Five waypoints · Dec 2022 → Sept 2026

The trail from a first question to things that run on their own.

What I learned at each waypoint, and beside it, what I built there. I work in technology; all of this was built after hours with an AI as the collaborator. Bring a question you care about.

Trailhead

Most guides show the summit. This one keeps the switchbacks in.

When I started, every good result felt like luck. What changed things was noticing, one habit at a time, where the effort was going and where it could rest. This trail is that noticing, in order.

Nothing here needs a technical background. It needs a question you care about and the patience to let a system grow around it.

Where are you today?

Choose what's true right now. There's no wrong waypoint, only the next one.

When you open an AI chat, you usually…
Does it remember last week?
Does anything run while you're away?
Waypoint 1 · AskTake me there →
Waypoint 1 · Ask

A useful answer, on purpose.

Why it matters: everything downstream is built from the quality of a single exchange. This is where trust begins.

  1. Offer a brief, the way you'd brief a trusted colleague.Audience, goal, what done looks like, what to leave aside, one example of tone.
  2. Invite one question before it starts.A single clarifying question catches most misreads.
  3. Give notes the way an editor would."Keep the second paragraph's tone; shorten the third."
Audience: [who reads this]
Goal: [the one thing it should do]
Done looks like: [format, length, tone]
Leave aside: [what isn't needed here]
Before you begin, ask me one question if anything is unclear.

An invitation for this week: rewrite one question you'd normally ask as a five-line brief, and notice the difference.

What I built here

What my first 1,200 conversations taught me

Looking back through my export, there's a visible month where my messages became longer than the replies. That's where results turned useful. About eighteen months to arrive there. Those conversations later became the first material for the memory at waypoint 3.

Also
The AI Minute: sixty seconds weekly with my team, one real prompt on screen, what came back, the one adjustment.
Feature
Plain chat. Nothing more yet.
Waypoint 2 · Instruct

Say it once, and let it hold.

Why it matters: the effort spent re-introducing yourself each chat can be saved and reinvested in the work.

  1. Write a five-line core.Who you are, how you like answers, what to check first, what to assume, what to do when unsure.
  2. Create one project for one area.Instructions plus two reference files. Live with it a week.
  3. Add a boundary.Where a piece of context applies, and where it can rest.
About me: [two lines; a job title is optional]
How I like answers: direct; recommendation first, then steps, then what to watch for.
Please check with me before: sending, spending, or deleting anything.
Assume: personal life, unless I say it's work.
When unsure: say so, and ask.

An invitation: write your five lines tonight. Notice tomorrow how much less you explain.

What I built here

A one-page core, and a line about where it applies

One sentence in my profile, "assume personal unless I say it's work," kept each area of life in its own room. Nine projects followed: finances, the house, the kids' school search, a newsletter, a garden channel, my own AI setup.

Feature
Profile preferences, and Projects with instructions and knowledge files.
Waypoint 3 · Remember

Files it can read and write.

Why it matters: a memory you can both see and edit turns a helpful tool into a partner that carries the thread.

  1. Make the folder.One router page, a journal folder, three topic files. Plain markdown.
  2. Keep an inbox file.Anything lands there; once a day, ask the AI to file it.
  3. Hold one gentle rule.Topic files describe now. The journal holds the dates.
  4. Bring your past.Export old chats; let the AI write the history, one file per day.
memory/
  CLAUDE.md            ← who I am, where things live
  journal/2026-09-05.md
  personal/finance.md  ← current state
  personal/home.md
INBOX.md               ← anything, sorted later

An invitation: create the folder with just the router page and today's entry. Ask the AI to read both back to you.

What I built here

The vault: 894 days, one file each

Markdown in Google Drive. A router page says where everything lives. The AI read 3,538 old conversations and wrote the history itself. Health stats arrive four times daily; balances arrive read-only. A small daily check leaves a note when a file grows past 40 KB. It changes nothing on its own.

Feature
Drive connector, plus a daily task that files yesterday and refreshes topic files.
Waypoint 4 · Automate

Let it work while you rest.

Why it matters: the morning page that's already written is the difference between a tool you visit and a system that supports you.

  1. Connect one source.Calendar is a kind first choice. The fewest connections that serve the need.
  2. Write one skill.A how-to for something weekly. Its description decides when it's used.
  3. Schedule one prompt.Fixed wording, fixed time, writes to a file you'll read.
  4. Then schedule a companion.A second task that confirms the first ran. A quiet job also pauses quietly; this one notices.
Every weekday at 8:10:
1. Read today's calendar; one line per meeting on why it matters.
2. Read INBOX.md; gather anything marked TODO.
3. Write a 200-word brief: decisions first, then the day's shape.
4. Save to memory/briefs/YYYY-MM-DD.md and email it to me.
If a source is unreachable, name it at the top.

An invitation: schedule the brief for one week. Read it each morning. Adjust on Friday, and let it run again.

What I built here

Fourteen jobs, and one that looks after the others

Brief 8:10, sync 8:30, network watch 7:38, research sweep 7:45, finance reviews weekly through yearly, and one check at 7:25 whose role is to notice which of the others didn't run. Each writes back to the vault; the dashed line is that return.

Learned
One job reported itself "degraded" for six days and everything read it as healthy. Now a missing heartbeat is treated as worth a look.
Waypoint 5 · Ship

Things that exist on their own.

Why it matters: a page inside a chat is easy to lose. A repo, a domain, a site, a video can be found again, shared, and built on.

  1. Choose one domain.Ask the AI to walk you through a repository and a hosted site, click by click.
  2. Write the spec before the code.One input, every step, what the output looks like.
  3. Ask it to show you the live page.After a deploy, have it fetch the URL. Seeing is settling.
  4. Brief your images the same way.Subject, mood, light, camera, what to leave out. Four variations, then refine.
Before writing any code, let's write SPEC.md together:
- The one input the user gives
- Every step, with min / ideal / max
- What can stretch, and what can't
- What the output looks like
Then build the smallest thing that satisfies it. Show me the spec first.

An invitation: pick the smallest thing you'd be glad to have a URL for. Spec it in ten lines. Ship it this month.

What I built here

Seventeen repositories, five domains, four family tools

A school chooser for our district. A daily newsletter on how organizations govern AI. A lab site, and a status page that watches all of them. A recipe-book app that plans dough backwards from dinner time. A Thai coach built on the sentences said in our house. A finance reviewer that advises and never moves money. An animated cooking-film studio with its own channel.

The loop
The status page writes to the vault. The vault feeds the brief. The brief surfaces the next thing worth building.

Five waypoints, one system. Every box began as a sentence to an AI.

Start wherever the questions placed you. The map beside each waypoint is the same drawing, a little more complete each time. By the summit it's the whole thing, and it's yours to redraw.

Find my waypoint again
About

David Hunter

I work in technology and live in South Carolina with my wife and two young daughters. Before this I farmed, played records, and ran imaging systems, and each still shows up in how I build things. This site is a working record, written plainly enough that someone new could follow it.

The Governance Gazette · hunterlabs.org · [email protected]