When I was 31, my husband of four years, who I loved more than my own life, left me completely out of the blue. We’d had an incredible, epic romance — drawn together like magnets, we married on our third date and spent the years that followed burrowing ever closer together. Maybe that was the problem — I can’t say for sure, because I never got a satisfying explanation out of him. One day I was the protagonist of a Princess Bride-worthy love story; 48 hours later, he moved out.
From the time we met, I had never contemplated the possibility of living without him, and I didn’t want to. I wanted to die for a long time — at least a couple of years. But as I slowly learned to sequester away thoughts of him and the emotions they brought up, I became convinced of a silver lining: The experience would make me impenetrable. If I survived it, I would know I could survive anything, and nothing would be able to hurt me again.
It took the better part of a decade and another deeply identity-shifting relationship, with the man who became my second husband, for me to see that I had it all wrong: Impenetrability means avoiding the parts of life that are most life-like. There’s a reason the visual metaphor for love is an arrow.
The near-fatal catastrophes of our lives don’t always make us stronger. Surviving one hard thing does provide evidence that you can survive other hard things, which is easy to mistake for getting stronger. But in reality they often just make us brittle, make us dissociate and flee from the situations that remind us we can be broken.
Mario Gabriele of the Generalist had a great “50 Things” style post a few months ago that I found myself nodding along to almost the whole way through. The glaring exception was Number 33: “Love is easy. The difference between bad relationships and meeting your spouse is not a matter of degree, but category. Compatibility is unignorable and effortless.”
I believed this completely, once. I’ve since come to believe that what’s unignorable and effortless is chemistry. Chemistry can be powerful enough to turn your life sideways, but it’s not the same thing as compatibility. Compatibility is litigated on the timescale of years and decades; it’s not a momentary feeling but a description of what happens during an extended course of change. Do you grow toward one another, or do you grow apart? Does the relationship help you move closer to the person you aspire to be?
I “just knew” with my first husband. I wasn’t sure with my second. Four years in, the signs have flipped.
There’s a belief, especially common among wonky types, that you don’t find $20 bills on the sidewalk — if an opportunity were real, someone would have seized it already. This sounds worldly and wise, but it’s actually a form of defensive thinking. It assumes the current way is best, that everything worth doing is being done.
In my experience, this is just false. When I started playing poker, I discovered that physical tells were basically a wide-open field — despite the fact that most pros believed the topic was played out. If you think you see an opportunity others have missed, you should have a story for why they’re missing it, and you should ask around to stress-test that story. But if no one can give you a satisfying reason, don’t assume one exists. Sometimes the answer really is just inertia or fear.
Almost nothing is worth doing “well.” Many things can and should be done to a minimal standard of quality, because anything more is a waste of effort that can be better allocated. The exceptions aren’t things that should be done “well,” but things that should be done to an exceptionally high standard, probably a much higher one than you see modeled by the people around you.
This is not semantics; most people really “do everything the way they do anything” — whether that’s in a low-effort or high-effort way. But the point of phoning it in on a lot of stuff is to save your energy to expend on the 1 in 1000 things that really matter … and then to actually spend it.
A recent example: I decided that I want to narrate my own audiobook for You Can Just Do Things. When I told a friend in the industry this and asked whether they knew any good coaches to work with, they said that hiring a coach wasn’t normal or necessary, because my publisher would decide based on a sample whether I was good enough at reading to do it, and if so give me a producer to work with day-of. But it “1 in 1000” matters to me whether the audiobook is so good no one would ever think of returning it on account of the narration, so I’m not interested in the normal-shaped solution that constitutes doing it “well,” I’m interested in the one that causes me to come to mind when someone asks this question. In this case, that means hiring multiple coaches and practicing for months.
Back when I was more alienated from my emotions, I thought about work like this: You have a budget of energy to spend, and the goal is to efficiently convert that energy into impact. You identify the activity that generates the highest impact per unit of energy, and then you spam that button for as many waking hours as you can stomach. Is it any wonder I was always burning out?
What I failed to understand is that energy is not fixed. It’s dramatically affected by what you choose to do — some activities increase your energy over time, others deplete it. This feels so obvious to me now that I feel kind of stupid including it here, but I know many people (they are endemic to the Bay Area) who still labor under the false belief. Whether you enjoy what you’re doing affects your ability to do it year in and year out, and dismissing this as “selfish” doesn’t make it untrue. As my husband puts it, the best use of effortful motivation is to engineer your life to require less of it.
This line, from Kurt Vonnegut, used to neatly encapsulate the way I understood other people — which is to say, not at all. Trying to figure out why people did what they did, or imagine what they’d do next, seemed like a fool’s errand. I was judgmental about it, too: I assumed this was a problem, not with me, but with everyone else.
I didn’t fundamentally move beyond this belief until recent years, when I came into contact with the Enneagram. I imagine there are other personality typing systems that can do something similar, but the Enneagram was magical for me because it clued me into the fact that people can have very different motivational systems from my own that are still internally coherent and produce good things in the world.
People’s behavior was previously incomprehensible to me because I was imputing my own motivational system to them, trying to figure out what would cause me to act the way they did — essentially, concluding that their actions made no sense in light of my goals. But people have wildly diverse emotional hardware, which determines what’s rational for them. And my particular personality — independent, moralistic, systematic, challenge-seeking, competitive — is unusual, so I was especially poorly placed to measure others by the yardstick of myself.
This shift in perspective was dramatically good for me and for my relationships with other people. It let me see the ecosystem of psychologies as a kind of miracle — wow, it really does take all kinds — rather than a prompt for cosmic horror. And it gave me confidence that, if I invested in understanding people more deeply, they would eventually cease to be total mysteries, prone to bizarre and unreasonable behavior. As far as I can tell, this is the better part of emotional intelligence.
The good version of this advice is: You’ll still have to work at being happy, even if you’re rich. Money in your bank account won’t do it for you, and wealth comes with its own pathologies, like endless status-chasing. But the common gloss — that money stops mattering past some modest threshold — is basically false.
You may have heard there’s research showing money doesn’t buy happiness. That research was explosively popular precisely because it was counterintuitive — it betrayed the commonsense intuition that more money means more freedom, more options, more ability to help people you care about. Turns out it was also riddled with methodological problems. More recent work by Matthew Killingsworth (nominative determinism FTW), using large-scale studies that pinged participants about their happiness at random moments, found steady returns to well-being with rising income, no plateau in sight. The myth persists because it serves a psychological function: It helps people without money feel better about their situation, and helps the wealthy downplay their advantages. But it’s not true.
I used to be horribly judgmental of people who made decisions based on intuition, as in, “I just do what feels right.” And then I noticed that whenever I overrode my intuitions, I made terrible decisions. I hired the wrong people, started projects with the wrong people, dated the wrong people, ate food that made me feel bad, did forms of exercise I found unfun and injurious. I don’t have a satisfying theory for why this is, but I know what happens: When I shift from emotional intuition to a logical story about a decision, it’s much easier for my reasoning to get hijacked by plausible-sounding directives that turn out to be nonsense.
It took me a long time to learn this, and that might have something to do with my training in law and poker. Overriding intuition in favor of explicit reasoning makes sense in contexts that reward systematic rationality, where you will get separated from your money if you count on gut feelings. But most of life isn’t a closed system with enumerated rules and clear outcomes. If you try to explicitly name all the factors that make someone a good friend or co-founder, you might come up with some good indicators, but your crude map will also mislead you about the territory.
This is why “wisdom is knowledge that can’t be transmitted.” Wise people have navigational skill, not a long list of rules.
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