MY AI ASSISTANT KEEPS TRYING TO MAKE ME WORK ITS WAY, NOT MINE
Months after I built my own system for tracking work, the assistant is still pinging me, every session, to use its built-in one instead. I’ve turned off the settings that are supposed to stop this. They didn’t. This is about the four places I keep having this exact fight, why the tool keeps having it with me, and what I actually do about it.
NOBODY ASKED YOU TO CONSENT TO THE JOINS
A friend once asked me what personal data I’d actually mind a company having, and I reached for the obvious answers: a password, a bank balance, a medical record. It took the best part of a year building an AI assistant to work out that the instinct is backwards. No single fact I fed it was ever the risk. The risk was what it could see once everything sat in one place, joined up, and that turns out to be true of a lot more than my own inbox.
WHAT IF YOUR CV WAS FIFTY PAGES LONG?
I was staring at my own CV next to a job spec last week, and it struck me how alike the two documents are — a few lines standing in for a whole person, matched against a few lines standing in for a whole role, like something out of a post-war job-queue office. That got me wondering: if the first reader of most CVs is now a model rather than a person, why are we still writing to fit one page?
EVERY 'NOT WORTH BUILDING' YOUR BUSINESS FILED IS NOW QUIETLY WRONG
My CRM had 4,223 duplicate company records rotting in it. Nobody had ever proposed cleaning it up properly, because ‘hire someone to manually review four thousand records’ was never going to win a budget conversation, so it sat there year after year, correctly filed as not worth the money. One afternoon and a script later it was done, and nobody had to make the case for it at all. The records hadn’t got any less duplicated. What changed was the price of fixing them, and that price change is bigger than it sounds.
THE BEST USE OF AI ISN'T DOING. IT'S DECIDING.
In the first week of my AI sabbatical I had the model open and ready to build, and I closed it again without writing a line of code. I spent that week arguing with it instead about what I actually wanted from the next six months. That conversation, not any of the tens of thousands of lines I went on to write afterwards, turned out to be the best use of AI I made all year. It’s also not the one most people reach for first.
DECISION DEBT: WHEN CAPTURE IS FREE, JUDGEMENT IS THE BOTTLENECK
I had more than 300 things sitting in my task list under a single heading, decide, and I’d never ruled on one of them. Writing an idea down used to cost enough effort that you only bothered if it mattered; now it costs nothing, and a heading called decide turned out to be a waiting room with no door. The debt was never the things I hadn’t done. It was the things with no action path at all — never ruled on, outside any system, running in my head instead of in a queue.
FORGET THE MODEL, LOOK AT THE HARNESS
Every day, without fail, something turns up in my inbox offering to solve my inbound pipeline problem. Same email, different sender, a hundred versions of the same idea: an AI that will take an entire function off my hands, starting Monday. Not one of the people sending them has the faintest idea what my pipeline actually looks like, and that’s the tell — they are all selling the model as if the model were the whole system. It isn’t. The model is the easy part. The harness around it — the context, the memory, the rules about what it is never allowed to decide on its own — is the actual work, and it’s where the real advantage sits.
IF A TREE FALLS IN THE FOREST
I write a lot of what I publish with help from AI now, this post included. Which raises an old question in a new form: if the thought is mine but the words are assembled by a machine, does the writing still count?
TWENTY YEARS OF FREE ADVERTISING FOR A PRODUCT WE NEVER BOUGHT
My mother kept flour and sugar in gallon Miracle Whip jars for twenty years, in a house that never once bought Miracle Whip. That is what reusable packaging does: it outlives the purchase and advertises for free. So why does UK retail sell everything in flimsy single-use packets at silly prices, and who is going to standardise the jar?
A DUTY TO REMEMBER, A RIGHT TO FORGET
I recently caught my own records lying to me, and it left me with a question I couldn’t put down: how much should any of us be in the business of never forgetting? A government has a duty to remember and a separate discipline about what it makes public. A person is not a government, and needs the right to forget. AI is quietly imposing the first on people who were only ever owed the second.