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WE ALL HATE LOSING—and life, alas, is full of it.
I’m not just talking about investment losses. There are the career successes we never had, the relationships that didn’t pan out and the purchases that fell short of our expectations. Almost all of us, I suspect, can recall countless situations that turned out less gloriously than we’d initially hoped.
Yet, even though my failures pain me, they don’t stop me from getting up each day and trying again. It strikes me that I’m the victim of some devious self-deception—and perhaps you are, too. That deception has three notable aspects.
1. Slights and failures are easily recalled, while praise and successes are quickly forgotten.
When I left The Wall Street Journal in April 2008, thousands of overly kind messages filled my email inbox. But guess what I remember? There was a lone email from a Journal reader who declared that he was glad to see me go. It’s almost as if my brain was telling me, “You did okay, but you could have done better, so don’t rest on your laurels.”
There’s a parallel with investing’s emotional rollercoaster. We build well-diversified portfolios, with an eye to reducing risk and capturing market returns wherever they’re happening, and yet we can’t help but be bothered by our investments that are lagging behind. This, of course, is classic loss aversion: We get more pain from losses than pleasure from gains.
2. Life makes sense in retrospect.
Hard work may set us up for career success. But whether we actually succeed often depends on luck—an element of randomness that doesn’t sit well with us humans, who desperately want to control our life’s destiny.
To be sure, we could always cite bad luck as the reason for our failures. But when it comes to life’s more significant events, bad luck isn’t a satisfying explanation. We want our life to make sense and, on that score, ascribing too much to luck doesn’t help. What to do? Enter the narratives we tell ourselves. One narrative I’m fond of: My failures laid the ground work for future successes.
In the middle of the night, I found myself considering my life’s achievements. These include getting into Cambridge, my long stint as a Wall Street Journal columnist, my two kids, the half-marathons I ran, my 2016 book How to Think About Money and this website. But here’s what’s striking about those successes: They were preceded by so many failures—or, if not failures, undistinguished results over many years.
But when I look back on those failures, I see a silver lining—that they somehow helped me get to where I am today by, say, knocking the rough edges off my character or by teaching me important lessons about both the world and myself. At the time, my life’s story might not have felt like it had any cohesion. But with the benefit of hindsight, I’ve managed to cook up a narrative where things make sense.
This narrative is especially clear when I think about my career. For instance, in many ways, my six years at Citi was a bust. I arrived to help launch a new online advisory service, but that venture was pretty much dead 15 months later. I then spent my remaining time at Citi as part of the U.S. wealth management business, doing daily battle with the lawyers and compliance officers who reviewed the stuff I wrote and the speeches I planned to give.
Still, in addition to some fat paychecks, I got a lot out of my time at Citi. I saw a bloated, politicized bureaucracy up close—and it made me realize how ineffective large organizations are. I learned how not to build a website. I got an inside look at how a brokerage firm works. I was compelled to write about every financial topic conceivable, including subjects like insurance and estate planning that hadn’t previously been my strength. And I was giving as many as 30 speeches a year, so I learned how to become a better public speaker. There was a huge silver lining—or that’s what I tell myself now, so the six years don’t seem like wasted time.
I imagine many folks have a similar narrative about their investment career. Early on, we often make all kinds of mistakes. But fingers crossed, we learn from those errors and eventually become more prudent investors. The early missteps were costly, but they came with a silver lining.
3. It always feels like there’s more to be done.
I first met Vanguard Group founder Jack Bogle in 1987, and last spoke to him a few months before his 2019 death. He was an astonishing man, relentlessly striving to leave his mark on the world—a drive that was still there right up until the end.
I’m not sure many folks could match Jack’s fire, but I think most of us have a little of that drive within us. In retirement, we might not be aiming for that next promotion or pay raise. But we’re still looking for a sense of accomplishment, whether it’s visiting all 50 states, losing weight, seeing our portfolio’s value hit some milestone, building something with our hands or putting together a great family reunion.
Indeed, this urge still afflicts me, even as I grapple with my dire medical diagnosis. I want to see HumbleDollar continue to thrive. There’s a slew of articles I still want to write. There’s a bathroom remodeling that Elaine and I are undertaking. I’d like to bring even more order to my financial affairs and get rid of even more stuff from the basement.
This striving is truly never ending. Like everybody else, I’m running on the hedonic treadmill, figuring happiness is just one accomplishment away, only to discover I never quite reach the finish line. Will I ever be content to rest on my laurels? I think not—because of the way we humans are wired: Relaxing may occasionally feel good, but it doesn’t feel nearly as good as achieving. Maybe that’s foolish. But it’s how our brains work.
Jonathan Clements is the founder and editor of HumbleDollar. Follow him on X @ClementsMoney and on Facebook, and check out his earlier articles.
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Jonathan – your column reminded me why it’s important to recognize all those who perform outstanding work, even those in the least glamorous roles. Just yesterday I introduced myself to the neighborhood landscaper who makes sure all my neighbors lawns are perfectly cut each week. Handing him a cold coke and telling him what a great job he does keeping our neighborhood looking top shelf caught him by surprise, but I know he appreciated the compliment. We had a saying in my business – “one awsh*t will ruin 10 attaboys.”
I can particularly relate to your second point, Jonathan – and even worked at the same financial institution to which you refer, only nearly three times longer, which was quite long enough, thank you. Dysfunctionality and bureaucracy, a perennial hallmark, mushroomed exponentially after the mega-merger of the commercial and investment bank, and posed a constant challenge. Still, that nexus allowed me to set foot in both worlds, with double the possibility for personal growth.
But ALL of that pales to having been posted, very early on in my career, for just a couple of years, to its Brazil operations. I fell in love with the country’s culture, and its people, and vowed to eventually return. When a bit later, that corporate relocation was not going to happen, I found the perfect excuse to make a clean exit and realize that objective on my own terms, where I remain today. And that is what made, not only that particular career choice, but my life in general, make sense.