I SPENT NINE YEARS at English boarding schools. The food was beyond disgusting. The buildings were cold and drafty. I was constantly bullied. I would go as long as 14 weeks at a time without seeing my parents, who were based first in Bangladesh and then Washington, D.C.
But I also knew I was getting a good education, and I opted to stay when I had the chance to return home and go to the local U.S. high school. I had this notion—perhaps partly the result of my Catholic upbringing—that there would be a payoff for my suffering, that if I kept my head down and kept studying, I’d be rewarded. It was a strange act of delayed gratification for a teenager. But it worked out. I managed to gain admission to one of the world’s great universities, though it was a close call and, no, that isn’t false modesty.
After I left boarding school and before I went to Cambridge, I made a conscious decision to reinvent myself as someone more outgoing and confident. I wanted to leave behind the tearful, vulnerable kid I’d been, and I knew there’d be few students at Cambridge who knew my old self. That, too, worked out. I arrived at college determined to make my mark, and soon found myself editor of the student newspaper.
I think that adopted self-confidence, coupled with the mindset that if I sacrifice and suffer now, I’d be rewarded later, was the reason I had a successful career and became a reasonably good amateur runner. I think it’s also a key reason I’ve been a prodigious saver and that I’ve had success as an investor, tenaciously buying stocks when things look bleak.
That willingness to sacrifice for future benefit is still with me—but it’s an attitude I find harder to justify. After all, at age 60, if I sacrifice now, will I still be around to collect my reward? As my stepfather would joke toward the end of his life, “I don’t buy green bananas.”
This is obviously an issue for those—like me—who have led frugal lives and have thoughts of spending some of the money they’ve amassed. But it’s also a question for those—again like me—who continue to work hard in their 60s, imagining there will be some reward down the road.
To be sure, work itself can be rewarding. There can be great pleasure in striving for something we care passionately about. When we choose to retire, we’re declaring, “I’ve accumulated enough.” But we aren’t necessarily declaring, “I’ve done enough.”
Still, there’s a crucial difference between what we do during our career and what we do once we’re retired. During retirement, how we spend our days is largely our choice. We get to focus on activities we enjoy and find fulfilling. Typically, we’re living in the moment, rather than building toward some future success—a promotion, a pay raise, some goal that’s important to our employer.
Many folks are happy to get off the career treadmill. But for others, including me, calling it quits doesn’t come easily. We humans are inherently restless. We want more stuff, more money and, yes, another success. And when we get these things, we quickly grow dissatisfied and start hankering after something else. We never achieve that final, fully satisfying triumph that we crave.
This is something I think about way too much. For the past few years, I have—in my head—been negotiating the terms of my surrender to the joys of retirement. I’ve been trying to figure out when I can declare that I’ve had enough career accomplishments and I can shift into retirement mode, focusing less on some elusive future success, and more on enjoying the here and now.
As I’ve written before, I think it’s important to figure out ahead of time what success looks like, so we find it easier to declare victory. Four years ago, I decided that success for this website would be notching 500,000 pageviews in a month. HumbleDollar got there in February, with 510,000 pages viewed. To be sure, the site remains minuscule by internet standards. Still, I’m declaring victory.
Do I feel a sense of lasting triumph? No. But I suspect that this is as good as it’s going to get for HumbleDollar, so I’ve decided to tamp down my ambitions for the site and work a little less hard going forward. As you might have noticed, the site has been publishing somewhat fewer articles of late, often just one new piece each day. Fear not: I have no intention of shutting down HumbleDollar. I hope to keep the site going for many years. I’m not done doing—but I am done chasing success.