Late 30s and Still Rejected: The Harsh Reality of Upskilling in Singapore

[Eliwood]

Recent years I noticed a lot of age 30+ guys who speak good english driving grab. Anyone who takes grab a lot should have noticed that. Though it's nothing to be ashamed of, I believe true blue sg men with education should not be doing these gig jobs.

Usually it is by choice.

Or they got attitude problem...

 

[mcylo]

Ts, did u vote for Tan See Leng?

 

[hctawsgs]

63% in CCK voted for Traitor Tan, so mai kpkb.

 

[shock]

Late 30s is consider too old.

 

[kimsix]

Is like the matrix, there are those who are trapped unknowingly, and there are those who are trapped...knowingly, and there are those who assist the powers that may be, to perpetrate the lies.

And of course, there are those who are out of the matrix and see things for what they truly are.

It is going to get worse in next 5 years. wana bet kkj, our population going to hit 6.66m by 2030 ? another 600K mouths coming to crowd every space we have.

pap will act blur and tell you 65% wanted this. pap is "making best effort" to slow down population growth....but 6.66m is bare minimum needed to keep sinkapore prospering.... no need chatgpt to make this PR speech..

prosperous FOR WHO? sinkies never ask.

 

[MaskedRider555]

dun talk...take action

 

[IAmZTX]

you are upskilling and no relevant experience. Expecting the same salary as you get before? Its impossible. Time to rethink about your salary expectation.

Fresh graduate, no experience (20s) vs late 30s with no relevant experience.

Doesn't mean you take X number of courses or certification means employer must employ you. Any tom dick and harry can do this too.

End of the day, it depends on your working experience.

 

[LoneTraveller]

I’m writing this because I need to be honest about something that’s been weighing on me for a while.


A few years ago, I bought into the dream that upskilling would change my life. I signed up for project management modules, took data analytics courses, and spent countless evenings and weekends learning new things. I genuinely believed that if I worked hard enough, if I kept improving myself, I’d eventually land a better job or maybe even start a new career.


But now, after sending out hundreds of job applications—each one painstakingly customised, every cover letter rewritten for the role—I’m still stuck. Most of the time, I don’t even get a reply. When I do, it’s another polite rejection. It’s hard not to take it personally after putting in so much effort.


The truth is, upskilling in your late 30s or beyond isn’t the magic solution it’s made out to be, especially if you are a local. I’ve realised that age really does matter in the job market for s Singaporean, no matter what people say. Employers talk about valuing experience and lifelong learning, but when it comes down to it, they still prefer someone younger, someone who fits neatly into their expectations.


It’s not that I regret learning new things. I’m proud of what I’ve achieved, and I know I’m more capable now than I was before. But the reality is, all these new skills haven’t helped me break through the invisible wall that seems to go up once you hit a certain age. My years of experience in a different field are suddenly “irrelevant,” and my new certificates don’t seem to matter.


I’ve tried networking, reaching out to people, even offering to intern or volunteer just to get a foot in the door. Still, nothing changes. The advice always sounds so simple—“just keep trying, keep learning”—but it’s draining to keep putting yourself out there and getting nothing in return.


I’m not writing this to discourage anyone from learning. But I do think we need to be honest about how tough it is for mid-career Singaporeans in Singapore. Upskilling is important, but it’s not a guaranteed ticket to a new job or a fresh start, especially when employers aren’t willing to take a chance on someone older.


If you’re going through the same thing, I just want you to know you’re not alone. I’m frustrated, tired, and honestly, starting to lose hope. Maybe it’s time we have a real conversation about what mature workers actually need—not just more courses, but real opportunities.

Not true if u join security /phv/hawker industries....

 

[Hyruga]

Must start anew like fresh grad but as a older person

 

[Mr Totoro 38]

It is going to get worse in next 5 years. wana bet kkj, our population going to hit 6.66m by 2030 ? another 600K mouths coming to crowd every space we have.

pap will act blur and tell you 65% wanted this. pap is "making best effort" to slow down population growth....but 6.66m is bare minimum needed to keep sinkapore prospering.... no need chatgpt to make this PR speech..

prosperous FOR WHO? sinkies never ask.

i reckon would be more than 6.66m....

anyway we will NEVER know the REAL figure...but of coz if u find it is almost impossible to squeeze into train or buses....
then that is the answer lor

 

[socratesg]

GE over liao. All these late 30s and unemployed shd go do self reflect if they voted for this sad state of affairs of them. If yes, then ownself dig ownself grave lor.

 

[SpicyBird]

I’m writing this because I need to be honest about something that’s been weighing on me for a while.


A few years ago, I bought into the dream that upskilling would change my life. I signed up for project management modules, took data analytics courses, and spent countless evenings and weekends learning new things. I genuinely believed that if I worked hard enough, if I kept improving myself, I’d eventually land a better job or maybe even start a new career.


But now, after sending out hundreds of job applications—each one painstakingly customised, every cover letter rewritten for the role—I’m still stuck. Most of the time, I don’t even get a reply. When I do, it’s another polite rejection. It’s hard not to take it personally after putting in so much effort.


The truth is, upskilling in your late 30s or beyond isn’t the magic solution it’s made out to be, especially if you are a local. I’ve realised that age really does matter in the job market for s Singaporean, no matter what people say. Employers talk about valuing experience and lifelong learning, but when it comes down to it, they still prefer someone younger, someone who fits neatly into their expectations.


It’s not that I regret learning new things. I’m proud of what I’ve achieved, and I know I’m more capable now than I was before. But the reality is, all these new skills haven’t helped me break through the invisible wall that seems to go up once you hit a certain age. My years of experience in a different field are suddenly “irrelevant,” and my new certificates don’t seem to matter.


I’ve tried networking, reaching out to people, even offering to intern or volunteer just to get a foot in the door. Still, nothing changes. The advice always sounds so simple—“just keep trying, keep learning”—but it’s draining to keep putting yourself out there and getting nothing in return.


I’m not writing this to discourage anyone from learning. But I do think we need to be honest about how tough it is for mid-career Singaporeans in Singapore. Upskilling is important, but it’s not a guaranteed ticket to a new job or a fresh start, especially when employers aren’t willing to take a chance on someone older.


If you’re going through the same thing, I just want you to know you’re not alone. I’m frustrated, tired, and honestly, starting to lose hope. Maybe it’s time we have a real conversation about what mature workers actually need—not just more courses, but real opportunities.

Seriously how u wanna complete with fresh grad or even foreigners with cheaper salary? Do you really believe in govt that upskilling will help? Singaporean only deserved to collect tray in hawkers and work until 68yo. This is what we voted for.

 

[sAVaGEmP5]

Ppl must be punished for not what the market wants in terms of demand n supply, but what they think they want and can get it risk free. Go ahead and do whatever u want lo. Backfire u must be able to take calculated risk.

 

[kimsix]

i reckon would be more than 6.66m....

anyway we will NEVER know the REAL figure...but of coz if u find it is almost impossible to squeeze into train or buses....
then that is the answer lor

you are right, those tourists, st visa, students, sinkapore is too crowded, too competitive for COL.

65% have been boiled. Today is the floor now, the minimum worst to live with..

 

[Mr Totoro 38]

you are right, those tourists, st visa, students, sinkapore is too crowded, too competitive for COL.

65% have been boiled. Today is the floor now, the minimum worst to live with..

ponzi white paper was started in 2011 after pinky lost Aljunied.

Is not a yesterday problem. Still now 60% over still love it.

So...well...enjoy the overcrowding madness la. Those frogs deserved to be boiled....

 

[jimmy]

You picked data analytics - the one of the hottest and most competitive industries, what did you expect?

You know your competition? Straight As local grads, some with masters and PHDs. What's more, are you aware of the recent hiring freeze for CS grads due to over-hiring during covid, bad economic forecasts, and AI advancing enough to replace many junior devs?

In my company, a MNC, the entire ASIA analytics team got laid off. Officially, we are supposed to rely on the GLOBAL analytics team but the backlog is -forever-. So the local business teams saved one or two guys by pulling them in to do analytics/ops.

Unfortunately, I have no solution for you. Maybe try another industry. If this is meant to be a political thread, voting opposition isn't going to get you anywhere. Neither they nor PAP nor any other party have any solution.

Graduates embark on a 3 year course to complete their data analytics course and ask for a fresh grad pay of $5k.

If you take Skill Upgrading for 3 months, don’t expect to be on par with them and ask even the same $5k pay.

Instead, see if you manage to squeeze into internship. Company do hire if you show potential. But your pathway is always half way, don’t expect to be hired in the same tier as graduate.

You only graduate once. The rest is up to you.

 

[eternalxiii]

Graduates embark on a 3 year course to complete their data analytics course and ask for a fresh grad pay of $5k.

If you take Skill Upgrading for 3 months, don’t expect to be on par with them and ask even the same $5k pay.

Instead, see if you manage to squeeze into internship. Company do hire if you show potential. But your pathway is always half way, don’t expect to be hired in the same tier as graduate.

You only graduate once. The rest is up to you.

That was my point? TS said he went for upskilling (probably the 3 month course) and yet could not be hired. How can he go for 3 year course in his mid or late 30s to do career switch?

 

[jimmy]

That was my point? TS said he went for upskilling (probably the 3 month course) and yet could not be hired. How can he go for 3 year course in his mid or late 30s to do career switch?

Because the government just want to show there was some effort done. But if they don’t ring-fence, which they say will affect SG competitiveness, these skill upgrading is useless.

Somebody shown an advertisement for Skill Upgrading and it is often senior management enjoy the perks of these skill upgrading.

Don’t kid ourselves that a chemistry trained graduate can suddenly cross over to computer engineering and ace himself to be worthy of hiring. Only sales and marketing jobs are applicable.

 

[Travis_Touchdown]

neber listen to huatz the gahmen push for... they dunch even hab private sector experience... upskill huatz shiatz?? @fatscaryuncle

the only way chiu ish can upskill to change career ish become security guards... cleaners... dishwashers this kind...

 

[marksnow44]

In before;
Vote Wisely.

But But too late, you all just give that Tan sei Long mandate to bring in more FTrashes.