I started working almost immediately after my O-levels. I still remember buying The Straits Times at the LRT station, bringing it home, flipping through the recruitment pages, and looking for part-time jobs.

That was the traditional method. Buy the newspaper, take it home, turn to the recruitment pages at the back, and go down the columns looking for anything part-time. Nobody taught me this. I don’t remember who I would have asked. I just worked out that jobs were printed in the newspaper and the newspaper cost less than a dollar.

Then I’d pick up the landline and call the number in the advertisement and ask if they were still hiring.

I was seventeen. I’d just finished O levels. It doesn’t occur to me now to call a stranger and ask them for work, and I can’t fully account for why it occurred to me then. I didn’t know anything. I just wanted something and couldn’t think of a reason not to go and get it.

The first jobs were retail. Ladies’ fashion at Takashimaya, Robinsons, Metro, OG. Sales events at the Expo when they came up. Two in the afternoon until ten at night, on my feet the whole time. Serve customers. Unpack stock. Fold what people had unfolded. Wait. Go home. Five to ten dollars an hour. I’ve lost the exact figure.

Later I picked up a second job at the Kumon near my flat, marking worksheets for about five dollars an hour. The rate was worse, but it was ten minutes from home, so I took it.

I kept doing this through polytechnic and university. And somewhere in there I started keeping score.

How much am I worth per hour?

At that time, I think I was earning around $10 to $12 an hour. Later, I moved into badminton coaching and also took on private teaching, working more like a freelancer. My monthly take-home pay was quite good, although my CPF contribution was much lower than in a regular full-time job. Private coaching could easily bring in around $30 to $50 an hour, and for some sessions, even more. Suddenly, one hour of my time seemed to be worth much more than before. Or at least, that was how I measured it then. I remember feeling quite satisfied watching the number rise. It felt like progress, maybe even proof that I was becoming more valuable. But looking back now, I wonder if I was measuring the wrong thing.

I kept score like that for eighteen years.

Only recently did it occur to me that I might have been counting the wrong thing the whole time.

Was my value really an hourly rate?

When I was younger, the equation felt very simple. More skill meant a higher hourly rate, and a higher hourly rate meant I was becoming more valuable. So naturally, I wanted that number to keep going up.

But the older I get, the more I realise that work is rarely just an exchange of hours for money.

When someone hires us, they are not only paying for eight hours of our time.

They are also paying for our attention, energy, judgement, patience, creativity, experience, and our ability to solve problems. Sometimes, they are also taking up a bit of our emotional capacity.

And for certain jobs, the work does not really stop when the clock stops.

The body leaves, but the brain doesn’t.

A problem can follow you home. You can be eating dinner and suddenly think of a solution. You can be exercising and still replaying something that went wrong at work. Sometimes you even wake up with an idea.

Technically, nobody is paying you for those extra moments.

But mentally, work is still occupying part of you.

That is probably when I started questioning the idea of an hourly rate even more.

Maybe the real cost of work is not just the hours we spend doing it.

Maybe it is also the amount of space it takes up in our head.

If I solve something in 20 minutes, what am I being paid for?

This is something I think about quite often now.

Imagine I solve a problem in 20 minutes.

Maybe to someone else, it looks easy.

But perhaps it took me ten years of experience to know what to look for.

So am I being paid for the 20 minutes?

Or for the ten years it took me to make those 20 minutes possible?

That is a very different question.

Because if we only price work based on time, we may completely miss the value of experience.

The fastest person is not always doing less work.

Sometimes they simply paid for the answer earlier, through years of mistakes.

There’s a harder version of this that I’ve been avoiding.

Freelance coaching paid me more per hour than anything I’ve done since. Sixty dollars, no meetings, no politics, done when the session is done. By the logic I’d been using my whole adult life, that was the peak, and I should have built everything around it.

I went back into employment anyway. For Stability. For CPF, and for a salary that arrives when I’m sick, and for the kind of problems that take three months instead of one afternoon. Those were reasonable things to want. But they mean that at the exact moment I had the highest number I’d ever had, I traded it for something the number couldn’t see.

Which tells me I was never actually optimising for the hourly rate. I just thought I was, because it was the only figure I had. I don’t have a better one yet.

Then COVID happened

Before that, I had a fairly simple idea of what progress looked like. Work harder, learn more, earn more, watch the number go up. Keep moving. Most of the work I’d known growing up was also visible in a way that made this easy to believe. You went somewhere, you clocked in, you did the thing, you went home. The hours were the job. You could see them.

Then everything moved. Work went online, meetings went online, and businesses that had run on physical processes for twenty years had about six weeks to work out digital ones. Suddenly everyone was interested in automation, in systems, in whether anything could keep running when nobody was in the room. Technology had been doing this quietly for years, of course. COVID just pressed fast-forward.

Something shifted in me around then too, though I didn’t notice it happening. I stopped being interested in doing more work and started being interested in a different question: how do we make this run without adding more human hours to it? Instead of solving the same problem every week, could I build something that solved it once? Could a workflow lose three steps nobody needed? Could information move on its own instead of waiting for someone to forward it? Could a thing keep working after I stopped watching it?

That’s roughly when my relationship with work changed. I went from asking how much I was worth per hour to asking what I could actually produce in one. Those sound like the same question. I don’t think they are.

AI has pushed it further. Something that used to take an afternoon, for example, building a working website from scratch, can take half an hour now if you know what you’re doing. Writing, research, analysis, admin, and increasingly parts of the deciding itself.

So if I do in thirty minutes what used to take three hours, is the work worth less because it took less time?

That can’t be right. If anything, it’s the reverse. The value has moved into knowing what to ask for, what to check, and what not to trust. AI will produce an answer without much hesitation. Somebody still has to know whether the answer is any good or it’s even true. A workflow can be automated by more or less anyone now. Understanding the problem well enough to know what should be automated is a different skill, and it hasn’t gotten any cheaper.

Which makes my old scorekeeping look even worse. How much I’m worth per hour was always a question about how long I take. It never once asked what I was actually producing while I took it.

But there’s a part of this I keep walking around rather than through.

Say I build something that removes eleven hours of work a week. Not hypothetically. That’s roughly the shape of the last thing I built. Those eleven hours don’t come back to me. They go into the week, and the week absorbs them, and something else fills the space. The saving is real, and it is permanent, and it belongs to the organisation, which is the arrangement now, and I understood the arrangement.

I suddenly remembered something someone once told me: JOB means “Just Over Broke.”
I used to laugh at it because it sounded like one of those dramatic lines people use to sell entrepreneurship. But the older I get, the more I understand why it sticks. A salary can keep life stable, but if it is my only source of income, I am still heavily dependent on continuing to work for the next one. My salary remains largely unchanged, perhaps increasing slightly over time due to inflation adjustments and the organisation’s goodwill. It was calculated before the system existed, and it’ll be recalculated on a schedule that has nothing to do with it.

So the productivity question turns out to be the ownership question wearing different clothes. It was never really Is my work worth less now that it takes less time. It was when the tools make one person do the work of three, who ends up holding the difference?

I don’t think there’s a clean answer. I do think it’s a better question than the one I was asking at seventeen with a newspaper and a landline, and I notice that almost everything written about AI and productivity stops carefully short of it.