Skip to main content

The Journey

Most posts here are ad hoc: what I learned building with AI that week, some philosophy, a writing lesson, something I came across.

Subscribe via RSS
A skill file is your judgement, written down and executable. Below: forty files over two years, in her own repo she arrives already running, in theirs she arrives with nothing.
Essay

Own your AI skill files, or your job becomes one

12 August 2026
7 min read

A skill file is your judgement, written down and executable. Who owns the repo decides whether that's an asset or an extraction.

Read More
Six people nod at one sentence and mean four different projects. Below: a hard problem has an agreed objective and a disputed route, a soft problem disputes the objective itself, and most AI briefs are the second run as the first.
Essay

Soft Systems Methodology explained: Checkland's 1969 method for AI briefs nobody agrees on

10 August 2026
8 min read

Most AI projects fail on the brief, not the model: six people nod at one sentence and mean four different projects. Soft Systems Methodology, built at Lancaster from 1969 for exactly that, in plain English: rich pictures, root definitions, CATWOE, and how to run it on the next thing on your roadmap.

Read More
AI projects fail on the problem, not the model. Below: RAND's leading root cause is that nobody agreed what problem was being solved, one brief yields four root definitions, and the fourth is never written down.
Essay

80% of AI projects fail on the problem, not the model: Soft Systems Methodology

8 August 2026
7 min read

More than 80% of AI projects fail, and RAND's leading root cause is not the technology: nobody agreed what problem was being solved. Soft Systems Methodology, built at Lancaster from 1969 for exactly that failure, gives you a way to surface the disagreement in an afternoon instead of a year.

Read More
Where I wanted three sentences, I got Proust. Below: a crash stops you and costs minutes, plausible wrong output stops nothing and costs the afternoon, and only one of them is being counted.
Essay

Opus 5 verbosity: where I wanted three sentences, I got Proust

5 August 2026
8 min read

I judge AI models by how often they make me swear. Opus 5 turned swearing into punctuation, and the reason is more interesting than I first thought.

Read More
Kastrup's cosmic mind has no plan. Below: it is instinctive rather than deliberating, nothing is being worked towards, and it is not looking back at you.
Essay

Bernardo Kastrup's cosmic mind has no plan: what analytic idealism actually claims

31 July 2026
11 min read

The most rigorous idealist alive gives the non-duality audience far less than they want: a universal consciousness that is instinctive, has no plan, and is not looking back at you. What he actually claims, why he says it cannot be proven, and the one part that survives whoever turns out to be right.

Read More
Three status labels feeding a parser: two written as Done and Closed bounce off; one written as Resolved with a date passes through into a report.
Essay

My AI Agents Kept Losing My Work. The Fix Is Older Than Computers.

25 July 2026
6 min read

Seventeen finished pieces of work were invisible to my own tracking system, and the cause wasn't effort or memory. A Berkeley talk gave me the name for what fixed it: an ontology. Here's the version that fits a one-person company.

Read More
Split panel: a crossed-out offer that says We sell AI solutions, against a highlighted offer that says Your phone gets answered, every call, day and night.
Essay

The Data Said Nobody's Buying AI. Turns Out I Was Selling the Wrong Thing.

24 July 2026
5 min read

Last week I showed the demand numbers for AI consultancy are dire. This week a veteran operator explained the part I missed: the demand isn't dead, it's mute. Nobody buys AI. They buy outcomes, told concretely enough to defend to a board.

Read More
Conference-thumbnail style graphic: a bordered jamiewatters.work badge, an orange markdown-logo square with the word Markdown, and giant white text reading Go find the customers
Essay

Garry Tan Just Described My Setup. Then I Noticed What He Left Out.

21 July 2026
7 min read

The YC president gave a talk describing, almost item for item, the AI system I already run. The validation lasted about ten minutes. Then I noticed the word neither of us was saying.

Read More
I got phished from my own verified domain. Below: the key leaked by me in public, the domain verified and now the weapon, and it happened faster than any review cycle.
Essay

I Leaked an API Key and It Turned My Own Domain Into a Phishing Weapon

20 July 2026
6 min read

I got phished from my own verified domain, using an API key I'd leaked myself: what actually leaked, how fast it happened, and what I changed.

Read More
A simple data panel: only 8 to 18 percent of small firms pay for any AI, median spend about $28 a month, and only about 8 percent hire a consultant for AI.
Essay

Everyone's selling AI consultancy. The data says nobody's buying.

19 July 2026
4 min read

A $1,000-an-hour AI consultancy playbook is doing the rounds. The demand data, and a friend who sells everything except this, disagree.

Read More
The map is a file. It outlasts every company that might have owned it. Below: a friend said it should be a business, I assessed it honestly and decided it was not, then built it anyway.
Essay

A friend said it was a business. I decided it was not, and built it anyway.

19 July 2026
3 min read

A friend said it should be a business. I assessed it honestly, decided it was not, and built it anyway because it still needed to exist.

Read More
Essay

You Are Not the House You Built

26 April 2026
4 min read

The third in a series. The performed self is a building you put up because contact with the real one was unbearable. Stopping it from falling down is why you are so tired.

Read More
Essay

If It Makes You Angry, It Isn't Yours

25 April 2026
3 min read

Anthony de Mello said you know someone has been brainwashed because they get angry when you challenge their beliefs. Social media and AI have made the condition almost universal.

Read More
Essay

Contact Is the Test

18 April 2026
4 min read

Self-awareness that doesn't produce contact with other people has gone bad. Dostoevsky figured this out in 1864.

Read More
Essay

Truth Is the Currency of the Future

19 March 2026
6 min read

I'm betting my family's financial future on truth. Here's why I think you should too.

Read More
← PreviousPage 3 of 3