A popular theme for Substack writers is to tell cautionary tales about career burnout. It’s the younger writers on this topic who particularly resonate with me. People in their thirties or early forties who have most of their life experience ahead of them, yet are already wise enough to be asking some of the most challenging questions of themselves and of their readers:
How do I balance career and family?
How do I avoid burnout and take care of my health?
How do I keep invidious comparison and memetic desire in check?
What is true success?
What is enough?
I don’t recall asking myself these questions in my thirties, in my forties, or even in my early fifties. I can recall stress over these topics that affected my health during those years, but I kept that stress to myself until my wife intervened. I didn't write about my stress, and I didn’t have the benefit of reading about how others were confronting their stress.
Emma Gannon is one of the leading Substack writers on this theme, having suffered from her own traumatic burnout a few years ago when she was about thirty. She’s written a fluid, bestselling book about the topic called The Success Myth. 1
In her last chapter Emma offers a concise summary in the form of a triptych of precepts contrasting old success with new success.
“Success used to mean never-ending wealth. Success can now mean time wealth.
Success used to mean constant busyness. Success can now mean resting.
Success used to mean always striving. Success can now mean knowing what enough feels like.”
I’m 61 now, my kids are adults, and my formal finance career is done. So I’m at a different stage than these younger writers. I still ask the same questions, but with a different perspective and different definitions about the meaning of success and “enough.”
As to burnout, that’s one fear I’ve literally put to bed. Some in my family would say I’ve made “resting” an art form, meaning I always seem to be either “relaxing,” watching TV, or napping. Sometimes, I can “accomplish” all three intermittently at once. 2
So now for me it’s really the question of “enough” that I ponder. Materially I have more than enough and I know it.
But my questions about enough don’t stop. They become different.
I wonder about the impact I’ve had, my current relevance, and the narrowing opportunity set for future impact. The word “legacy” starts creeping into my mind. Confusingly so, for what does a legacy even mean?
And while I may no longer use balance sheets as a measure of comparison with others, I still compare myself using the far more elusive measures of impact and legacy. Sometimes the comparisons can be enlightening, sometimes they’re just as galling as any other invidious comparison/mimetic desire. 3
One of the founders of my firm, John Angelo, had a perspective on life that I find usefully challenging.
John had a “one of the boys” charm, with a full head of dark hair and an unlined face to match. Whether he was being critical or charming, he always had an air of confidence, just short of a swagger.
He made you want to be liked and approved by him.
John became an extraordinarily wealthy and successful man. He used to come into my office, however, and bemoan the existence of a few rival investment management firms that were bigger.
When I’d point out that he’d co-created a great firm, he’d shake his head and wave his hands to dismiss my attempts to soothe him. John always wanted more. “Enough” was for him a foreign concept.
I should mention that John was certainly not a classic workaholic. He had a talent for mixing leisure and family with business. He knew everyone, and when he was socializing he was deepening connections that were beneficial to the firm.
John once remarked that all the nerdy “A” students––I know he was thinking of me!––ended up working for all the sociable “C” students––definitely him.
I had no comeback to that. He was right. I was a better student and knew more than he did about most subjects. But I worked for him, and the better I did at work, the better he’d do as a founder of the firm. He’d always be richer than I’d be.
John was a lot older than I am now when he was still charging ahead to grow the firm. He succumbed to cancer in his mid-seventies, working almost to the very end.
I wonder, did John have the right idea? To live a life where he never questioned what success meant for him? Yes, he always wanted more, but it’s hard for me to credit that this desire caused him real pain or stress.
Maybe a “C” student like John, blessed with the ease that comes with a privileged background, immense charm and confidence, and force of personality, wouldn’t ask the challenging life questions that can lead to doubt and stress.
Someone looking at John and me from afar might think of us as more similar than different. Both privileged, both working in the finance industry at the same firm, both wealthy, albeit at different scales.
But because of the similarities, the differences become more instructive. I thought then, and still think, that my knowledge entitled me to encounter the world with a sharper, deeper, brighter lens than John’s. But that intellectual bent made me less likely to go all-in to my career, made me more of a questioner, more of a doubter, ultimately less sure of myself.
Over Thanksgiving, I watched the movie Oppenheimer, and it delivered an unexpected blow to my self-esteem. My intellectual lens into the world may have had an edge over John’s, but Oppenheimer’s lens was like that of a different, more highly developed species.
Oppenheimer was a polymathic genius––I’m taking the movie portrayal of him at face value. I remember watching the scene where he’s translating Sanskrit to his lover and thinking that I couldn't begin to fathom a mind that can learn languages by the dozen. I know only English.
Or the scenes where his conceptual breakthroughs in physics are represented by visions of stars, fire and flame. In retrospect, that may have been a movie director’s outlandish attempt to make thought come alive, but as I was watching the movie, I took it in as real.
As well, I compared myself to Oppenheimer’s impact on the Manhattan Project. He used his great intellect and energy to bend physics to his will and became the Project’s key scientific player, a king among princes, leaving an indelible impact on the most momentous of world events.
In contrast, I thought of the circumscribed ambit of what I could look forward to doing. That thought made me feel small and insignificant. Like Burr in Hamilton, I was far from any room where the consequential things were happening.
My envy of Oppenheimer, expressed as a feeling of inferior intellect and insufficient impact and purpose, faded once the movie ended. I realized just how ludicrous it was to compare myself with the scientist who had split the atom.
To adequately appreciate the absurdity of my comparison with scientific genius, you’d need to see me fumble with a pair of kitchen tongs or struggle to operate an electronic toaster-oven.
For the rest of the Thanksgiving weekend, I forgot about the movie. I was pleasantly distracted by family meetups, a decent Netflix binge, and Red Zone. 4
But while my transient envy of Oppenheimer had elements of absurdity, I couldn’t deny that I had felt it. My takeaway was that my sense of “enough” remained vulnerable to doubt.
Once again, from Emma Gannon’s precepts:
“Success can now mean knowing what enough feels like.”
Success is like a victory. But neither John Angelo nor Robert Oppenheimer declared victory. John because he always strived for more, Oppenheimer because his life after the use of the atom bomb was marked by profound doubts about the impact of what he’d done. Doubts that troubled his conscience and damaged for some time his reputation.
I don’t ever want to declare victory either. Because for me, it would be a Pyrrhic victory, a defeat disguised as a victory.
The phrase Pyrrhic victory comes from the Greek general Pyrrhus who Plutarch records as saying after a costly victory over the Romans in the battle of Asculum, "If we are victorious in one more battle with the Romans, we shall be utterly ruined.”
Victory for me over enough would mean victory in all aspects: not only material, but impact, and legacy. So then what would get me up in the morning?
Family and friends, sure.
But I need to feel productive, I need to feel that I’m helping people. That’s the impact I crave.
Question for the Comments:
How much free time would you want?
Office Space clip: The classic movie sendup of office life by Mike Judge, creator of Silicon Valley. We watched it last night and it held up wonderfully.
In addition to Emma, a few of the other younger writers that illuminate these questions for me with their personal essays include
andI will share a secret. Often when I’m “resting,” I’m actually reading Substack essays, commenting on them, and working on my own Substack posts.
I use the terms invidious comparison and mimetic desires as a pair as they’re both related to envy. Perhaps someone more knowledgable than I am can dissect the differences.
It’s come to my attention that some people are unfamiliar with Red Zone. So this is a Public Service Announcement. Red Zone is an enthralling, commercial free, all day Sunday live broadcast of the most consequential and exciting plays at any moment of every NFL game being played. For a football fan, it’s heaven.
Enough! Let yourself be. I'm 75, not wealthy in the usual terms yet the loves in my life make me rich beyond compare. That is enough. I see my children as parents, raising my grandchildren. Surely, that is enough even in terms of legacy. My granddaughter uses stories I've told to make the same points I do. That is enough. My daughter, when the question came up, offered me her kidney in a NY minute (the shortest measure of time known to man). That is enough. I could go on and on about my kids, grand and Kim, the love of my life, but that would be too much. I see a world full of conflict but I see the next generation's good hearts, making their communities a better place. I have a hobby that affords me all the creative opportunity I need only steps away. I have enough. From the little bit I gather about you, David, you have more than enough not taking your business success or financial wealth into account at all. So, I say to you, enough of the chase for enough. Perhaps you already have it and what you do going forward, your wonderful efforts to help others, can simply be more than enough and wouldn't that be good?
This is a timely piece for me. Having spent the last 24 years in military I will be retiring in about six months. My wife and I came to this decision because we were seeing diminishing returns on continued service. I have spent so much time deployed and missed out on so many family things that I began to count to opportunity cost. While I have been successful in my career and worked hard to climb the promotion ladder, the future of my career doesn't change much. If I continue serving then it means more deployments, more missed family opportunities, etc... The financial benefit of continued service does not compensate for the burnout I feel. I am in my mid-40s and I am asking myself where I can do the most good. Like everyone, I want to be financially secure but I think doing something with the second half of my life that pays off in contentment and happiness will be even more valuable than chasing promotions and paychecks.
My younger brother also retired from the Navy about a year ago. He asked many of the same questions you pose and that I am asking myself. He wanted to have an impact not just on his own family but for others in similar situations. I found it interesting that you discussed legacy because he created his own business call A Long Legacy. Obviously a play on our name but also relevant to the focus he wanted to teach others. He has a cool website where talking about his journey. https://alonglegacy.com/
Thanks again for tackling this great and timely topic. It has given me a lot to think about.