Category: Small Simple Steps

I was fixing a comic strip for one of my articles when the notice turned up. Microsoft is retiring Whiteboard for personal accounts. No new boards after 22 August 2026, and if I want to keep anything I’ve already made, I have until 5 September to export it before it’s gone for good. So here I am on a weeknight, opening board after board, saving each one to PDF and image files before the door shuts.

Let me say the ridiculous part plainly, because it’s true. I love this app. I have loved it since it first appeared. It has been my scribbling pad, my drawing surface, my think-out-loud board, the most useful all-round tool I’ve put my hands on in years. When I needed to sketch an idea, rough out a diagram, lay out a comic strip panel by panel, or just make a mess on a big blank space and see what fell out of my head, this is where I went. Grown men are not supposed to grieve software. I seem to be doing it anyway.

These days the board is where a lot of my thinking starts. Before an article becomes words, it’s usually a mess of boxes and arrows on a canvas, ideas pinned up where I can shove them around and argue with myself until an order finally emerges. The comic strip I was mending when the notice appeared was sitting on there too. So the retirement takes more than a drawing app off me. It takes a room I think in.

And yet, sitting here exporting, I notice I’m not angry, and I’m not even surprised. It looks like a loss, and it would read like one if I saw time as a straight line where the things I rely on are supposed to stay put and wait for me. I’ve come to see it differently. This is not the first tool I’ve had to pack up and carry off someone else’s platform, and it won’t be the last. Across nearly forty years of work, through banks in Kuala Lumpur and Amsterdam and government agencies in Wellington, I have watched the systems I depended on get switched off, deprecated, replaced, and merged into something new with a worse layout, over and over. I still remember the first time a platform I trusted was pulled out from under a team I ran, and the useless meeting where we all pretended the replacement was an upgrade. What I’m doing tonight, I’ve done many times. The notice isn’t a crack in the world. It’s a season turning, and I happen to be standing in the yard when the weather shifts.

Whose house it was

Here’s the first thing worth being honest about. The whiteboarding itself isn’t disappearing. Microsoft is folding the capability into Loop and Teams, so the ability to draw on a shared board lives on inside other products. What retires is the standalone app I grew fluent in, the particular room I worked in, while the furniture gets carried off to buildings I don’t visit. The function survives. The home I knew for it does not.

Which brings me to the thing I got wrong for years without noticing. My boards lived on Microsoft’s servers, and somewhere along the way I started treating that as mine. It felt like a home. It was a rented plot on someone else’s land, and the export deadline is the letter reminding me whose name is on the title. I never owned the board. I rented a spot, paid nothing for it, grew comfortable in the rhythm, and mistook the comfort for ownership. That is the quiet trick of permanence. We rent it on someone else’s cycle, settle in, and forget we don’t hold the deed, right up until the landlord sends notice.

The deadline is doing something else too, something I only half enjoy. It is teaching me, and it is charging tuition in my own hours. Nobody is forcing me to save these boards. If I let the date slide past, the work simply vanishes, and no one but me will ever notice it’s gone. So I sit here, export by export, paying for the lesson with an evening I won’t get back. The retirement notice taught me nothing. The exporting is doing the teaching.

I notice, too, what the export actually does to the thing I’m saving. A board inside the app is alive. I can move a box, redraw an arrow, wipe a corner and change my mind, come back next week and keep going. The moment I save it to PDF, it stops being a place I work and becomes a picture of a place I used to work. The living surface flattens into a keepsake. That, in the end, is what keeping usually amounts to. We can’t hold on to a thing while it’s still moving, so we hold on to a still image of it and call that a memory. The boards I’m rescuing tonight will survive as pictures. Not one of them will ever be drawn on again.

Then there is the cost people underestimate when they talk about switching tools, as if moving were only a matter of matching a feature list. The real cost is fluency. I didn’t just use Whiteboard, I became fluent in it. I knew without thinking where every control sat, how it behaved, what it would let me get away with when I was working fast. Moving to something else means learning a new grammar with my hands all over again, being clumsy for a while, being slow before I’m quick. That re-learning is the tax, and I’ve paid it before in far bigger denominations than a drawing app.

The bigger version

I know that cost because I’ve lived a larger version of it. My own role ended in November 2024. I was made redundant, and I stepped from there into early retirement. Here is the honest wrinkle. I was ready for the retirement. I was not ready for the shove that started it. Being prepared for the destination is not the same as being prepared for the hand in your back that sends you there ahead of schedule. One of those I had planned for over years. The other arrived on someone else’s timetable, decided on someone else’s ledger, and handed to me as a fact I had no vote in.

I won’t dress that up into more than it was, and I won’t pretend it was only a line in a budget either. The same ache turns up wherever something with a rhythm ends, whether it’s a tool you loved, a job you were good at, a house you lived in for twenty years, or someone you kept close. I’ll leave that there. You can put your own face to it more accurately than I can put mine.

What I carried out of it is the same thing I’m carrying out of this small evening of exporting. The capability walked out of the building with me. Whatever made me useful was portable, even after the reason for keeping me around got closed off on an account I never controlled. From inside the notice, renewal looks like a tragedy. Step back, and it’s the cycle doing what cycles do, turning, and carrying the value that actually mattered into whatever comes next.

Keeping exit costs low

Two things this is not. It isn’t a call to nostalgia, and it isn’t a call to hoard every tool you’ve ever touched. If I tried to own everything, host all of it myself, keep a private copy of half the internet in a cupboard, I’d drown in my own caution, and I’d deserve it. The useful move is smaller than that. Keep your exit costs low.

That’s why I run my own WordPress on my own hosting rather than writing inside someone’s walled app where my words are a guest. It’s why I build network storage out of old machines that were headed for landfill, and keep my own copies of the things that matter to me. It’s why, when I make something I care about, I keep it in a format I can carry off the platform on the day the platform decides it no longer wants to host me. Not because I distrust every vendor, that way lies paranoia, but because I’ve read enough of these notices to know the ground you stand on belongs to whoever can send you one. Every notice like tonight’s is tuition for the same lesson about who controls that ground. I’ve decided to keep learning it cheaply, in advance, on my own terms, instead of expensively, in a hurry, on theirs.

So I’ll finish exporting the boards. I’ll be clumsy in whatever I use next, for a while, until my hands learn the new room. Nothing I rely on is forever, and I’ve made my peace with that, one export at a time.

[Editor’s update, 23 August 2026: Microsoft has since moved the dates. Whiteboard for personal accounts now goes read-only on 22 September 2026 and retires on 16 October 2026, a little more runway than the first notice gave. I didn’t wait for it. I’ve exported every board and deleted the .whiteboard files myself, on my own schedule instead of theirs.]

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.

For 4 years those boxes sat in the closet, the filing cabinets, the shelf in the corner, and I never once opened them. I moved to Hamilton in 2022 and the paper came with me, taped up, labelled, promising to be useful one day. Now I’m moving house again in 3 weeks, so I finally cut the tape. Most of what I found was printouts. Articles from Harvard Business Review, research notes from Gartner and Forrester, journal pieces, newsletters, things I printed off before AI, before the internet was much use, and a fair bit of it from before the internet at all. I printed them because that’s what you did. You couldn’t read a Gartner report on your phone on the train back then, so you printed it, folded it into your bag, and read it on the commute, or in a meeting where you looked busy and were, occasionally, actually learning something.

People talk about hoarding as retail therapy, and I understand the pull of it: buying things with your own hard-earned money is a small hit of happiness, and there’s nothing wrong with that. My hoarding was a different animal. Mine was knowledge. Over 30-odd years across Southern Bank, ABN AMRO, the National Bank/ANZ, Inland Revenue, Stats NZ, I gathered paper the way other people gather shoes, because in my line of work the paper was the point. It was the raw material of doing the job well. So I kept it, and kept it, and moved it from house to house, and told myself I’d use it again one day.

The maybe bucket is a trap

So I did what you’re supposed to do. Three buckets. Keep, throw, and maybe. The keep pile is easy and the throw pile is easy. The maybe pile is where good decluttering quietly goes to die.

I read something years ago about the maybe bucket that stuck with me, and it turns out to be true every single time. The maybe bucket is not a decision. It’s a holding pen for your own uncertainty. You put a thing in there because you can’t decide, and when you come back to look at it again, you are exactly as undecided as you were the first time, so it lives forever. Never filter the maybe bucket. The moment you start sorting it, picking through it a second time, you’ve handed your uncertainty a way to keep everything.

My rule is blunter than the books make it sound. Hell yes, I keep it. Hell no, it’s gone. And maybe is hell no, because the hesitation is the answer. If I have to think about it, I already know. Then I run one test on the whole lot: would I miss this a month from now, 2 months from now? These boxes have been sealed in a closet for 4 years and I haven’t missed a single page. So the answer writes itself. Would I use it again? Probably not. Would I ever find it again if I wanted it, buried in a box, filed under a system I set up a decade ago and have long forgotten? No. You never find the thing you archived by hand. And if I genuinely want the idea back, well, you’ve got AI now. You’ll remember you once read it, you’ll ask, and it will hand you a better version than the yellowing page you were clinging to.

Knowledge got cheap

Here’s the thing that landed on me somewhere in the middle of the second filing cabinet, kneeling on the floor with a bin bag. Knowledge is cheap now.

When I started out at 19, people paid for what you knew. You acquired it, you studied it, you carried it around, and that accumulation was your edge. It was why you got hired, why you got promoted, why someone senior asked for your read on a problem. I made CIO at ABN AMRO in my early thirties, and a good chunk of what got me there was simply that I’d done the reading nobody else had bothered to do. The paper in my bag was professional capital. It had a price, and I’d paid it, in commutes and late nights and subscription fees.

Now anyone can Google it. Better than that, they can ask an AI to do the deep dive and explain it back at whatever level suits them, like they’re 5 years old, or like they’re a corporate executive, or like they’re a CIO who needs it in the language of a board paper. The thing that took me years to gather, a curious teenager can now summon in a sentence, in better shape than I ever kept it. That paper mountain in my closet, the one that was capital once, is recycling now. I’m not being dramatic about it. I’m literally putting it in the recycling.

What I couldn’t throw out

And yet I kept some of it. Not much, but some.

I kept my own notes. The newsletters I wrote, the journals of my own thinking, the observations I jotted down over the years that were never online and never will be. That’s not knowledge I can Google, because nobody has published it, including me. It’s mine, and I keep it because it feeds what I write now on Strategic Kata. The rest, the borrowed knowledge, the reprints of other people’s cleverness, I let go, because the internet holds a better copy than my cabinet ever did.

My wife ran the same test faster than I did. She had the course materials from her Cafe Service Level 2 Certification and her Certificate in Dental Assisting from the New Zealand Dental Association. I asked if she wanted to keep them. She said, give me some time. Less than an hour later she came back and said, chuck it out, I’m not working anymore, and the information’s probably dated by now anyway. Then she said the thing that is the whole point of this piece, without meaning to say anything profound at all: the rest is in my head. The course materials went in the no bucket. The certificates she kept. The knowledge stayed exactly where it had always lived.

The information was the cheap part all along. What held its value was what we did with it, and what stayed in our heads after the paper was filed and forgotten. AI didn’t take that from anyone. It just made it obvious, by making the information itself free. The stuff that’s still worth something is the stuff that was never really on the page: the judgment, the pattern recognition, the scar tissue from having been in the room when it went wrong.

Books are where my rule breaks, and I’ll admit it plainly. I can’t part with physical books. I have a hardcover of Management Control Systems, 9th edition, Anthony and Govindarajan, from my MBA days. I read it front to back and went back to it for years. The information in it is dated now too, of course it is. That’s not why I keep it. I keep it for the earmarks, the notes crammed in the margins, the sticky tabs, the yellowing pages, the whole record of me arguing with the author across the page. Master that book and you know what to look at and what to consider, and the rest is delegation. What I value there isn’t the content. It’s the layer of my own thinking sitting on top of it, and you can’t print that off Gartner.

One room at a time

Then there’s the rest of it. The extra furniture nobody sits on, the kitchen appliances we bought and used twice and left to gather dust. There’s a quiet lesson in an appliance you haven’t touched in a year. I’m a minimalist by nature, and my wife is learning to be one, though it’s taken her time and a few house moves to get there.

We’ve got 3 weeks, so we’re doing one room at a time. AI handled the checklist and the paperwork, which used to eat a weekend on its own. Thinking about it, this move is the least stressful we’ve had, and the reason is simple: we’re both home full time now. The hard moves were the ones where we both worked, packing at midnight, arguing about who booked the truck. This time we can sit on the floor with a box of old crockery and utensils and stuff we’d forgotten we owned, and talk, and laugh about where it came from. Sentimental value? Plenty. Worth keeping? Not really. So it’s sold, or given to someone who’ll use it, or dropped at the Salvation Army or the op shop.

The lawn mower and the trimmer are the last things to go, and they can’t go yet. I’ve still got to mow and trim the lawn one last time before I hand the keys back to the property manager, so those two stay until the tenancy exit is done. Small mercy on the other end: the place we’re moving to has no lawn to mow at all.

We upsized once. We downsized once. Now we downsize again. Life is good.

I’ve been drawing the same characters for a few years. Bald heads, no gender, no mouths, just eyes and noses. They live inside my previous Small Simple Steps blog, mostly as cover images. One of them is sitting inside a giant jar saying “I’m stuck.” A voice from outside says: “You’re not a tree. Get moving.”

Dry humor, organisational observations, leadership absurdities. That’s the strip.

The ideas are never the problem. I have 10 to 20 of them sitting on paper right now, thumbnails and notes, waiting to become strips. A professor explaining that innovation is Q+A (questioning plus action), then being asked what Q minus A is. “That’s philosophy,” he says. A person standing outside the box, being told to think outside the box, while a voice from above is also being told to think outside the box. The joke writes itself. Drawing it takes time.

Microsoft Whiteboard, Microsoft Paint, adjusting angles, getting expressions right when your characters don’t even have mouths. That’s hours per strip, sometimes more. So the backlog stays a backlog.

A few weeks ago I uploaded a series of my strips to Gemini and asked it a simple question: what do you need from me to draw in this style? After a few rounds of feedback and iteration, it rendered a 3-panel strip that looked exactly like mine. Same characters, same sparse style. It had added mouths. I told it to remove them. The next render was right.

Then the next one had mouths again. And collars. And shirt buttons on a character that wears nothing but eyes and a nose.

Gemini forgets. It drifts back toward its training data, toward what it expects a character to look like, and I have to reload my source strips and re-edit the prompt to pull it back. A strip I’m happy enough to publish takes 5 to 6 iterations on average.

I want to be honest about that number. It’s still faster than building the same panel in Microsoft Paint. And Gemini can reframe a panel’s composition quickly, repositioning objects, adjusting angles, based on how I describe what I want. The back-and-forth is productive.

That’s the experiment. Here’s what it means.

The production gap closed. The 10 to 20 ideas on paper now have a path to 10 to 20 strips. The thinking part, the theme, the dry humor, the character dialogue, the punchline, none of that came from Gemini. That part is still mine. What Gemini removed was the rendering work sitting between the idea and the finished image.

But I noticed something else worth naming. Gemini is a good imitator. Feed it a consistent style, it replicates the style. I’ve seen someone on LinkedIn feed a child’s dinosaur drawing into the same kind of tool. The output was detailed, cinematic, the kind of thing you’d see in a film. The AI had extrapolated past the source material into its own idea of what a dinosaur should look like. The child’s version disappeared.

That’s a different thing from what I did. My strips have a consistent style. Gemini stayed inside it, mostly, with reminding. But if the source material had problems baked into it, the output would have reproduced those problems faithfully, and faster.

Apply that to an organisation. Feed AI your broken processes, you get faster broken processes. The tool doesn’t audit what you give it. It amplifies it. Garbage in, garbage out, just at a speed that makes the garbage harder to spot.

I want to be honest about something else. Drawing is meditative for me. The slow process of sketching a bald character, finding the right angle, sometimes realising mid-sketch that the idea needs sharpening, that’s part of how the strip develops. I’m not giving that up. The hand-drawn ones will still happen.

But when the idea is clear, the message is ready, and the only thing left is hours of rendering work, that’s where Gemini earns its place. A bicycle. I still have to steer, and apparently I have to keep reminding it that my characters don’t have mouths.

The production bottleneck is the real constraint in most creative work, the gap between having an idea and having something to show for it. If AI closes that gap without touching the thinking, the thinking gets more time. That’s the trade I keep coming back to.

Just make sure what you’re feeding it is worth amplifying.

I have 10 to 20 strips waiting. I’ll let you know how many survive the experiment.