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

[TheITGuy]

Reskill into IT and you would likely find a job in IT

 

[matrixx]

Late 30s is not old. Also, what are the courses you took? If it's courses in demand like cissp or oscp, I'm quite sure it would be valued.

Correct. I've seen ppl in late 30s and early 40s easily transit into cybersecurity by taking these valued certs. And these certs are no joke. Takes a lot of grinding and effort.

TS didn't say what courses he took. I hope he didn't take those those courses offered by ntuc, udemy or in Tiktok lol. That will explain where these courses didn't help him.

 

[New_Account]

ts u really believe "upskill" can beat 3-4 year degree

 

[jeffrey745]

Correct. I've seen ppl in late 30s and early 40s easily transit into cybersecurity by taking these valued certs. And these certs are no joke. Takes a lot of grinding and effort.

TS didn't say what courses he took. I hope he didn't take those those courses offered by ntuc, udemy or in Tiktok lol. That will explain where these courses didn't help him.

Do u mind sharing wad certs they took? Blue or red team cyber?

Did they take OSCP or CCNA?

Like u mentioned, these certs are not easy, especially for beginners... So it really takes time and lots of effort...

 

[windwaver]

There was an election candidate that said upskill and reskill today

 

[sg-united]

@TS, are you currently employed? If no, was this the reason why you go for courses?

 

[Milodrink]

dunno why u all buy into the upskilling nonsense.

SME boss dont see all this.

Evil boss only want better cheaper faster


Just smart enough to slog, but dumb enough not to question anything.

 

[Milodrink]

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.

This true

 

[fly1111]

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.

Agree. Problem is the HR. The HR doesn’t know how to recruit the right people. So they will always go for the safest choice. U can upskill the whole nation. If the HR is stupid then nth much will change.

 

[haxyer]

4 years ago, I have done part time specialist diploma in a local poly which took about 1 year to complete and the class I was in, around half of them are foreigners sponsored by company or self sponsored. so not just locals are upskilling, foreigners are doing it too

in MNC that I worked in, self development can be viewed as yearly goals but in SME that I worked in, they don't really care about self learning and it runs the risk of being outdated especially working in tech. I think more can be done to this thinking

 

[firsttimebuyer]

Normally it is easier if you assume a new role and then up skill from there. But getting the role is another challenge.

thats the proble,. its a catch-22; people won't hire without relevant experience; but not able to get relevant experience unless get hired.

 

[firsttimebuyer]

What are you currently working as? If your job is too different and there's no way to apply the knowledge gained from the various courses to your current or future roles, all these upskilling is quite pointless.

Unfortunately, it's a fact that employers prefer hiring young freshies, not old freshies even when both are asking for the same pay

i took the time to think and I think i made too many wrong choice; currently backend admin plus quite a lot of PM work....

 

[firsttimebuyer]

Correct. I've seen ppl in late 30s and early 40s easily transit into cybersecurity by taking these valued certs. And these certs are no joke. Takes a lot of grinding and effort.

TS didn't say what courses he took. I hope he didn't take those those courses offered by ntuc, udemy or in Tiktok lol. That will explain where these courses didn't help him.

Looking back on hindsight, i took useless courses.

 

[FORSTA]

is like that one, better stick to one profession rather than trying to be a master of none

 

[sanukboy]

Correct. I've seen ppl in late 30s and early 40s easily transit into cybersecurity by taking these valued certs. And these certs are no joke. Takes a lot of grinding and effort.

TS didn't say what courses he took. I hope he didn't take those those courses offered by ntuc, udemy or in Tiktok lol. That will explain where these courses didn't help him.

Could be "Inter"?

 

[Brionic]

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.

this will continue to increase as more sinkiekias are replaced by foreigners

as mandated by the govt, sinkiekias have to serve these "PMET" as they bring value and jobs to us

 

[clearwhitesky]

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.

True, suggest mom to allow FT to drive grab and send food… so the all those so called mid career switcher can have more competition.

 

[Hyruga]

Be careful who you vote for. Vote wisely...5 years later

 

[kimsix]

this is 100% happening on the ground.

our income will flatten by 40, and still have higher risk of dropping down a few tiers

pap chasing never ending shrinkflation, importing more mouths and high networth people are killing locals.

but 65% still in lala land, happy to read only good stuff.

 

[mutare ad melius]

this is 100% happening on the ground.

our income will flatten by 40, and still have higher risk of dropping down a few tiers

pap chasing never ending shrinkflation, importing more mouths and high networth people are killing locals.

but 65% still in lala land, happy to read only good stuff.

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.