Twenty Things I Learned in My Twenties

Some good old-fashioned advice

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I turned thirty last month. Here are twenty lessons from the preceding decade.

1. “Quality” is usually just quantity in disguise.

“Quality” here is a flexible word which can be understood as “talent,” “success,” or “excellent work,” depending on the context. The key point is that whenever you find yourself asking How did they do it!? the question often obscures the banal fact that they simply put in a large volume of reps or hours, or made ten bad versions of whatever it is they are ultimately known for—and you just happen to be looking at the one time that worked.

Put another way: When the field is competitive and success is probabilistic (which success always is, to some extent) you have to get more shots on net. No individual attempt is likely to work out, but if you make persistent and reasonable bets, chances are good that one of them will eventually hit. This is true for job applications, for venture capital, even for love. (Corollary: if your rejection rate is zero, you’re probably not being ambitious enough.)

Similarly, I’ve come to view creative work as much more Darwinian within one individual’s process than you might imagine looking at the end result: What looks like genius is in fact excessive generation followed by intense selective pressure. (This post could well have been titled “Forty-odd Things I Learned In My Twenties, Culled Down to the Twenty Best Ideas.”)

2. In housing, you’ll habituate to everything except light and noise.

When you’re looking for an apartment, it’s easy to become enamored of the features that are easiest to see: countertops, closet space, in-unit laundry. These features do matter on the margin—but after living in several different buildings over the years, I can say with confidence that you adjust to them very quickly.

However, there are two factors which you will not adjust to—factors which permanently affect your baseline happiness: light and noise. If the space you’re considering is in a dank basement, or if you hear motorcycles blaring on the street at all hours, proceed with caution. If you have to compromise, compromise on the dishwasher, not your happiness or sleep.

3. You can learn just as well without a course or grades.

If you’re in school or recently graduated from it, you’ve likely internalized a model of learning which is in fact quite contrived: that assignments should be well-defined in advance; that you will get an unequivocal score on their success; and that the longest project one could possibly undertake lasts no more than six months. You may not consciously endorse these beliefs, but your entire educational career has reinforced them, and it can take a while to find another way.

By contrast, as an adult, you often need to find or create your own “assignments”—which can extend for many years—and typically get ambiguous data back as to how successful they were. This, in my view, is actually a good thing: It forces you to think more critically about self-improvement than a one-to-a-hundred percentage ever could. Rather than relying on an external authority to manage and evaluate your progress, you might think of yourself as an athlete or musician—or better yet, a scientist. The ultimate “grade” of your performance is simply whether you made the goal or flubbed a note; whether, when you test a hypothesis, the results seem to support it.

4. Throw out your bad pen.

This is an idea I stole from Kevin Kelly, who advises: “Take notes if you find yourself wondering ‘Where is my good knife?’ or ‘Where is my good pen?’ That means you have bad ones. Get rid of those.”

A “bad pen” is, I think, a kind of metaphor—and a flexible one at that. Most straightforwardly, it means you shouldn’t settle for something sub-par when you could easily do better. To me, it especially serves as a reminder to recognize when something which feels like it’s part of the environment is in fact entirely within my control. I’ve often caught myself thinking thoughts like Wouldn’t it be nice if people talked on the phone more? or My friend group should do more random activities! only to recognize that there is in fact no great skill required to call someone on the phone or organize a trip to the aquarium.

Put another way: You don’t need to wait for permission or to be exhorted to take action, or to get so disgusted with yourself that you make a change. You can just fix what isn’t working!

5. If it feels like you’re facing an insurmountable problem, you probably need to eat, sleep, or go outside.

Your present state of mind is never explained by one single cause; it is multidetermined, an emergent property of many different physical and psychosocial factors. Often in the heat of the moment, we default for proximate psychological factors for why we feel shitty when really a stronger contributing factor is that a basic physical need is not being met. Furthermore, even when you are facing a serious problem, you’ll be much better equipped to fix it if you address some of the other subcomponents of your misery.

6. For job satisfaction: colleagues > day-to-day work > mission.

I should caveat this by saying that of course all three of these matter, and that I feel fortunate to be in a role now where I have all three. But I’ve worked different jobs earlier in my career where the balance was off. In retrospect, part of my problem was a misperception of what would actually make my work enjoyable. The truth is, the greatest mission in the world can only go so far when your day-to-day is tedious or stressful; and even relatively menial tasks can become quite engaging when you’re doing them with the right people.

Unfortunately, in this ranking, the most important factor is the least legible from the outside, and vice versa. A mission you can read on the company website and the day-to-day you can get a decent sense from a job description, but you won’t really know the people until weeks or months on the job. Still, do your best with the information you have, and if you have to make tradeoffs, this is how I think you should prioritize.

7. Low sticker prices often obscure hidden costs.

A couple summers ago, I rented out a storage locker in Brooklyn to store my electric bike. I found a place near my sublet that seemed unusually cheap—a mere $25 per month, when the next most affordable option was at least double that. I booked by phone, and when I arrived the next week to drop off my bike, an employee told me the number of my storage unit.

From there, my girlfriend and I went up to the second floor of the building, where we found a warehouse full of metal cubes. But as we walked up and down the aisles, we couldn’t find my unit anywhere. Eventually, my girlfriend spotted it: There was a second level of smaller storage units in the crawl space above the main ones, and my locker was one of these.

In the end, to get my e-bike into storage, we had to wheel a rickety metal staircase over and haul the bike up ten feet to the crawl space. In the course of moving the staircase, I scraped my hand against a metal door and gashed it open; and when we finally got the bike up to the top of the ladder, it was just too big, so I had to carry it back down the staircase and remove the front wheel. As I hoisted my partially disassembled bike up the steps a second time, the staircase wobbling beneath me, blood gushing from the fresh wound on my hand, it occurred to me that maybe, just maybe, it would have been worth it to pay an extra $25. (My girlfriend endorses this message.)

My point isn’t that you should never go with the cheapest available option—just that, if you do, there’s a much higher probability you’ll have to pay for that choice in time, inconvenience, or unreliability. Think carefully about whether that risk is worth it in a given situation.

8. If anything, you’re probably being too persistent.

Our culture bombards us with messages like “winners never quit” and “never give up.” This is a shame because it is arguably the opposite of what many of us need to hear: To a greater or lesser degree, all of us have a natural bias against changing course.

The truth is, there is a massive opportunity cost to seeing through every undertaking you begin: Each minute you spend with a book you hate is a minute you could be reading another one, and each year you spend in a bad relationship is a year you could be dating someone else. Sure, it’s possible your powers of selection are so perfect that everything you start is truly worth finishing, or that if you grit it out with a bad experience you’ll eventually turn it around—but I don’t think these are generally good bets. Most of us should be striving to quit earlier and more often. (For a smart and accessible elaboration on this idea, I recommend Annie Duke’s book Quit.)

9. Charge your phone outside your bedroom.

If an alcoholic wanted to sleep with a bottle of vodka on their nightstand, would you think that was a good idea?

10. Kindness is strategic, and usually positive-sum.

Like many young people, I absorbed from college a kind of kneejerk cynicism which assumed that anyone who accumulated wealth or power necessarily did so by exploiting others. To improve society was to resist these forces of oppression by any means necessary; cooperating with political opponents was suspect at best, genuinely trying at work was self-exploitation, and displaying sincerity was outright cringe.

To be sure, power often has to be held to account, and indiscriminate trust is a bad idea—but I’m now more sure than ever that treating high-stakes interactions as adversarial is a losing strategy. If your default theory of change is it derives from conflict, your model of the world has a huge hole in it: In general, people prefer to help people they like, and you’re much more likely to persuade others if you are yourself persuadable.

A key reason this is true is that in many relationships and negotiations (especially over longer time horizons) one person’s gain is not the other person’s loss. When you give a friend a lift, they save money on an Uber—and you get to call in a favor in the future. When you’re genuinely invested in helping a customer, your company benefits—and your work becomes more enjoyable/professionally valuable. When you give a well-earned compliment, the other person feels good—and you reinforce behaviors that you want. These kindnesses cost you little or nothing to give, yet they often yield outsized rewards over time.

11. That you said something is often more important than how you said it.

Most day-to-day communications serve a social function: While you can earn extra credit for crafting the perfect event invite (or apology text or thank you note, etc.), the truth is, these kinds of messages tend to be graded pass/fail. The impact derives almost entirely from the fact that you want them at your party (that you have remorse for your actions, that you recognize their effort, etc.)—not your perfect prose. 

There are certainly exceptions to this rule (eulogies, lyric poetry), and of course tone and word choice will color how the message is received. But if you find yourself endlessly tinkering with a communication that is, at core, a means to a social end, then don’t sweat it too much.

12. Say it again better.

Furthermore, if you find that your message falls flat, don’t panic! Most hard conversations are—almost definitionally—conversations between two people who have a lasting relationship; this means there are always opportunities to soften, caveat, or clarify what might have originally come across as blunt or awkward. Again, if you find yourself tied up in knots looking for the perfect words or moment to express yourself, consider the possibility that it is not one hard conversation but the first in continuous conversation with many installments.

13. Figure out what time of day you work best, and protect it fiercely.

For me it’s the morning. For others it’s late at night. I suppose it’s theoretically possible there are people who experience a surge of focus in the middle of the afternoon, but I can’t say I’ve met them.

14. When you acquire a new article of clothing, get rid of an old one.

Similarly when you acquire a knick-knack or swag from some event you know you’re going to eventually dispose of, just toss it right away. Active purging systems like this will prevent you from accumulating lots of crap on top of the crap you already own (or even better, prevent you from acquiring more crap in the first place).

15. Consistency trumps intensity.

This is a theme I’ve written about recently and often, including the empirical evidence for it. (You could even say I offered a version of the idea at the top of this very list!) Still, it’s worth rehashing some of the reasons why it is that regular incremental progress is generally better than high-intensity spurts.

Of course there’s the obvious and banal fact that moderation is less likely to produce burnout: Much better to jog for ten minutes every day for a year than to run a single marathon and quit. But I also think people underestimate the extent to which skill is an investment, and regular practice compounds in a way that big one-off “deposits” can’t make up for. The human mind is an incredible pattern-finding machine, and it feeds on repetition; each time you activate a schema or set of ideas—even briefly—the machine grows more powerful.

16. People don’t care how smart you are; they care how smart they are.

It’s easy to leave school (which rewards you for shooting up your hand in lecture, and bubbling correct responses on multiple-choice exams) believing that the world is intensely interested in your innovative solutions, or your ability to recall information. Those skills are also valued to some extent in many adult contexts. However, in general, people are far more invested in ensuring that they don’t look dumb, and that they get to contribute their great ideas. Try affirming good points, and asking genuine questions.

17. Confidence follows practice—don’t wait until you’re “ready.”

Wait until you feel like you’re almost ready, then just start doing whatever it is you’re hoping to achieve. In retrospect, you’ll realize you were readier than you imagined.

18. Don’t assume you know what caused a fuck-up.

In many workplaces, there’s a meticulous neutrality of language embodied by phrases like “It is my understanding that blah blah blah.” and “Can you clarify whether such-and-such is done?” I used to read these phrases with an eye roll, believing they were passive aggressive substitutes for blame. Still, mostly I held my nose and adopted the lingua franca.

At a certain point, though, I started to notice a funny benefit to this ostentatiously neutral style: A significant portion of the time (maybe around a third?), it would turn out I was in some way wrong or misinformed. The email confirmation I was “just checking on!” was revealed to be sitting in my own spam folder. Or the decision I “could be mistaken, but thought we’d agreed to…?” turned out to have been misremembered. Whenever exchanges like this happened, I’d think to myself: Thank God I didn’t send the curt version, or I would really have egg on my face!

Interestingly, if you err toward this value-neutral communication style, it eventually begins to infuse the way you perceive the world. Now, even when it seems quite likely to me that someone else has messed up, I usually have the presence of mind to recognize that there could well be a big piece I am missing. And what’s really gained anyway by assigning blame anyway? After all, when it comes down to it, everything you know about the world really is just “in your understanding”—not objective reality.

19. A “good rule” that requires immense effort to enforce isn’t actually a good rule.

This lesson is one I learned the hard way teaching high school when I created a “simple” late policy whose only downside was that it required constant judgment calls and considerably more math than any English teacher ought to endure. As I iterated on this original policy, I eventually developed a better one which, while slightly legalistic and more complicated to explain to students, required minimal brainpower to actually implement. I strongly recommend the latter approach over the former.

(Some cousins of this idea: If there is a situation you know you’ll face repeatedly, invest some time up front to figure out how you’d like to respond rather than improvising every time. And a good productivity system or workout routine is the one you actually stick to.)

20. Energy is a weather system, not a fuel tank.

This lesson comes, like so many great ideas of our time, from the platform formerly known as Twitter. The whole thread is worth reading, but here’s the key quote:

After years of floundering, I think I'm finally getting it: You get energy by spending it. The fuel tank metaphor is completely misleading. The body supplies energy to meet demand. The tank *expands* if you use a lot of fuel.

The core insight that energy expands the “tank” rather than draining it is, in my view, extremely useful. After all, if you’re too bought into the tank metaphor, you’ll risk stopping projects short just when you’re getting into flow, or you’ll be confused why you don’t feel refreshed after sitting on the couch all day and eating popcorn. But of course there are limits to the alternative as well: Everyone needs to rest eventually, and energy can’t expand infinitely.

I’m not sure what the best alternative to the fuel tank metaphor is, but if I had to offer one, I might suggest a weather system, or perhaps some other natural phenomenon. I like this analogy because it accurately suggests that on the local level, energy does frequently feed on itself: Hot days tend to be followed by hot ones; hurricanes build, swirling faster and faster; but eventually heat waves do break, and storms blow themselves out.

The upshot here is basically not to overengineer the way you move through the world: Push yourself out of your comfort zone—but not too hard—and if it’s going well, keep going; follow the natural rhythms and seasonality of your body.