I Can’t Drive 65

The story goes, Sammy Hagar wrote the song “I Can’t Drive 55” after being pulled over for going 62 in a 55 mph zone in Lake Placid, New York (1). With “55” ten years in my rearview mirror, I have slowed down a little.

Last week I celebrated my birthday. One woman said, “Happy Medicare Birthday!” I didn’t know whether to feel happy or old. She insisted it was like turning 16 (you could drive), or 18 (you could vote), or 21.

I don’t know about that.

She tried another tack. “You get free stuff with Medicare!”

We all know nothing is free.

An acquaintance at my triweekly pool aerobics class, overhearing this banter, asked, “Are you retiring?” And the follow-up: “What are you going to do with all your free time?”

It is these questions that have been rattling around in my head.

Its meaning has evolved since the 1950s-1960s, when life expectancy was shorter and full Social Security benefits started at 65. The rise of employer pensions made the idea of retirement financially possible for the first time for many. Retirees were expected to slow down and enjoy leisure activities-like golf and fishing-they had deferred because they were working. Moving to Florida was looked upon as a sign that you had “made it.” Retirement was a reward for hard work and a well-earned rest.

A societal shift in the 1970s-1980s meant retirees were no longer viewed as “old people” who needed to rest. They were now seen as seniors in their “golden years,” an aspirational life stage that was more than just the end of work life. Early retirement became fashionable as this sector became consumers of the “good life,” traveling more and demanding products, services, and communities for older adults.

Retirement as an opportunity for personal growth came along in the 1990s-2000s. Instead of resting, retirees reinvented themselves. They went back to school or volunteered. Some wrote books or painted. They started encore careers. A longer life expectancy and better general health meant you could work 20 years post-retirement. The concepts of “semi-retirement,” “purposeful retirement,” and part-time work became common as individuals kept their hand in their work, but grabbed more time for themselves. These are the Baby Boomers who are challenging the stereotypes of aging-volunteering, traveling, and building their lives around lifelong learning. Some into their nineties.

The 2010s-2020s saw retirement as a fluid, individualized process that looks different for each person. With technology allowing many to work remotely, project-based work could often be done at any age, increasing the flexibility around retirement. Greater weight was given to work identity and the feeling of purpose connected to the work. The sense of community and contribution also factored into whether and when to retire, as the focus shifted from earning to meaning.

Today, many reject the term “retirement” entirely. Terms like “unretirement” and “encore entrepreneurship” are entering the conversation with a focus on purpose, social connection, and well-being. There is an emerging idea that retirement is not an exit- it is a transition to autonomy. A leap to creativity. A way to leave an authentic legacy.

This brings me back to my story. Am I retiring?

I “retired” from a career in finance many years ago to raise our children. This under-explored idea-”retiring to raise children” reshapes what retirement and caregiving mean. Historically, the two were nearly opposites: retirement meant stepping away from responsibilities, while raising children meant assuming them. In the last few decades, the line has blurred in ways that reflect broader cultural, economic, and generational shifts.

I propose a somewhat parallel view of retirement as it fits in with raising children.

In the mid-20th century, retirement and child-rearing existed at the opposite ends of the life cycle. The “ideal retiree” in the 1950s-1970s was a grandfatherly figure on a pension. He was free from family obligations except for bouncing his grandkids on his knee (permit me the extreme stereotype here). People did not describe women who left the workforce to raise children as “retired.” The idea of someone “retiring” into caregiving would have sounded odd.

As early retirement options became available in the 1980s-1990s, some people (usually women) left careers to care for aging parents or grandchildren. Family caregiving replaced traditional work as a new, unpaid form of labor, although few people recognized it as a kind of “retirement.”

In the first two decades of the 21st century, the idea of retiring to raise children took on new forms. A growing number of older adults are raising their grandchildren, often because of parental illness, addiction, or economic strain. Some retirees, although they are not raising their grandchildren, provide primary childcare so their own adult children can work. Retirement becomes not an escape from duty, but a reinvestment in family continuity. This aligns with more current definitions of retirement centering on purpose and connection, blurring the line with caregiving.

When I retired from finance, I stopped working for pay so I could work for family and meaning. Like any transition, retirement is hard.

Economic uncertainty is only the first reason retirement feels scary. Even well-prepared retirees worry about outliving their savings, rising healthcare costs, and losing their independence. More basic than money is the loss of identity and purpose that hits. Spending years defining yourself as a “manager” or a “teacher” or “fill in the blank,” and then that ends feels like a loss of part of yourself. Questions arise like, “Who am I now?” and “What will I do all day?”

The predictability of work gives the day structure. Working towards deadlines. Appointments on calendars. Meeting with colleagues, in person, or increasingly on online platforms. It is tough to muster internal motivation when you are used to this type of external discipline. Retirement can bring on a sudden sense of drift with its endless free time.

Oddly disorienting.

Workplaces are built-in communities. Even the wallflower can feel a sense of belonging as the work provides a reason for conversation. A source of purpose. Retirement can bring social isolation, especially if friends are still working. For couples, the sudden change of both being home together all day disrupts established rhythms and roles.

The psychological shift from being “needed” to being “optional” can be painful. The feeling of being dismissed or irrelevant upon leaving the workforce can feel like disappearing, especially in a culture that prizes productivity and youth.

I can appreciate retirement as a time of transition. I can also appreciate it as a time of grief. Multiple losses of identity, role, community, routine, and purpose have to be processed before the gifts of retirement can shine through. Society does not always validate these mixed feelings. We are told to be happy about retiring. This can make the sadness feel isolating, or we feel ashamed about it.

I have come to terms with the fact that I served a purpose with the highest meaning by retiring to raise our daughters. Dollars can never measure the value of this work. At 65, I am fully invested in the idea that retirement can be our period of maximum creativity. A time to pursue dreams, connections, and build community. These are the decades to really look at the bucket list we made in our 40s and decide what we want to check off. This is our chance to become our best selves by looking everywhere for wisdom-to those older than we are, and to the younger generation coming up with new ways of thinking. I am a lifelong learner with no shortage of books I want to read, trips I want to take, and skills I want to learn.

I don’t have time to go back to traditional work.

And I can’t drive 55.

Love, Alice

(1) www.songfacts.com I Can’t Drive 55 by Sammy Hagar retrieved 11/6/25.