From a chat window to agents that follow the rules
Late 2022. A failing pipeline, a dozen browser tabs, and a new thing everyone is talking about. I type my question into ChatGPT, and an answer comes back written just for me. It's confident. It's clear. And, as I'd soon learn, it isn't always right.
That's where this story starts. It ends four years later with AI agents that read the repository, follow written standards, run their own checks, and deliver platform code and whole applications for me to review.
The other tracks on this site teach a skill. This one tells how I learned one: what I tried, what failed, and what I'd tell you if you're at the same stage today. I didn't plan any of it. Each stage happened because the one before it hit a limit, and the way forward was always the same: give AI better context, and keep a human in charge.
In short: curious → copy-paste loop → co-worker → writer → planner → agents → standards → builder. Each step gave AI a little more context and a little more responsibility.
Read it, then try it
Every chapter is built the same way, so it's quick to read and easy to use:
- A story opening: the moment that stage began, in a few lines.
- What changed and why, in plain language, with a diagram where it helps.
- Try it in your workflow: a small exercise, folded away, to do on your own real work.
- What I'd tell you: the short version, if you're at that stage now.
- What would you do? Three quick scenarios at the end. Pick an answer and see why.
Pick your starting point
- Barely used AI at work yet? Start at Chapter 01 and read in order.
- Pasting errors into a chat window and copying fixes out? Go to Chapter 03, then 04.
- Using AI daily, but only for code? Try writing and planning in Chapters 05 and 06.
- Ready for agents in your repositories? Go to Chapter 07 and 08.
- Just want the summary? Read Chapter 11 first.
Curious (late 2022 to mid 2024)
A DevOps engineer with plenty of problems, a new chat window, and no idea yet what it was good for.
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01
Start here →
Before AI: How I Worked Without It
A failing pipeline and a dozen tabs. The three costs that ate my time, and why your own starting point matters.
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02
Read chapter →
First Conversations: Trying ChatGPT in Late 2022
One clear answer instead of ten links, the first confident answer that was wrong, and the habit that came from it.
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03
Read chapter →
The Copy-Paste Loop: Debugging by Hand (2023 to Mid 2024)
Paste the error, copy the fix, repeat. Why it went round in circles, and the lesson behind everything after it.
Working together (late 2024 to early 2026)
AI stops being a search box and becomes a colleague: one who debugs with me, writes with me, and helps me plan.
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04
Read chapter →
AI as a Co-Worker: Debugging Together
From "fix this" to "help me think": the debugging brief I still use, and why I still own the fix.
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05
Read chapter →
AI as a Writer: Documentation That Finally Gets Done
I bring the facts, AI brings the shape. Runbooks, guides, and training material, and the one rule every document follows.
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06
Read chapter →
AI as a Planner: Breaking Down Big Work and Cutting Cloud Cost
Reading complex requirements, building a work breakdown structure, and finding cost savings to check.
Agents (late 2025 to 2026)
AI starts doing the work itself, so the rules have to be written down and enforced.
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07
Read chapter →
Compliant by Design: An Agentic Workflow for Platform Code
An agent delivers platform code, and the standards, checks, and review gate are built into the workflow.
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08
Read chapter →
Context for Agents: AGENTS.md, Skills, and MCP
The onboarding note, the procedures, the tools, and the hooks that can't be skipped, using this website as the example.
Standards and building (mid 2026)
The loop closes: AI helps write the standards, and the standards make it safe to build whole applications.
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09
Read chapter →
Writing the Standards: Platform Docs, ADRs, and Changelogs
Documentation that serves people and agents alike, and standards that improve every time something goes wrong.
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10
Read chapter →
Building Web Apps for SOC Compliance, with a Full Security Audit
Two real products, the controls designed into them, and the critical bug only a deliberate audit found.