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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.
A lot of people strive to leave their mark on the wider world in some way, but it is almost always inconsequential in the long run. Think about all of the former U.S. Presidents that you can’t even name.
Unfortunately, you may be in denial. I hope you can be satisfied with what you were given and what you have achieved.
Of course, you won’t print this comment because it interferes with your narrative. No matter, I only want the best for you.
“Never quite enough” is truly a double edge sword – for good, as it pushes us to strive for better, or for ill if it is used to wound, to hurt, to make us feel inadequate. I use it for my work, life or creation to keep improving my skill and not rest on my last laurel. I even want to be the best in my silly word game I play everyday.
I see that in you, Jonathan. We can’t help it as we are part of the forward looking, optimistic kind of people who want to be “better” at everything.
I would love to know what reason that lone reader gave for being glad you were leaving the Wall Street Journal.
Your Getting Going columns were the foundation of my investment knowledge. I can’t imagine why anyone would want to see those columns retired.
You continue to have my fullest admiration. I followed you for what I could get. Now I do so for all you give.
Jonathan:
We both have a stint with Citicorp in common, and like your experience, I brought them the knowledge, skill, and experience to launch a successful program. After 18 months, I knew they would never successfully implement it, and I took my credentials elsewhere. Also, like you, it was a learning experience, guiding me away from major bureaucratic organizations later in my career.
I also had to chuckle when I read about “that one negative email…”
In 2009, I entered my third career, as a college professor. I taught the things I had been doing for the past 38-40 years, and my students loved the fact that, unlike the majority of academics, I actually had “walked in their shoes,” having had “real jobs.”
College professors receive surveys from students whenever courses are completed. These surveys result in “rankings” and numerical scores related to “success.” Although in my 15 years at my institution, I was always ranked in the top 2% of professors, it always grated on me when I saw negative comments from students. Obviously, these surveys were anonymous, and I never knew exactly who made the occasional negative comment, but it took me a few semesters to realize that I should be focused on the 99% of my students who were thankful and appreciative of my efforts on their behalves, and not the 1% of malcontents, who found fault like there was a reward for doing so.
I retired this past January, and while I do miss being involved in the growth and success of the thousands of students I impacted over my three different careers, I am finding other ways to impact my world, and enjoying these new efforts as well.
One of my favorite quotes of all time…
“I am only one, but I am one; I cannot do everything, but I can do something. What I can do I ought to do, and what I ought to do, by God’s grace, I will do.” Edward Everett Hale
I always felt that way about my student evaluations. I could have 19 students and 18 thought I was great, and one was like “meh,” and I’d obsess about what I could have done to make that one person like me more. Human nature, sounds like.
I share many of these experiences. As a young doctor, I was convinced I could have a great career in academic medicine research and publishing. I took a job at a top flight medical school that required me to work at the VA hospital. Jonathan the VA makes Citi look like the most efficient organization in history.
To succeed in academics I had to not focus on patient care, which reinforced my understanding that what I really loved about medicine was taking care of patients, the more complicated the better. As the VA was impossible for efficient patient care, I knew I had to leave and eventually joined a private practice where I stayed 30 years, and loved every minute. I realized I had found my ideal job, and was very appreciated by my patients, many of who still keep in touch.
Excellent article, Jonathan. Thank you!
” Life makes sense in retrospect.” I feel blessed to able to look back over my life. Many of my classmates did not make it this far. What seemed like being in a giant pinball machine at the time can be viewed with the perspective that all that happened put me in position for the good things that happened. I’ve kind of forgotten the bad things. Or they don’t seem so bad now.
For many very capable people, there is always that little voice in the back of your mind telling you that you can do whatever it is better/that you should have done it better. It might be a touch of perfectionism, or perhaps OCD. For men especially, there is a strong ethic taught to most that they should be self sufficient and want to do things well. Some might call it pride. The stronger these feelings are, the more time we spend polishing that article, practicing that speech, etc, the more critical we are of how our work product turns out, or of how well we do at moving the organization we are part of towards it’s success.
The only antidote for this is to learn to be satisfied with what we have done. This can be hard to do. Fortunately, many have supporting family who have benefited from our hard work and let us know that they appreciate our efforts. And there can be other voices out there telling us that “we did well” if we just listen.
Another great article, Jonathon. Even the great Albert Einstein received much criticism, a high school teacher scolded him, ” you will never amount to anything, Einstein !”
Albert had a disdain for formal, structured education, feeling it inhibited innovation, etc. He also skipped many lectures at the Swiss university, where he received his doctorate, The Swiss Polytechnic Institute. He had his friend, Marcel Grossman, take notes for him.
His parents thought he might be mentally retarded , he didn’t speak with any regularity until age four. At that age, his father gave him a compass, and he inquired why the needle always pointed in the same direction.
Einstein taught himself Euclidean and plane geometry by age 10, and prior to age 15, had mastered both integral and differential calculus.
Einstein confessed he made several blunders during his life, the biggest one being his thoughts that the universe was static, not expanding.
Even on his deathbed, he continued to work, attempting to find a ” Unified Theory Of Everything,etc.” I feel if Einstein made mistakes and was criticized and so forth, clearly the rest of the world should not be overly concerned when we mess up!
I wish to add, Einstein was once asked if he kept a notebook with him so he could record his theories and the like, he replied, ” Oh no, it is so rare that I come up with an idea worth writing down.” I think its safe to say, when he did manage to have an idea, it turned out to be a pretty good one.
I live better than the royalty of a hundred years ago in many areas, including entertainment, medical care, etc. I’m grateful to wake up every morning as a free man in retirement with enough money to do darn near anything I want. I don’t even think about my failures as I won the big lottery by being born in modern America.
Your words about Jack Bogle’s drive and how “striving is never truly ending” stand out in this piece. Ask a runner about the race he’s just run and no matter how well he did he won’t care all that much about it. We see the same thing with boxers, who routinely use the first exuberant moments after a win to stand sweating in the ring and issue a loud challenge to their next opponent. The opponent vanquished is forgotten immediately and the focus moves to the next fight.
If we do it right, there always is a next fight, or at least something to be curious about, something to begin, even if we’re not certain we can finish it.
I totally agree Jonathan. As the central IT director, I could get 10 compliments from customers and one critical response. Guess which one I took home with me at the end of the day?
Our organization wrestled with the central IT or decentral IT question for years. It made for a toxic political environment. Sometimes a customer would send a harshly critical letter to senior management about me and my department. Even if the criticism was unfair or unfounded, I realized I could learn from it because people never criticize your strengths. It is always your weaknesses. I might defend myself or my department, but I used this as an opportunity to improve our weaknesses.
Yeah, you nailed my life with all 3 points. I can’t imagine being more happy with my life than I am now. Chris and I just celebrated 22 years together. Had I done anything different there’s no telling where I’d be today.
Amazing. That’s it.
Great article and perceptive insights, Jonathan. I had one notable, very public failure early in my career that paradoxically resulted in a significant positive impact on my career-or so I tell myself. Maybe I’ll write about that sometime. As to the summing up phase you find yourself in, there’s a verse in Ecclesiastes to the effect that “the end of a thing is better than its beginning.” When I was young, I had a lot of uncertainty and angst about how my life would unfold. It’s much better now to be able to look back and be grateful for the actual journey. Yet, I can’t say I believe my life has been simply a series of random events, although it may appear that way sometimes. Of course, your third point resonates strongly with me–I think you know me well enough by now to not be surprised by that.
Johnathan you are so right. Ten things could go well in a day and one could be a disappointment……we find the one disappointment clouds our mind.
Here’s a quote I try to live by.
“It is impossible to be grateful and unhappy at the same time.” Matthew Kelly
Simply said, another great article. I can relate to so many of your points. And having experienced the brief pleasures of success and the painful and often propelling periods of not meeting my own expectations or someone else’s. Life’s many lessons that carve us into who we are or will become. I think the victory is to have balanced the two or at least have a sense of perspective about the total picture of your life. Thanks Jonathan for helping to remind us all to look at the total picture of life.
Truer words have never been spoken. My failure at one thing motivated me to the next success until I needed to learn another lesson with another failure. Now I’m pretty happy because all I want to do is live my life, there are no mountains I want to climb. I’m happy to do my chores, listen to great music, read good books and chill. Thanks Jonathan!!
Much truth here. Regarding #2, I am so fascinated by the stories (narratives) we create to make sense of our lives. Thanks Jonathan.
I share Jonathan’s amnesia about past accomplishments, praise, and laurels. But, from an early age I have kept a file—first paper-based, later electronic—of good reviews, emailed compliments from colleagues and people I have served, etc. I did this explicitly so that in later life, when my memory would likely dim, I would not forget them, At times over the years I have visited my “Kudos” file when I needed a reminder!
Jonathan, thanks for a very thought provoking article. In retirement, I’ve had this nagging thought that I should still be contributing something to the world. It’s partially a feeling that I’ve been blessed with skills and experience that are valuable, and that it would be selfish not to use it in some way. I think that will stay with me throughout my (cognizant portion anyway) life. I also hope to keep learning as much as possible. Good luck with the bathroom Reno.
Rick, your contributions to AARP’s tax program is most notable. I learn a great deal from your articles about that work. How many people finished their return with you and went home feeling much better? I’ll bet more than you can count.