When my agents fail

If my agents fail, first I need to check if I’ve set them up for success.

And when they do fail, I add new guardrails + evals to make sure it doesn’t happen again and I catch it if it does.

Permalink

Quest update

Agent-Native Email

Agent-native email launch fumbled by agent

Thriving with AI launched from the new agent-native stack - and OpenAI's Sol sent the launch email before it was fully complete. The most ironic agent workflow possible is now becoming a stricter dual-inbox test, explicit post-test approval gate, and permanent incident trail.

Open in the Quest Hub

Thought

AI @Work

A cast of agents

I need a better term for a grouping of agents.

Swarm feels like an undifferentiated mass. Team feels too corporate. I tried village for a while, but it never quite sat right. So I had a short brainstorming session with Claude and landed on cast: a cast of agents.

It works for an almost unreasonable number of reasons. A cast is a group of hawks or falcons, which fits because Hawkeye was my nickname for years. A cast of characters is already familiar. You cast a falcon, a spell, or an actor. You cast from a mold. You cast off and release.

It’s not a double entendre. It’s a multi-entendre.

So that’s the language I’m using from here on out: a cast of agents.

Permalink

Quest update

Agent-Native Email

Outbound went live the day the host said no

The hosting provider refused to open direct outbound - so the relay path designed on day one took over. Messages queued for 23 hours flushed in seconds, and the whole stack scored 10/10 on mail-tester. The foundation workstream is complete.

Open in the Quest Hub

Quest update

Agent-Native Email

Four pages designed and built in a day

The launch surface went from route inventory to four reviewed page redesigns in one day - drafted as design cards, edited in a shared design pane, shipped as pull requests. 30 routes went dark; 13 pages remain, crawl-audited clean.

Open in the Quest Hub

Quest update

Agent-Native Email

The server is alive

My thrivinghenry.com mailbox now receives on hardware I control: MX cutover done, first real message delivered in under a second, and an EA agent triaging at 100% on its golden-set eval.

Open in the Quest Hub

Quest update

Agent-Native Email

The trailhead is mapped

Design spec approved before any building: a self-hosted OpenBSD mail server, a newsletter relaunch on owned rails, this quest hub, and a five-seat cast of agents - with success criteria declared up front.

Open in the Quest Hub

Quest update

Proactive Family Finances

Goals became a shared review loop

Goals, watched spending, live metrics, balance snapshots, and commitments came together in one review surface. The breakthrough was treating family finance as a recurring decision ritual, not another dashboard.

Open in the Quest Hub

Essay

The Journey

Thriving, This Time with AI

Five years ago I started writing about thriving without AI. The tools changed. The question didn't. My inaugural essay relaunching my website and newsletter to focus on Thriving with AI.

Keep reading