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

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, as well as 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 embark on a new career.

But now, after sending out hundreds of job applications — each one painstakingly customized, every cover letter rewritten for the role — I’m still stuck. Most of the time, I don’t even receive 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 realized that age really does matter in the job market for Singaporeans, no matter what people say. Employers talk about valuing experience and lifelong learning, but when it comes down to the crunch, 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 suddenly become "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 bettering himself/herself through constant 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.

#frustrated #rejection #losinghope #matureworkers #lifelonglearning