AI is an extension of me in a machine.
I was three iterations deep into a comic strip, watching Gemini put a collar on a character who’d never had a collar in any version, when I realised I was looking at the same problem I’d spent five articles describing in organisations with thousands of people. Style drift. Definition of done gone soft. The same dysfunction, just compressed down to one person, one laptop, one Friday afternoon.
The difference was what happened next. I didn’t need a steering committee. I didn’t need to wait for a financial threshold to clear or a board paper to go in three weeks ahead of a meeting. I just changed the prompt and tried again.
That’s the thing about working at the scale of one. There’s nobody between me and the outcome. No middle layer, no Chinese whispers carrying my intent through three other people before it reaches the work. If the comic strip doesn’t look right, that’s mine to fix, immediately, and there’s a kind of clarity in that, a clean line from decision to consequence that almost never existed in any of the organisations I spent thirty years inside. The same problem that took Stats NZ years to half-resolve, Scrum or Kanban, which method actually fits the work, I can resolve for myself in an afternoon, because I’m the only one who has to agree with the answer.
It can be a lonely way to work, though, and I won’t pretend otherwise. So I’ve built something to sit in that gap. I’ve put an About Me file into Claude, my taste, my voice, the way I actually think, so that what comes back has a chance of sounding like me rather than like the four thousandth LinkedIn post on the same subject. I use other platforms differently, for research, for testing an idea from another angle, for seeing whether a thought holds up when something with a different bias pushes back on it. It’s a handful of different counsel rather than one tool, each one good at a different part of the job, closer to how I used to work inside an organisation than people might expect. I just don’t need an org chart to do it anymore.
The voice-to-text side of this has surprised me more than anything else.
For most of my life, I wrote the way I’d been taught to, type it, read it back, correct it, type some more. Mind maps. Handwritten notes. Bullet points I’d later try to expand into sentences. It worked, in the sense that things got written, but it never quite captured how I actually think, because how I actually think doesn’t arrive in tidy bullet points. It arrives the way I talk, in long connected runs, one idea pulling the next one behind it.
I’d tried voice-to-text before, years ago, and it never worked for someone like me. English is my third language, after Cantonese and Bahasa Malaysia, and I don’t sound British or American, and the older speech recognition tools simply couldn’t hear me properly. Wrong words, wrong spelling, wrong context, dictation that fought my accent instead of capturing it. I gave up on it more than once.
Wispr Flow is the first one that actually heard me. It captures the nuance, the pronunciation, the pace, and somewhere in using it I came across Zinsser’s Writing to Learn, which gave me the missing piece, the idea that thinking happens in the act of saying something out loud, not after it, and that stopping to fix a sentence halfway through is stopping the thought itself. Once I let that go, once I let myself talk fast when the idea was exciting and trust that it would be captured properly, the writing changed. All five articles before this one came out of that process, voice first, structure after. I don’t think I’d have written any of them the way I did, ten years ago, with the tools that existed then.
So when people ask me what I actually think AI is, after trying most of the major platforms over the past couple of years, ChatGPT, Perplexity, Gemini, Claude, Deepseek, Manus, Grok, after the courses, the prompt engineering, the experiments that went nowhere, here’s the honest answer.
It’s still a bicycle. That part hasn’t changed since I first wrote it. You learn the rules of the road, the etiquette, what it’s good for and what it isn’t, and once you know how to ride it, it gets you from one place to another faster than walking, without doing the walking for you. I’m not dependent on it. I’m faster because of it.
What’s changed is what I think the bicycle is actually carrying.
It feels less like a personal assistant now and more like an extension of my own thinking, put into a machine that can hold a version of my taste, my voice, my judgement, and reflect it back to me in different forms, depending on what I need that day. Gemini draws in something close to my comic style. Claude drafts in something close to my voice. The research tools dig into a topic the way I would, if I had the hours to do it myself. Each one is carrying a piece of how I think, and I’m the one deciding what to do with what comes back. None of them is me.
There’s a newer part to this that wasn’t here when I started the series. Some of the counsel runs on its own now, on a schedule I set once and mostly leave alone. Every week a report on my finances arrives without me asking for it, the numbers pulled together, the movements flagged, the few things I’d actually want to look at sitting near the top. Every week the same happens for the Pipitea Mews Body Corporate Committee I sit on, the updates gathered and drafted so I meet the BC Manager already knowing what has changed, instead of finding out halfway through the meeting like everyone else. I read them, I decide what matters, I act or I don’t. But the fetching and the first draft were done before I sat down, and that used to be somebody’s whole job.
That’s the part I didn’t quite see coming. At the scale of one, I’d assumed the recurring work, the weekly rhythm a team used to carry, would either land back on me or simply not get done. It turns out a good deal of it can be handed over and checked rather than done from scratch, which is closer to working with a capable team than anything I expected to find on my own. The machine doesn’t decide what the numbers mean. It doesn’t sit in the committee. It does the gathering and the first pass, the way a junior analyst would, and it leaves the judgement where it has to stay, with me.
That’s the part the bicycle metaphor still gets right, even now. The bicycle doesn’t choose the destination. I do. It just makes the distance shorter, and it means the journey doesn’t have to be lonely the way I once worried it might be in retirement, no office, no team, no water cooler. I find I’m more connected now than I was for a lot of my working life, because I can take an idea, set it down, walk away from it, come back later with something new to add, and the thinking is still there waiting, sharper than it would have been if I’d had to hold the whole thing in my head the entire time.
Looking back across everything in this series, the pattern holds at every scale I looked at it. AI won’t remove ANZ’s production bottleneck. It won’t dissolve Stats NZ’s immunity system or smooth over the gap between a steering committee report and what was actually happening on the ground. It won’t move Te Pūkenga’s funding any faster, and it can’t read a room the way thirty years of watching people abandon ship taught me to. None of that changed because the scale dropped from an organisation of thousands down to one retired man and his laptop. What changed is that at this scale, I’m the only constraint left to find, and most days, I’m also the one who gets to fix it.
I think that’s the real difference age and experience buy you. Not certainty, I don’t have much more of that than I did at thirty. But I’ve seen enough versions of the same mistake, in enough organisations, that I recognise it faster now, in myself, in a prompt that isn’t working, in a strip that needs a sixth pass before the collar disappears. AI hasn’t replaced that. If anything, it’s given me more places to practise it.
My daughter grew up mostly hearing titles. Project Manager. CIO. Senior Manager. Platform Engineering Director, toward the end, a title I’m not sure she ever fully understood, and honestly, neither did most people I worked with. None of those titles ever told her what the work actually was.
What I’d want her to know, more than any of it, is that the work was always about the people in the room, not the tool on the desk. That was true with Scrum. It was true with cloud migrations and steering committees and budgets stuck above someone’s financial delegation. It’s still true now, with AI sitting on my desk instead of a project plan. The tool changes what’s possible. It has never once changed what actually matters, which is whether you can read the people around you honestly, and whether you treat them well while you do it.
This website was never meant to be a memoir. I’d like her to read it one day, not for the organisations or the job titles, but to see how her father learned to work with what he was given, with enough discipline to keep going and enough humility to know when to change course. If she takes one thing from it, I hope it’s this: learn from the people who went before you, take their mistakes as your own lessons, and you’ll fumble less than I did.
AI makes that easier now than it’s ever been. It gives you a faster bicycle to go find out what you actually believe. It doesn’t do the believing for you.
I’m still riding mine.