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

[Kok leong]

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.

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