Turning 40 is a milestone that should come with a manual. It doesn’t, of course, but it does come with a decade’s worth of receipts for lessons learned the old fashioned way.
As I ponder the next decade ahead of me, I’ve been reflecting on the things I picked up in the last one that have shaped my understanding of people and the world around me. I share seven of these lessons in the hope they might be helpful to — or at least amusing to 😅 — the reader.
1. You Don’t Know Where You Rank in Someone’s Priorities Until You’ve Seen Them in a Crisis
It’s easy to be a good partner during the good times.
The real test of character comes during the bad times. It is only when the pressure is on and pleasantries feel like a wasteful luxury that people reveal their true priorities — and, especially, where you rank in those priorities. It’s in those moments of crisis that you can see who someone fundamentally is.
This advice applies to both love and business: if you can, don’t enter into a partnership — getting married, starting a company together, having a kid together — with someone until you understand how they handle crisis. How do they act when they’re scared, angry, or cornered? Do they collaborate with their partners, or do they retreat into self-preservation? Do they treat partners like equals or burdens? Sources of strength or resources to be exploited?
I’ve sadly learned several times in the past decade how people who are giving and collaborative when things are one way can quickly close off and prioritize themselves when things got tough.
To be clear, this isn’t to say people who react poorly under pressure are “bad” or deserve to be cut out of your life. Crises are difficult for even those with the strongest of moral character, and you can still have a friendly or productive working relationship with someone who doesn’t consider you one of their top priorities.
But understanding how someone acts in a crisis is a vital data point I would recommend thoroughly understanding before entering into any kind of serious partnership.
2. Profession can be an Oddly Good Read on a Person
I used to hate the question, “So, what do you do?”
It felt reductive, and almost insulting, especially when I was starting out in my career and my job was only a very small piece of what I felt I had to offer.
But I’ve come to appreciate that while a job is never the whole story about a person, it can be an incredibly revealing chapter. When you spend most of your waking hours on something that also shapes your finances, social status, and daily challenges, it inevitably molds you. Jobs define our incentives, hint at our training and skills, and frame our definitions of success and failure.
Knowing someone is a practicing doctor in the US, for example, gives you a hint about their:
- age & education — given the amount of medical training necessary to practice medicine in the US
- their income — likely relatively high, with more precision possible if you know their specialty
- a sense of their views on the US healthcare system — I’ve never met a physician who likes the health insurance companies who impose rules and paperwork on them to get paid, their electronic medical record system, or medical malpractice lawsuits
- their approach to risk — having being ingrained in the ethos of “first do no harm”
- their views on credentials — given the amount of time (and money!) they spent on getting their Medical Degree as well as the additional licensing and certification necessary to practice
You won’t always get every detail right — and profession won’t give you a good indication on many aspects of their personality or personal lives that have little to do with their career — but it’s a more useful than not set of heuristics for understanding the people you meet.
This is why I’ve grown very wary of interfacing with politicians. To succeed there requires a level of self-obsession that’s hard to square with sincerity. Success is driven by saying what’s popular, not necessarily what’s true (or even what you believe). Politicians with any level of success are also surrounded by people paid to flatter them. It creates a backdrop where genuine connection is difficult, power dynamics are twisted, and relationships easily become transactional. Andrew Yang captured some of this in a piece he wrote for Politico Magazine in 2021 entitled “When I Ran for President, It Messed With My Head”.
Of course, there are exceptions. But in my experience, it is foolish to underestimate how influential the incentive structure of a career can be.
3. There’s Little Upside in Talking About Politics
To start with the obvious: policy matters. It shapes our lives, and in a democratic society, ignoring it is irresponsible.
That said, I suspect many of us engage with politics far too much for our own good. The problem is that modern political discussion and news isn’t about logic — it’s about evoking visceral, tribal outrage. This is bad for two reasons. First, it leads to bad policy — it makes us seek symbolic victories and “cultural” retribution rather than nuance and sustainable compromise. Secondly, it leads to bad behavior by training us to see the world in terms of “us” versus “them.”
In my 20s and early 30s, I loved a good political debate. I had a neat little box of “obvious things all reasonable people should believe.” That argumentativeness and certainty cost me. A long time friendship ended abruptly this past decade, likely over some position I took in one of those debates (it was never entirely clear to me). I also nearly became unfriendly with a former mentor over a political disagreement over that “neat little box of obviousness”.
As someone who values his relationships, these were not proud moments. And it led me to ask: what upside did I get from seeking these debates? A temporary satisfaction that “I am more righteous than the ‘other tribe’”? Scoring some kind of rhetorical point? Hardly seems worth it.
I now try to disengage from the daily outrage cycle of political news and who-said-what. After all, it rarely has real impact on policy, and the news cycle usually moves on after a few days. Instead, I try to focus on tracking substantive policy changes and analyses. It’s a lot more boring, but that’s a feature, not a bug.
I also am a bit embarrassed to admit but I now actively avoid discussing politics with people — both online and in real life. This isn’t to say that I don’t have my own opinions (and in moments of weakness, I’ll share some of them on social media), but in recognizing there’s little upside, I’ve come to realize nobody really cares what I think. They just want to know if they should get angry with me or at me, and I don’t see the point in playing that game any more.
4. Embrace the Unlikely
If my 30s taught me anything, it’s that the improbable is inevitable. In the last decade alone, I experienced things that I thought were highly unlikely to happen in my lifetime:
- was fired
- called as a witness in legal proceedings (twice!)
- lived through a global pandemic
- saw a vaccine developed in under a year
- saw US inflation go above 9%
- watched a massive political re-orientation on globalization in the West
Statistically speaking, over a long enough horizon, unlikely things will inevitably happen. But, beyond that, because unlikely things are highly correlated with one another, unlikely things will likely happen together. In my list above, for example, at least 3 of those things are directly related to COVID.
So, what do you do in a world where the improbable is not only inevitable but will likely co-occur?
First, prepare where you can. Get an estate plan, a rainy-day fund, a diversified portfolio, and make contingencies.
Second, and most importantly, try to embrace the unlikely. The chaos of 2020 was a period of great stress for me and my family. I remember wondering at points if this was the end of the global economy and of in-person interaction. These are especially unsettling thoughts when you have a toddler at home and weren’t sure when you would next see your aging parents.
But, in hindsight, 2020 was also one of the most transformative and productive years of my professional life. I helped build a telemedicine operation (that is, as of this writing, still doing pretty well); learned how to code AI models and had some of that work ultimately published in peer-reviewed journals; and tried my hand at policy work which led to new friendships and professional opportunities.
Out of that tumultuous year came something positive that, I have to admit, would not have happened otherwise. So while 2020 was a terrible year in many fundamental ways, I’m grateful I was in a position to embrace it as an opportunity.
5. Genius Doesn’t Generalize
Smart people tend to be smart about multiple things. So it makes sense to seek out the advice of people who know better.
However, we live in an age of unhealthy hero worship powered by influencer marketing and interview podcasts. We assume that because someone is brilliant in one domain, they’re worth listening to in others.
But, in my experience, nothing could be further from the truth. What it takes to achieve genius-level mastery in one area often comes at the expense of others.
I’m always baffled when people ask Elon Musk for life advice or Warren Buffett for his opinion on anything besides investing. A quick read of their biographies shows that their personal lives are a mess. Their genius is highly specialized. Their situations are extreme. At best, you get a different perspective. More likely, you hear something that is likely completely irrelevant to you.
It’s worth remembering this the next time you hear a billionaire investor weigh in on sociology, a Nobel Laureate scientist weigh in on politics, or an author of fiction weigh in on technology. It’s far more fruitful to consult a few smart friends or read about actual expert opinion than to mind the opinion of a famous (and/or rich) person on a topic outside their expertise.
6. Good Taste is Overrated
In our careers, “good taste” is something worth cultivating and investing in. It signals judgment and makes you hard to replace, especially in this new world of AI.
But in life? I’ve come to a radically different conclusion: it’s much better to have low standards.
My inability to distinguish a $20 bottle of wine from a $200 one means I can get the same pleasure from wine as a world-class sommelier for a fraction of the cost.
My love for bad action movies and rewatching sitcoms means there’s always something to watch on an airplane.
My willingness to enjoy fast food means I can find a decent meal almost anywhere in America.
I used to be slightly ashamed of all of these things as evidence of my “uncultured palate”. Now, I see it as a gift. Being easy to please is a superpower for everyday contentment. And, it frees up time and mental energy to focus on what I can discern and care more about.
7. Play Stupid (Status) Games, Win Stupid Prizes
Many things we pursue in life aren’t for a tangible reward, but to signal something about ourselves to others and (sadly, often) to ourselves. These status games are everywhere, and the trap is that you can never win. There’s always a new car to buy, a more exclusive vacation to take, a new trend to follow. Marketers are masters at playing on this to keep us on the never-ending spending treadmill.
I felt this most acutely in the past decade with my kids. The entire “new parent industry” is a masterclass in exploiting a new parent’s desire to be a good parent. It’s engineered to make you feel guilty for all the things you aren’t doing (and all the products you aren’t buying) while feeling proud of the things that you are (and all the products you are buying). I remember the shame and anxiety when our eldest son didn’t seem to be hitting his speech milestones as quickly as the books suggested (or *gasp* as my friends’ kids were).
Thankfully, my level-headed wife and pragmatic pediatrician helped me see the bigger picture: our son was happy, healthy, and developing just fine on his own timeline. And sure enough, he started talking up a storm at two-and-a-half and was reading full books not long after.
This sort of un-grounded status seeking is everywhere: people staying in “prestigious sounding” jobs they hate, spending money to keep up with their friends’ Instagram lives, or chasing exotic investments just so they have a more exciting story to tell than “I just buy index funds.”
The lesson isn’t to drop out of all status games: that’s probably impossible. I will sheepishly admit I buy high-end gadgets not because I need them but to signal that I’m the type of person who buys high-end gadgets. I’ve also maintained a ridiculous 425-day+ Reddit streak for reasons I can’t particularly defend.
But, the lesson is to be deliberate. Recognize a status game for what it is, and then consciously decide if it’s one you actually want to play.
Seeing Past the Surface
Looking back, if there’s a single thread connecting these seven lessons, it’s about learning to see past the convenient surfaces. It’s about understanding the hidden incentives that drive people, the true priorities that emerge under pressure, and the surprising freedom that comes from ignoring the ones that don’t matter.
This process of looking deeper is never really finished. The biggest thing I’ve come to appreciate is that the learning never stops. I’m sure my 40s will dismantle some of the certainties I’ve built in my 30s, and I can’t wait to see which ones.
That, I suspect, will be the real adventure.
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