Singapore Just Showed Us Which Jobs Are Dying (The Middle Trap)

Why anybody pays you

I run a team of about ten, so every bad hire hurts our culture and our finances. Over the last two years, what I look for has quietly changed. I never announced it, and I doubt other bosses have either. Let me show you the mechanism.

Start from first principles. Companies do not pay you for hours or for a degree. They pay you to make a problem go away. There are really only three ways a person does that:

What Waze did to the taxi uncle

Fifteen years ago a KL taxi uncle was gold. He knew every shortcut, every road that jams at 6pm, which flyover to avoid in the rain. That mental map took him 15 years to build, and you paid for it.

Then Waze arrived. His knowledge did not become wrong. It became free. He did not get worse at his job. His advantage was copied and handed to a 19-year-old on their first day driving Grab.

That is what is happening to the experience bucket across every desk job you can think of. Nobody sent a memo.

Singapore's numbers, read closely

In the second quarter of this year, about 4,500 people were retrenched in Singapore, the highest quarterly figure since the end of 2020, up from 3,800 the quarter before, mostly in tech and manufacturing. Yet unemployment sits around 2%, more companies plan to hire than to cut, and the headlines say the economy is fine. Which is exactly why it is worth looking closer.

In July, Singapore's government technology agency cut 93 people. A tiny number that barely made the news. Then on 4 August a minister gave Parliament a breakdown: 42% of those cut were in their 40s. You might think the headline is older workers being hit hardest. But she said the 40 to 49 group was not over-represented. It matched their share of the workforce.

That sounds like fairness. It is actually some of the worst news in the story. The old deal your parents worked under was simple: put in the years and you become harder to remove. Years were your armour. If you are cut at exactly the same rate as someone who joined last year, your 20 years added nothing to your protection. One more detail: those let go had been there 5.4 years on average, those kept about 6. Tenure did not decide it. Something else did.

The young are fine there. The middle is cracking.

Everyone says AI is taking entry-level jobs. In the US there is real data on that: employment for 22 to 25 year olds in the most AI-exposed jobs has fallen. But in Singapore, around nine in ten recent public university graduates found work within a year, in line with previous years. The young are fine. The middle is cracking.

Malaysia has the opposite disease. Our graduates do find jobs; they just do not find jobs that use their degree. The Human Resources Minister told Parliament in July that 1.6 million graduates work below their qualification, about one in three. We cover it in our research on the underemployment paradox.

So in Singapore the middle is being squeezed, and in Malaysia the bottom never lifted off. Different problems, same root: people are no longer paid for what they know. They are paid for what they can decide.

Watch where the money goes

If you want to know what a government really believes, ignore the speeches and follow the money. Singapore has put serious money into retraining people over 40: up to 90% off course fees and up to S$3,000 a month in your hand while you retrain. Three thousand a month to go back and learn. No government pays for a problem that is already solved. You only pay for one you can see coming. They looked at the workforce, saw which floor was about to give way, and started building a net under it.

Now ask the uncomfortable version: who is building that net for you? In Malaysia, be honest. There is no cheque with your name on it and no RM3,000 a month while you figure things out. I am not complaining or asking for sympathy. I want you to see the map you are standing on, which means you have to build the net yourself. In Singapore the state funds upskilling. In Malaysia you have to find your own way, with or without the money, and it is very doable. Our guide to how to upskill for AI is a starting point.

The middle trap

There is a floor in every career where you are too expensive to be cheap hands and too easy to copy to be rare. I call it the middle trap. The worst part is that you do not feel it while you are in it. It feels comfortable, because comfortable is what the trap feels like from the inside.

This is also why the 25 year old should care. The habits that lead to the trap, doing the same well-understood work year after year and never owning a decision, start early and feel safe. The habits that avoid it, taking on ambiguous problems, making calls and learning tools that multiply you, also start early.

Run this test tonight

Write down the last few things you did at work. Next to each, write yes or no to one question: could a smart stranger with the right tools do this in one afternoon? Every yes is something you are paid for that a newcomer with AI could copy.

Then find the one thing on that list where you actually had to decide something. Go and do more of that. That is the job now, and it will be even more the job next year.

If your list is mostly yeses, the fastest way out is a skill that lets you build and decide, not just execute. Learning to build software with AI is one of the most direct routes, because it turns you from the person who knows the process into the person who redesigns it. You can test whether it suits you with our free trial, or read about jobs AI can't replace first.