The What-ifs of Retirement
Retirement is a bittersweet journey.
It’s beautiful to arrive at a place in your life where you can be yourself, or at least more yourself than you were while working a corporate job, as many of us did for too many years. It’s painful, too, because you realize you have had to come close to the end of your days to be able to live on your own terms.
Disclaimer: I write this piece as a single white male without dependents. My perspective may vary from those with kids, grandkids, extended family, and so forth.
Retirement is a last hurrah, a final chance to do what you’ve always wanted to do, to be who you’ve always wanted to be, in a free and unfettered way. Everything from here on out is your choice, your prerogative, and no one can say otherwise. Dress the way you want to, go where you want to, listen to what you want to, indulge your hobbies, travel, start an encore career. There are endless possibilities. But there’s a catch. You’re facing your imminent decline and demise, and that casts a negative light on everything you do. Ah, to be young again!
Contemplating one’s demise makes retirement a bittersweet journey. You have to reckon with what might have been but wasn’t and never will be, and that reckoning results in endless what-ifs.
When I was fifteen or so, I made a vow to myself to live a different kind of life, a vow that I didn’t live up to. It was too hard, there was too little support, I didn’t have the clarity of vision or the right level of ambition… The truth: I didn’t have the guts to go against societal expectations, with the exception of a few years as a San Francisco punk rocker in the seventies. I let myself down, and now I stare back at a lifetime of what-ifs.
What if I had taken up the drums at nineteen and joined a punk rock band? What if I had traveled the world when I was in my twenties and early thirties? What if I had procured an Italian citizenship thirty years ago instead of in my mid-sixties? What if I had moved to San Francisco right out of college instead of waiting another two years? What if I had been a more mature and self-confident person in my twenties? What if I had dumped my crazy first girlfriend within a couple of months instead after a year and a half? What if I didn’t let people stifle my non-conforming spirit?
The biggest what-if for me is simply: What-if I had been able to be true to myself throughout my life rather than make the compromises I chose to make to earn a living, own a house, put money into a 401k, and basically sell out to corporate life? As a maladapted punk rocker in my twenties, I wanted nothing to do with straight corporate life. I wanted to avoid normal people like an Ebola infection. Yet what did I do? When my punk rock daze were through, I joined the ranks of the cubicle slaves working in technology, even earning a Masters Degree in English to advance my career. I lost sight of the dream I had had as a fifteen year-old.
What if I had not done that, but had done something else, something courageous, creative, adventurous?
Contemplating one’s demise makes retirement a bittersweet journey. You have to reckon with what might have been but wasn’t and never will be…
I realize now that the odds were stacked against me, as they are against all of us. Our culture seduces us with an easy path, a path of mediocrity and conformity. It makes forging our own unique path hard, risky, and challenging. Want to be an accountant, an engineer, a doctor, a plumber, a mechanic? The path is laid out for you. It might take some hard work and dedication, some long-term planning, but there it is, like a yellow brick road leading straight into the future.
But no one will ever suggest you travel the world on a catamaran, live among the lions in an African wildlife preserve, become a wandering mendicant, or create guerilla art on the sides of public buildings. They’ll gladly cheer you on for a life of bourgeois normality, one that fits into the overall scheme of things, but that will leave you dead and dispirited after each and every workday, aching for the relief of a two-day hiatus.
I can easily skate into the future without doing much of anything, living the usual retirement dream of low effort and few responsibilities. But that is not my plan.
Rather than drown myself in a sea of regrets, I am choosing to inform what remains of my time on this earth with the lessons learned from my past experiences. I realize that, like many people, I have a natural tendency to take the easy way out, to take the least risky route, to do the most obvious thing. This tendency, if allowed free reign, will sabotage my remaining years and make my life much smaller. If I want to, I can easily skate into the future without doing much of anything, living the usual retirement dream of low effort and few responsibilities. But that is not my plan.
So, no more regrets! It’s time to move forward, with or without fear. As the late Steve Jobs famously said:
The most important thing I’ve ever encountered to help me make the big choices is to remember that I’ll be dead soon…And when I remember this, I realize that all of the expectations and standards and restrictions of others and society mean nothing in the end.
I wish Steve had told me that a half a century ago, but that would be just another what-if…
