Notes
Notes
Each of these is a position I would defend, compressed to the point where the reasoning is still visible.
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01
Autonomy is earned, not granted
Written 2026
The permission a system holds should track the consequence of what it does. A summarisation can go wrong quietly and cheaply. A payment cannot. The more consequential the action, the more permissions, observability, determinism and reversibility the system needs before it acts unsupervised.
The usual objection is that this slows adoption. It does. It also means the first serious failure does not end the programme. Most organisations only get one chance to be wrong publicly with an autonomous system, and they spend it early.
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02
Once and ten thousand times are different engineering problems
Written 2026
Doing something once tolerates a person watching, correcting, and quietly handling the case nobody anticipated. Doing it ten thousand times does not.
At that volume the edge case has to be handled rather than absorbed, failures have to be visible without anybody looking for them, and the cost per run has to be something the business can carry. Almost all the difficulty in shipping agent products lives in that gap, and almost none of the public conversation does.
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03
Most enterprise architecture is an artefact of a vanishing constraint
Written 2026
The shape of business software was set when computation was expensive, integration was painful, and every capability had to arrive as a separate application with its own screens, its own data and its own login.
Those constraints are weakening. The shape has not moved with them. If you treat the application as the end state you build a better application. If you treat it as an interface abstraction you ask what it was standing in for, which is a different and more useful question.
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04
The answer arrived from somewhere else
Written 2026
Natural language generation was the weak link at Penser. Everything up to the finding worked. Saying the finding back to a person in ordinary language did not.
The first widely available LLM arrived in June 2020, roughly three months after Penser closed and Vipani began. The problem we could not solve was solved by people who were not solving our problem, and arrived after we had stopped. That is worth sitting with rather than tidying into a story about foresight.
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05
A closed question is not a finished one
Written 2026
The mechanism that closed the natural language generation problem exists and is widely available. The next version of Sherlock my co-founder and I wanted is now possible.
Analytics and data science systems which interact with an end user are still lacking. The gap between a mechanism becoming available and a good product existing is not a small implementation detail. It is most of the work, and it is where the interesting problems have moved.
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06
Who absorbs what was removed
Written 2026
Simplification programmes are usually measured on the party that got simpler. That is the wrong side of the ledger. Complexity has a floor set by the task, and below that floor the only thing a system can do is move work from one party to another.
So the audit question is who absorbed what was taken away. A government simplifies its processing by asking citizens for more evidence. A product cleans up its screens by sending the residue to support. Automation handles the routine case and leaves an operator the exceptions, with skills that have decayed because the routine cases stopped arriving. If you cannot name the party that took on the removed work, it probably did not go anywhere.
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07
Friction should be classified by what it produces
Written 2026
Friction is treated as a quantity to be reduced, which makes it impossible to reason about the friction that is doing work. Some of it produces nothing and should go. Some produces attention, deliberation, consent, skill or error containment, and removing it makes the system feel better and behave worse.
Shared-space road design is the clean case. Ambiguity is deliberately increased because attention is the safety mechanism, and no usability metric would catch what smoothing it out would cost. The question to ask before removing friction is what this particular friction produces. If the answer is nothing, remove it. If it is safety or comprehension or consent, optimise it instead.
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08
A warning will not fix a slip
Written 2026
Three kinds of failure, three different remedies, and applying the wrong one reliably fails. A slip is a correct intention executed wrongly, and it wants undo, forcing functions and better defaults. A mistake is a correct execution of a wrong intention, and it wants the mental model repaired rather than the warning made louder. A violation is a knowing departure from procedure, and it is almost always an incentive or feasibility problem.
If the approved process takes ten days and the deadline is tomorrow, the workaround is rational, and training will not touch it. Repeated violations are the most useful signal a system produces, because they show where the formal process and the real one have come apart.
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09
State, not persona
Written 2026
Personas are a planning tool that quietly becomes a runtime model, and as a runtime model they are wrong in a particular way. They assign a person a fixed identity when the thing that actually varies is their situation.
The same person is fluent on Tuesday and lost on Thursday because this case is unusual, or because it is eleven at night, or because the last three attempts failed and they no longer believe the result. What matters at runtime is how much they know about this task, how much time they have, what is at stake, how many times they have tried, and how much of what the system needs it already has. None of that is a demographic.