Now in their 30s, millennials risk becoming the people we used to judge

Not all coming of ages are good.

DISCLAIMER: THIS IS A SUBSTACK-EXCLUSIVE ARTICLE BROUGHT TO YOU BY THE WOKE SALARYMAN.

I used to call all the drivers ‘uncle’ when I took my Grab rides.

But now that I’m in my mid 30s, I’ve been a lot more careful about who I call ‘uncle’. After all, some of these ‘uncles’ are about the same age as me.

Recently, on at least five of such Grab rides, I heard the same theory from them. It goes something like this: Once you turn 40, the workforce is more or less done with you. This is particularly true if you haven’t done anything exceptional with your career.

In your 40s, you should be about to sunset the corporate work environment, and start to prepare for a life as a private-hire driver.

Of course, this is nothing particularly new. It’s called ageism in the workplace, and now that millennials are entering (or have entered) our 40s, it’s beginning to hit us.

If that sounds terrifying, that’s because it is. It’s a long time between your 40s and 65 — when your CPF Life payouts actually start. Unless you saved and invested diligently during your early working years, you’re in for a rude shock.

Incidentally, your 40s is also when larger expenses start to kick in. Think: your kids’ education, parents’ medical expenses, caretaking costs, etc.

(PS: If you think 40 is old, in Indonesia you’re ‘old’ when you turn 30.)

Millennials now risk becoming the people we disliked

Remember that over-40 senior colleague you had at work that you disliked because they clung on to their position at all costs?

The one that simply refused to retire or move on?

Now that millennials are finally on the receiving end of ageism, it’s easy to see why they did so.

If you’re basically unhireable at 40, it makes sense to guard your existing role with all the ferocity you can muster. Even if you’re no longer growing or learning or even contributing.

(We saw this last year with the job-hugging trend, and we’ll definitely see more of it in 2026 with the state of the job market.)

And of course, when that happens it’s a lose-lose situation.

You give up career growth for a stable but stagnant career, and your younger colleagues start to feel the frustration.

Instead of rising up to become, say, a director, they’re stuck in mid- or entry-level positions. Years pass, wages don’t go up significantly, younger folks are priced out of housing. They delay plans to have children indefinitely. Or simply give up on them.

A whole generation of lost potential and fresh ideas, slowly stagnating and decomposing in mid-level drudgery.

Millennials have been there. And if we don’t do anything about it, Gen Z will too.

What’s the solution?

I think there are two parts to this puzzle that are — as with most things — easier said than done.

The first is a mindset shift among employers (and yes, employees too) towards how people post-40 can still contribute to society.

In other words, we need to stop hiring exclusively young people.

When we show that people still participate in the workforce in their 40s, 50s, or even 60s, we create the psychological safety for people to give up their leadership positions for young blood.

Without this psychological safety, nothing will change.

Of course, this won’t be easy.

We’ll need to manage thorny generational differences (and egos) in a multigenerational workplace. Not to mention decouple the expectation of higher age = high salary. Or age = authority.

(Which could be challenging for those with more Confucian or traditional beliefs.)

The second half of the puzzle is something we’ve been talking about for years: Financial literacy.

If senior workers can achieve financial security at an earlier age, I believe they’d find stepping away from high-paying, high-stress roles easier.

Instead of seeing these roles as terminal career stops to extract as much salaries as possible from, they could have the freedom to reskill into something that ironically makes them more valuable in the long term.

How does that happen? It starts with being more conscientious on what you spend on. Buying a house within your means. Downgrading from the car when you no longer need it. And of course, investing for the long term. And not being scammed.

All the other stuff we regularly talk about on this page.

A parting thought:

A system that lets seniors step aside safely isn’t different from the same system that lets you move up sooner.

In fact, it’s the same system.

Keeping experience in the room saves you from repeating expensive mistakes.

If we accept “unhireable at 40”, the line will creep to 35.

Ageism doesn’t just punish the old. It builds a workplace where no one is allowed to age with dignity, then sells that fear back to the young as “hunger”.

Till we fix both, no amount of anti-discrimination advertising will make a difference.

Stay woke, salaryman.

What we foresee in the comments section

“This piece assumes everyone can just ‘save early’ or ‘buy within their means’. Not everyone has your income or luck.”

Fair point. Not everyone has the same starting line. The piece isn’t meant to guilt those struggling, but to highlight what happens when none of us prepare. Ageism hits hardest when people are financially cornered. Systemic inequality is real, but so is the personal need to defend yourself against it. Both truths can and do coexist.

“You’re framing ageism as a personal finance issue when it’s really structural.”

Completely agree that ageism is structural. But waiting for structures to change doesn’t pay the bills. Financial literacy isn’t the solution, but it’s more of a defensive tool. The ideal is policy reform and societal awakening; the practical step is personal resilience until we get there. We all can do things that help us get there faster.

“You only care now that it affects you. Gen X has been dealing with this for years.”

The point isn’t that millennials discovered it, but that it’s our turn in the cycle. Every generation thinks they’ll escape the same traps until the system catches up. Recognising that pattern is the first step to breaking it.

“By saying older workers should retire gracefully, you’re validating a system that discards people once they’re not ‘hungry’ enough.”

The goal isn’t to protect the system. It’s to reduce fear. When people know they can leave without losing dignity or security, the system has less power to exploit them. The idea of “stepping aside” isn’t submission; it’s reclaiming choice from a rigged game.

“Many seniors want to keep working because they need purpose, not just income.”

That’s fair. Purpose matters as much as pay. Btw “stepping aside” doesn’t necessarily mean “disappearing”. It means moving into roles where experience is valued differently. Mentoring, part-time work, new fields, etc. People should have the option to stay or to go, not be forced either way.

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