Turning points


Something I've been thinking about lately is this idea that persistent failure can be much more impressive than success.

There's one piece of this idea that's about what poker players call “resulting”, evaluating a judgement or action by its outcome, ex post, rather than what could have been known at the time, ex ante. It's easy to pay too much attention to end results and ignore the importance of strong decision making with limited information.

But there's another, complementary, piece to this idea of being impressed by failure: most people do overindulge in resulting, and they worry too much about superficial “wins” and avoiding losses as a result. Persistent failure in a single area is a high signal indicator of someone breaking from this trend in a way that persistent success can never be.

Someone on a lucky streak in life and put off thinking about their real goals or desires for a long time, because they'll get a lot of external encouragement to just keep doing whatever it is that they're doing. Someone who gets a series of bad breaks has the exact opposite experience: not only do they deal with the personal sting of their setbacks, but people around them are likely to lose faith in that person as well. Bad news can always keep coming, and the person on the wrong end of it faces uncertainty about the future, personal disappointment, and strained relationships all at once. That person does not have the luxury of not knowing what they want; their willpower is being ground to dust as it is.

There are trivial cases in which persistent failure is unimpressive, of course. If you make a hobby of consistently attempting something—running a sub-3 hour marathon, say—but then you never make any concentrated effort to improve—e.g. you go jogging but never follow a real training plan—then you can conceivably “fail” and, by not really trying, further fail to gain anything of substance from the experience, either. But examples like that kind of prove the point: is your goal really to run a great marathon, or is your goal to get exercise and enjoy a sport in a semi-structured way? After 5 or 6 years of attempts, I'd expect most people would either admit to the latter or finally get serious about the former.


Dan Luu has a great essay noting that “95th percentile isn't that good”, which feels related here. Most people don't seek out feedback on things they're trying to get better at; more generally, most people don't take the time to make a plan for how, procedurally, they can improve at the things they care about, other than “do it a lot”. That might seem like another way to be unimpressive in persistent failure, but I'd argue for a different take: raw determination can let your surpass an overwhelming majority of the active practitioners of a skill. Adding a bit of cleverness to that seems easier (and maybe more potent) than the other way around.

One thing I routinely tell ALF grant recipients: all successful people have some part of their personality that is inherently uncompromising. It's something that structurally needs to be there, a backstop of stubborn determination that can be relied on after life has ground down the more elegant parts of you.

Finding that part of yourself is usually synonymous with finding what you really care about in life. When you find something you care about enough that you can keep failing at it indefinitely, you'll usually find a way to turn the narrative around eventually.

The techniques vary from activity to activity, goal to goal, but the general shape is the same: you get a bit more mindful of your daily practice, you solicit more feedback, you find ways to assess and reflect on your own performance, you study the greats in the field, all the etceteras.

Eventually you start thinking about the full sum of your personal experiences and look at what makes you different as a possible source of strength. Going from track & field to football sucks when you can't take a hit, but pays off when you can dust any cornerback; moving from practicing law to software engineering can feel like a huge career reboot, but you'll be a lot more diligent than any of your peers; stories like this happen over and over, taking many guises and appearing in many settings.


As someone whose career rests on architecting complicated software to do complicated things, I would say that most of life is not, in fact, that complicated.

Life isn't complicated. Life is hard. When people try to make it complicated, they're trying to avoid the inevitable part where it's just hard instead.

It would be much easier if we could find a way through the world where we never faced prolonged setbacks, every defeat was followed by a winning streak, and every disagreement was, in the end, resolved happily. I don't generally believe that's possible, though.

Some people try to chart convoluted paths that avoid any chance of backtracking, but they mostly sit still with their plotting, going precisely nowhere instead.

The simpler solution is generally the better one. Accept losses as inevitable in every game worth playing; accept failure, even many failures, as the price of every success; accept that most people won't believe in you when it's not convenient to do so, and fight to hold onto the ones that do.

Find something you can really believe in even when the world's moving against you. Cherish it; nurture it; build yourself back up; get smart; play the long game; play to win.

Everything worth saying here has been said countless times before, because it's all still true. We say it again anyway, both as a way of reaffirming the truth and as a way of reflecting on how we've embodied these greater themes.


I started a new job last week. I'm excited about the role but don't have much to say on it yet.

This essay is about new beginnings, Independence Day, and a complicated question about romance I can't pin down with words.