3 Reasons A Baby Boomer Retiree Has To 'Un-Retire'

Many people look forward to the day when they no longer have to work, instead enjoying a satisfying and happy retirement. In fact, according to a 2024 MassMutual Retirement Study, 67% of retirees described themselves as happier, and 82% said they felt more relaxed, than when they were working. Meanwhile, less than 10% of retirees described themselves as feeling less happy or more stressed after they stopped working. However, retirement isn't always permanent. 

In 1994, per the U.S. Census Bureau, workers aged 55 and older made up only 10% of the workforce, whereas almost three decades later that group is now 24% of the workforce. Even worse, LinkedIn News reported that more than 13% of baby boomers "un-retired" in 2023, representing a five-year high.

There isn't a singular reason for baby boomers to un-retire. While many might be concerned with feeling bored or needing a purpose, other might simply want the opportunity to do something they never had the financial stability or time to do previously — such as starting their own businesses. However, some might simply hit a financial roadblock that forces them to return to work whether they want to or not.

Some baby boomers believe they're ready to retire — and look forward to having time to themselves to pursue their favorite hobbies – only to quickly realize they don't find their hobbies as interesting as they hoped. Others are simply left with too much time to fill during the day, and the reality that things like traveling, reading books, or playing golf aren't as fulfilling as they had expected. This can unfortunately lead to major retirement regrets.

Similarly, many baby boomers who retire find themselves feeling lonely. They might miss their daily interactions with coworkers or customers. Being disconnected from a daily routine can be unsettling and affect the mental health of retirees. Some people even experience physical health problems, meaning that a return to work can actually be necessary in order to remain physically healthy.

Kevin O'Leary, of "Shark Tank" fame, has even discussed his own challenges with retirement. Specifically, O'Leary issued a warning about early retirement – describing being unfulfilled and ultimately going back to the workforce. "I was bored out of my mind," he told CNBC Make It (via YouTube). For those who don't necessarily need the money, choosing to return to the workforce at least part-time after retiring can allow you to choose a job you find fulfilling, rather than focusing on the paycheck.

After working for many years and retiring, some baby boomers may have set aside money to leave to heirs. However, not all retirees will feel like money alone creates the kind of legacy they want to leave behind. Instead, they may feel a yearning to start a business that can provide a different kind of legacy. Plus, by starting a business after retiring, retirees can potentially spend more time with family by employing family members to help them find success. This could also serve as double duty to ensure family members are invested in the business — meaning they'll be ready to take over someday.

Beyond family and legacy, many baby boomers might simply feel the need to start a business as part of a lifelong dream to work for themselves and create something of their own. In retirement, they likely finally have the time and energy to give to a business. Similarly, many baby boomers will likely have access to seed money through retirement accounts that likely weren't available when they were still working. Or, they might even consider taking out a loan against a 401(k) account balance after retiring that they didn't feel comfortable doing beforehand.

Although you might look forward to retirement, if you don't pay attention to the warning signs that you're not financially ready to retire, you might run out of money too quickly. It's also possible that your retirement funds faced risky exposure to market fluctuations or even a sudden drop in your account balances. If so, you might need to go back to work to offset unexpected expenses. Some particularly common expenses include higher living costs and increased medical debt. As people age, their healthcare costs, in particular, typically increase — which can quickly eat away at savings and causing increased financial pressure.

For baby boomers living on a fixed income, sudden increases in property taxes can also be devastating — and they might even have to go back to work to keep their homes. Similarly, baby boomers relying on pension payments could find themselves out in the cold if their former employer suffers financial hardship — causing pension payments to disappear and leaving them without enough money to stay in retirement.