As I end this year, I want to thank you so much for reading. I started this substack as a way to “think in community” — it’s much less fun going through these questions alone. Your email replies, phone calls, and walks have been incredible. If it’s not too much trouble, could I ask for two favors? 1) I’d love to hear what you think tI should cover in my posts next year. 2) Would you be able to share my “best” post with a few friends? I am hungry for more thinking partners.
Charlie Munger recently died at the age of 99. What was particularly striking to me about Charlie Munger, all of his investment success notwithstanding, was his endurance. After he graduated law school at the age of 24, Munger kept working until he was 99, most recently republishing his book just a couple weeks before his death. How did he sustain his energy for so long?
I’ve been thinking a lot career longevity lately. I'm only 10 years into my career and already want a break. Many of my friends feel the same way. There’s a trend of “taking work sabbaticals” in the industry, and I see a tweet or a LinkedIn post about a prospective sabbatical almost every week. These messages have a few common characteristics: they’re from a technologist (never a doctor), they’re an employee of a firm (usually of a few hundred people), and they’re interested in spending some time exploring new ideas before taking their next role.
It’d be one thing if everyone decided that they’d made their money, and it’s time to live off the land. Or that ambition is an illusion, and it is now time to be an ascetic in order to achieve nirvana. But most of these people are wildly ambitious despite their break. From my perspective, I like technology. I want to build something creative and great. My ardor has not flagged; nor has my ability to grind. Yet, there’s something calling for a break.
It feels like we’re in the story of the tortoise and the hare. In the story, the hare and the tortoise decide to race. The quick-moving hare gets a big lead and takes a nap along the way, but oversleeps. He ends up losing to the “slow and steady” hare. You’re supposed to aspire to be the tortoise so that you can win in the end. Yet until now, I have been like the hare – maybe not in the objective speed of my career, but certainly in how tired I currently feel, catching my breath by the side of the road, waiting to figure out the direction I should go next.
Of course, the ideal is a “well-paced hare’s” career – a hare trained by Kenyan marathon running coaches who knows how to win and knows how to self regulate. However, as I’m always reminding myself, it’s more useful to wish for “training” over “talent.” Therefore, I’d like to be a steady tortoise. Like the steady tortoise, I know I want a long career that is filled with curiosity and energy. I know that great things take time, and I want to have the endurance to last that long.
I don’t have any of the answers to what endurance might look like, and it’s as broad a question as anything else I’ve asked before. In Munger’s case, it seems like endurance can come from emotional management, a balance between exploration and “exploitation”, and focusing on velocity instead of speed.
Emotional Management
The hardest part of managing my career has been managing my emotions. It’s not the labor that exhausts me, it’s the feelings. When I am happy and fulfilled, the hours do not matter. When I am feeling interpersonal stress, powerlessness, or self-doubt, I feel the tiredness seep into my bones. My lowest moment in my career was when I was working 6 hour days, sneaking out of the office every Friday at 2, but fighting with my manager the entire time.
Endurance, in contrast, requires putting work travails into perspective and handling them with equanimity. It requires that you can treat the highs and the lows with calm optimism and remove the emotional biases from getting in the way of rational decision making. Corporate politics didn’t go your way? Let them go. You didn’t win that sales deal today? Limit your worry to the real action that you can take to fix it, not the unproductive tossing and turning. Passed over for a promotion? Stop letting it eat at you while you’re brushing your teeth. Some people have this ability naturally, and work’s stresses are something that they can easily channel productively. They play a hard game in the office, but never take the game’s score home with them at the end of the day. They know that the “worry” you take home is genuinely counterproductive because it gnaws away your insides.
For the rest of us mortals who aren’t born with this self regulation, Charlie Munger suggests two other factors highly correlated with fulfillment and equanimity:
Have children
Find religion
In his last-ever podcast with John Collison, he says:
John: [00:40:01] Why do you think the people who have kids at 21 were happier?
Charlie: [00:40:04] It's very constructive to help other people and everybody feels pretty good about his own children. To have a lot of responsibility and bear it well, I think helps people. If you take the philoprogenitive people, say, the Mormon church, really still have the big families. If you measured human felicity in some objective way by measuring time spent smiling versus time spent frowning, the Mormons would average out way happier than the general population.
My theory is that we live too unmoored from things that matter. We let the bullshit bother us. For those of us not blessed with secular Buddha-like detachment, family and religion are cheat-codes to give you mooring. They help buffet (no pun intended) the waves of feelings that emerge from doing hard things, enable you to better forgive yourself for mistakes, and help you accept the things that you cannot control. Munger is devout, had four children before he was 29, and sadly had a child die at the age of 8. Having these belief systems and responsibilities are not a cure-all for workplace stress, and I’m not at all saying that everyone believing in religion or having children is good for the world. But it can help with managing emotions at work, having an important non-work purpose, managing moral ambiguity, and taking a long term view.
Balance exploration and exploitation
Most of my friends, myself included, are taking sabbaticals after careers in high growth technology companies. Within these companies, it was hard to indulge in personal curiosities. Work needed incredible focus on specific areas and ate up all of the time. In some ways, that focus was very energizing: I could apply myself narrowly, gain expertise, and see the fruits of that effort. Yet, once you have depleted your reserves of ideas and creativity, nothing other than letting yourself just indulge your curiosity will restore those reserves.
Startups are especially prone to creating this sense of urgency to capitalize on near term opportunity without any exploration. At Stripe, because there were new business opportunities scattered everywhere like diamonds on the ground, exploring the unknown was really hard to justify in the pursuit of efficient corporate profit. At Watershed, the business needed execution on the core product more than it needed any distractions with new areas. Many companies are very poor vehicles for curiosity, especially if you’re not in a “research” shaped role.
Sabbaticals are attempts to satisfy the desire. I get to be my cringiest self. Every day, I read books, talk to interesting people, call up my friends, and exercise. I get to write a few posts a week about ideas I’m interested in exploring. I take trips with my friends. I am learning about everything from game design to Korean language study.
To reap, you must first sow. Exploration is undervalued and can be discounted as dabbling. But it has a funny way of paying itself back in unexpected ways. When my college professor met Bill Gates for the first time, he described his work as “using the manufacturing tools of the computer industry to make vaccines.” And when Bill Gates pressed further, Joe DeSimone explained the full story – that while developing polymers for lithography for patterning silicon wafers, he realized, thanks to some crossover work he did with a medical professor friend on sabbatical, that the same techniques could be used to improve delivery of nanoparticles in medicine. His dabbling in new fields helped him discover one of the first huge breakthroughs of his career.
On the other side, endless exploration is equally exhausting. It can feel meaningless to wander through a sea of ideas without sinking your teeth into anything that can produce results. Some people get addicted to the exploration pursuit, and truly become dilettantes. Knowing the point to stop exploring is a hard judgment call – your own “exploit versus explore” tradeoff.
When I look at successful and tenured people who have endured in long careers, I can see these distinct “explore” versus “exploit” phases in their career. Munger was a real estate lawyer, an investor, and at times a writer or architect. My mom is a middle school math teacher who has taught for 30 years – her work is all about going out, finding resources, and making things happen in a fairly structured and consistent way. To satisfy her desire for exploration and renew her enthusiasm for her work, she took two years off to start and run a dance company. And after serving as the zany sponsor of GoogleX for many years, Sergey is apparently back in the fold of core Google engineering, coding furiously in the trenches, to help Gemini meet its goals.
Velocity, not just speed
Ideally, the tortoise begins the journey at a steady clip, with a map of the trail, and an excellent sense of how to keep itself on track. But if that isn’t the case, a good reason for the tortoise to pause is if it doesn’t know the way. Rather than wandering aimlessly, a focused moment of determining the next direction of travel is vital.
My physician siblings don’t need these orienting breaks, even though their work is exhausting. They lead extremely structured and tracked lives, with a very limited set of options at each branch of the tree. They know if they can push through 10 years without breaks, they’ll end up in their chosen end destination. In contrast, technologists take breaks in careers in technology because there isn’t an explicit track. The world is changing so much – will software development even remain valuable? Is AI taking over? – that constant calibration on direction matters as much as speed and force. I can work incredibly hard, but if I’m not thoughtful about what I’m trying to do, what I care about, where there’s benefit for me, I won’t be able to succeed.
I think a carefully chosen direction with minimal “rerouting” points is vital to experience the benefits of compounding. This was obvious when I was at one company — I could become better and better with much less effort than my newer peers due to my company experience advantages. I could invest in years-long threads. Munger did this over 74 years with very consistent partners and mental models. His excellence in part was due to the benefits of compounding in his chosen path and in his chosen relationships. It makes it easier to endure.
Endurance is rare.
Endurance requires something strange: hard days but a good life. Good lives are rare. Good days are easy to come by. We can always find an easy weekend after a week at a mediocre job, a day in retirement that seems just fine, an extra hour of sleep. Instead of a life looking for fleeting good days, I’m willing to make a tradeoff for a good life. I know that struggle is hard, that endurance doesn’t come without a meaningful cost. But it seems worth it.