Should You Retire If You Can Afford To?

There’s money in the bank after working hard for decades. The kids, if there are any, have (finally!) left home, making you and your spouse, if there is one, the so-called empty nester. In this sanguine scenario, you can stop doing the 9-to-5 grind and kick back to do, well, whatever.

Considerable numbers of financially privileged baby boomers (and some Gen Xers and millennials who hit it big) are now in such a fortunate position. But many well-to-do boomers are not retiring, at least in the way that their Greatest Generation parents did. Moving to a condo in a warm and sunny place (think Del Boca Vista in the memorable Seinfeld episode) to play golf every day and eat dinner at 5:00 pm just doesn’t have the same appeal for a generation known for an ethos of achievement and for rocking the boat. Instead, most boomers continue to work (assuming they have not been dismissed from Corporate America because of their age), padding their estates that will be left to children and grandchildren.

Is this a good thing? Maybe or maybe not, depending of course on the individual. I’m finding that those who are extending their second act into their 60s and 70s simply don’t know what else to do in their third act, as that is something not taught at Harvard Business School or anywhere else. We are well trained to get and keep jobs but little if any attention is paid to what to do after our careers run their course and to the range of emotions that are attached to retirement. So we keep doing what we know how to do, even if we may feel this is probably not the best use of our limited time and energy.

The most contented boomers I know are those who were effectively pushed into their third act by an outside force, meaning it was not really their choice to take a different course. These folks realized they had to reinvent themselves in some way, if only because they needed a reason to get out of bed in the morning. For Americans, at least, work comprises a huge component of our personal identity, and the end of a long and successful career often brings a sense of loss and uncertainty of our place in society. It is thus no wonder that many are reluctant to retire even if they feel that doing something else may offer more meaning and purpose in their lives and in the lives of others.

I understand that it takes a considerable amount of courage to give up whatever it is that one has done well for decades, especially given the degree to which work defines us as individuals. Americans are worker bees, and the prospect of having little or nothing to accomplish is a scary and unsettling one. How will I fill my days? one might ask oneself, with the loss of the social network that often comes with a job another major and legitimate concern.

The false but deeply rooted belief that one has no value or worth in society without a paid occupation of some kind compounds the dilemma of whether or not to retire. External pressure reinforces the natural urge to stay at one’s job, particularly that from financial experts who continually and sensibly remind us of how much money is needed to retire due to greater longevity and escalating healthcare costs. (Some advisors of the smaller “die broke” school of thought tell their wealthier clients to go enjoy life while they still can.)

I’ve found that those who’ve opted to pursue an alternative endeavor or had one thrust upon them are usually happy with the way things turned out. It’s a big world out there, after all, and many of us live relatively narrow lives. Happily, learning does not recognize age, and there is an unlimited amount of knowledge to gain if one seeks a greater understanding of the universe or even a small part of it. Starting a business is a popular choice, as older adults appear to be naturally inclined towards entrepreneurialism. (The numbers back that up; more than 25 percent of new entrepreneurs were between age 55 and 64 in 2019, according to the Kauffman Foundation.) Giving back in some way or helping others are prime ways to spend one’s third act, as research shows that older brains are hard-wired for altruism and to serve as voices of reason and wisdom.

Baby boomers wondering if they should stay the course for as long as possible or instead choose a different path might ask themselves a few questions. Am I making the best use of the unique set of skills and resources that I have developed over the years? Am I still intellectually challenged, and do I wake up excited about the day’s possibilities? Can I leverage my experience in a more productive and rewarding way? Will I later regret not exploring doing something I always dreamed about, say traveling the world, learning a new language, embracing a form of spirituality, or perhaps finishing that novel that has been stuck in my drawer since the Reagan administration?

I believe the ultimate questions to ask oneself at this stage in life are: “Have I fulfilled my potential as a human being?” and “Have I somehow made the world a better place during my time on the planet?” The answers to those questions are likely to provide the best directions to reach one’s most gratifying destination.