How do I know when I’m supposed to retire? | General financial discussion | Discussion forum

A First Person story from the Globe and Mail - 5 August 2018

How do I know when I’m supposed to retire?

By David Sheffield

“So, will you be the next one?” My much younger colleague is standing by my desk with a big smile. I pretend to not understand, but I know what she’s asking.

Canadian workplaces have been hit with a wave of retirements so massive that some have tagged it the grey tsunami. The term sounds ominous, conjuring up legions of aging people, such as myself, about to crash on the shore of an unsuspecting society – and in our drawback, drain the treasury and suck away the wealth of subsequent generations.

The demographics of this aging population are well known. In 1945, the end of the Second World War was celebrated with a prolonged bout of procreation that lasted for 20 years. The baby boomers – some 8.2 million in Canada alone – have fought a determined battle, but time is winning.

As a typical boomer, I have worked for more than half my life, my labour consuming perhaps the best years. Whether we like it or not, what we do goes a long way to define and, if we are lucky, enrich us. So how do we know when to stop? How will I know when to stop? Milk has a best-before date, tires have tread-wear indicators, but what about boomers? We admire and miss those who go out at the top of their game, beckoned by a bucket list brimming with challenges and possibilities. Then there are those who soldier on long after their campaign has ended.

I always knew that I did not want to be the old man in the corner. In my first office job, there was an eastern European fellow who reacted to almost everything with an incredulous guffaw and a dismissive hand motion. Nothing could, would or should change and we were crazy to think otherwise. We viewed him as a curiosity, an artifact, a communal granddad and an object of pity. His last major pronouncement in 1989, just before he retired, was that the Berlin Wall would never come down.

At the downtown station where I board the train for my morning commute, there is a poster ad for a personal-injury lawyer. Weathered but handsome in his white hair, sharp blue suit and power tie, he exudes confidence and wisdom and you just know he commands respect. No old guy in the corner, this man is in the corner office. He is the senior employee who we would like to be. Yet, for many, the final years are the worst of their career, feeling that their experience and expertise are utterly wasted. On a good day in the office, when I’m filled with accomplishment and stimulating engagement with colleagues, there is nowhere else I’d rather be. But on a bad day, I feel like a ghosted icon on my computer screen – there but not there, slowly sliding into irrelevance.

My company recently moved into a bright new office building: open plan, cubicles, all clean lines and glass. Goodbye spacious private office. We are like eggs in a crate now and I am in a corner. We have stand-up desks that rise with the push of a button and most of my colleagues now work standing, with headphones and music to quell the noise. This environmentally certified building recycles rainwater for use in the washrooms. A sign advises us not to drink out of the toilet or urinals. I feel as if I’ve landed in a new world and do not quite know what to make of it.

Some feel that to retire is to die. With the end of compulsory retirement in Canada, the decision went from a fixed date to a major life choice. Turning to the wise oracle of our time, Google, I search: When do you know that it is time to retire? Most answers are financially focused: “When you have saved 25 times your anticipated annual expenditures.” One site tackles how to be emotionally ready to quit work: “The ideal time to retire is when the unfinished business in your life begins to feel more important than the work you are doing.”

Sometimes I look for a sign, thinking I might pull the plug when someone stands up to offer me a seat on the daily commute. I ward this off daily by regularly offering my seat to others and, when standing, try to look relatively stable and comfortable even as my aching back screams for a seat.

At our office, the retirements go pretty much to script. Cake is served, a slideshow plays, eliciting remarks on how young everyone once was; speeches recount some career milestones – perhaps contributing to a new accounting system, being an enthusiastic member of the softball team, or maybe just having just been there a long time. The retiree, often with obvious discomfort at being in the spotlight, acknowledges the accolades, saying they will miss the people but not the work. And then they are gone. When my time comes, will I genuinely feel no regrets or just wish I could start over?

I stay in touch with recently retired colleagues and friends and, of course, the first question I ask is, “How is retired life?” The standard reply: “How did I ever find the time to go to work every day?” Like recent converts to a new religion, they speak of having the luxury of time, being able to savour the morning paper, travel at will and take up pickle ball. Pickle ball, promoted as: “the serious sport with the funny name that keeps you fit, socially engaged, and alert.” Will pickle ball be my retirement salvation?

Is time off more precious when it is scarce — an afternoon, a weekend, a three-week vacation? My father used to lament that he could never get everything done that he wanted to, “even in a month of Sundays.” Do I want a month of Sundays or years of Sundays? Would too much time go from being a blessing to a curse? Will I end up “just sitting at home growing tenser with the times,” to borrow a line from Bruce Cockburn? Yes, I could see that as a default option. It frightens me.

My still-smiling young colleague jolts me out of my thoughts. “So, will you be the next one?” I can tell that she, 20 years from now, will quickly answer, “You bet, I’m out of here asap!” Instead, I reply, “I’ll let you know. Just working through a few details.”