Why Older Workers Must Keep Investing in Themselves To Remain Employable

For boomers in today’s job market, seniority alone won’t cut it anymore. Nearly half of today’s workers plan to work past 65 or never retire, which means staying employed requires constant skill upgrades — not just hoping your experience carries you forward.

The Harsh Reality: Skills Depreciate Faster Than Ever

Here’s what many boomers don’t realize: job skills now lose value three times faster than they used to. For technology-related abilities? The decline is even steeper. Workers over 50 should expect to need upskilling between four and eight times over the next two decades of their career. That’s not a one-time investment; that’s ongoing commitment.

Nearly 60% of older workers admit keeping up with new technology is genuinely challenging. But sitting still means getting replaced. Boomers who want to stay competitive need to spend money on cloud-based computing skills, AI tools relevant to their roles, and other emerging tech capabilities. This isn’t optional — it’s survival.

Training: The Overlooked Career Insurance

Over 90% of workers aged 50+ have done job training in the past two years, but here’s the kicker: more than half paid for it themselves. Your employer might offer training stipends, but if they don’t, boomers who want job security shouldn’t hesitate to fund their own education.

The key is being strategic. Focus on training in skills that show up repeatedly in job listings within your field. Generic certifications won’t protect you; targeted, in-demand skills will. This is career insurance you’re purchasing with your own money.

The Physical Side: Investing in Your Body To Work Longer

About 30% of older workers would prefer less physically demanding roles to extend their working years. Repetitive motions, long hours standing or walking, and heavy lifting take their toll.

Smart boomers are investing in supportive footwear, ergonomic equipment, physical therapy, and strength training programs. These expenses directly impact how long you can remain productive at work. Think of it as maintaining equipment — because in this case, the equipment is you.

The Bottom Line

Boomers can’t rely on employers to fund their continuous development. The workers staying employed past 65 are the ones willing to invest in training, tech skills, and physical wellness themselves. It costs money upfront, but it costs far more to become unemployable.