Best Expenditures Boomers Should Invest in if They Want To Keep Their Jobs

Nearly half of workers say they plan to work past 65 or never retire, and boomers (age 61–79) are increasingly staying employed — but maintaining employability now requires active investment in skills and health rather than relying on seniority. Reports show over 90% of workers over 50 undertook job training in the last two years and more than half paid out of pocket; almost 60% find keeping up with new technology challenging, while the AARP Foundation warns job skills are losing value about three times faster than before and will require four to eight rounds of upskilling over the next two decades. The article advises older workers to prioritize market-relevant tech skills (cloud computing, job-related AI tools), and to spend on ergonomic aids, supportive footwear, therapy or strength training to remain competitive — ideally via employer stipends but often at personal cost — a trend that has implications for labor supply, retention, and demand for training and health-related services.

Analysis

The AARP Foundation reports nearly half of today’s workers plan to work past 65 or never retire and identifies boomers (age 61–79) as increasingly remaining in the labor force; Resume Now finds over 90% of workers over 50 undertook job training in the past two years and more than half paid those costs out of pocket. Almost 60% of older workers say keeping up with new technology is challenging, while the AARP warns job skills are losing value nearly three times faster than before and technology skills decline even faster, implying 4–8 rounds of upskilling will be required over the next two decades. The article recommends targeted investments in cloud-based and job-related AI skills and in physical aids such as ergonomic tools, supportive footwear and physical therapy; ideally employers would fund stipends but many workers self-fund these expenses. Market signals classify the theme as Technology/AI and Healthcare with a mildly negative sentiment and a modest positive market-impact score (0.12), indicating a secular demand shift for training, education technology, occupational health and ergonomic products rather than an acute market shock; risks include uneven access to upskilling and reduced discretionary spending among older workers.

Key Decisions for Investors

• Consider increasing exposure to corporate training and edtech platforms focused on cloud and AI upskilling as secular demand drivers, evaluate growth and contract metrics before committing
• Add selective exposure to healthcare and occupational-health service providers and suppliers of ergonomic equipment and physical-therapy services expected to benefit from older-worker expenditures
• Underweight or avoid pure-play operators in physically intensive, low-margin sectors that lack automation or explicit retention/upskilling programs, as they face higher turnover risk
• Monitor corporate disclosures for new stipend/benefit programs and L&D spend as near-term catalysts and use those announcements to time entries, and
• Watch consumer discretionary trends for signs that out-of-pocket training and health spending are crowding out other consumption and consider hedging broader consumer exposure if signs of strain emerge