Apology of Failure, part 1

Success needs no press agents. Nobody has to convince you of the attractiveness thereof; the fruits of success are enticing intrinsically. You could attain fame, fortune, and maybe even the ability to rub it into the faces of the doubters. Indeed, a slim ray of hope is often all it takes to coax a man into action. There are a billion and one books on the market about successful people, be it businessmen, political figures, scientists, writers, artists, etc. and for good reason: nobody wants to read about the life story of some homeless bum wandering the streets of San Francisco. Even my namesake is, in my humble opinion, the most successful person who ever lived.

“Why then,” you ask, “are you writing you inaugural a post about failure? Nobody wants to read about something so uncomfortable!” When someone successful is being interviewed, they’re always asked about why they are successful but rarely confronted on projects they’ve failed but learned from or times when they had to abandon something that they’ve sunk a ton of effort into. That’s exactly why I write about it – while not everyone will be massively successful in their life, we’ve all experienced failure. And thus, I assert that knowing how to handle and even embrace failure is just as critical as knowing the formula for success. The pathological avoidance of failure is a huge disservice to not just individuals but also to humanity as a whole.

I’m going to keep the platitudes to a minimum. Everyone knows those annoying truisms plastered around the walls of your typical American public-school classroom, and nobody ever pays them any heed for good reason. Quotes without context, application, and rationale are meaningless. Now put away those champagne bottles and grab your coping liquor of choice – let’s talk failure.

Now, it would be improper of me to begin a discussion of a topic without first conceptualizing it. First, what do we normally think of when we hear the word “failure?” Words like “stupidity,” “incompetence,” “self-doubt,” “worthlessness,” “vice,” etc. spring to mind, and anyone who failed thereby become associated by default. What’s important here is that the association is automatic and almost Pavlovian – even if you recognize when a failure is not your fault, it still doesn’t feel good. It doesn’t FEEL good to lose a simple game of Monopoly even though it has zero bearing on your life. In my opinion, the negative feeling of failure is often disproportionately greater than the actual loss experienced therein. Nobody wants to feel like they’re worthless or incompetent, so I can certainly sympathize with the strong tendency to avoid it.

Failure is often only devastating because you believe it to be – do not let the fear of failure bind you to inaction. Since I am of the late millennial generation, reaching adolescence with the increasing prevalence of smartphones and social media, I’ve seen in person the grotesque motions of millennial courting rituals. I call it a ritual because of how ridiculous it is and how careful one must be to perform it. While the methods are numerous, there’s one unifying rule: don’t get rejected. Strange, isn’t the goal of courtship to express your romantic interest in another person in a way as to improve the odds that he/she will reciprocate?

Instead of asking a girl to go on a date, a guy might suggest “hanging out” over the weekend. This establishes plausible deniability of romantic interest – after all, he never explicitly asked her out. If she declines his offer multiple times as her way of indicating disinterest, he never “technically” got rejected and thus “technically” didn’t fail. The problem is, he ultimately exchanged immediate resolution for ambiguous, prolonged failure, with the emotional strain of uncertainty to boot.

What’s even more common is that a guy might never even find the courage to ask her to “hang out” at all but instead finding himself constantly mulling over the little things she does to determine if she likes him back. The key here is to show as little romantic interest as possible but also entice her to show enough romantic interest in him as to prompt him to finally act. This, too, is shallow attempt at preserving the ego by avoiding rejection/failure – if he never asked her out, he never failed. However, the girl might very well be going through the same mental gymnastics – a catch 22, indeed!

My first point is simple; emotions often blow failure out of proportion, resulting in taking a convoluted solution that’s worse than the problem to begin with. In the above example, instead of not knowing whether his feelings are mutual at this moment, he opted to not know for months, if not more, all the while wasting time and energy agonizing over not knowing.

The vast majority of the time, the worst-case scenario in a modern developed nation is trivial compared to any time in history. The worst possible outcome for an unproductive day at the office might be getting scolded by your boss, whereas the worst possible outcome for an unproductive day as a hunter gatherer is your newborn starving to death. If you fall and scrape your knee today, nothing happens; if you did that in the middle ages, you might die from an infection. Another great example would be modern US bankruptcy laws, which I believe incentivizes innovation and risk-taking, whereas debtor’s prison stifles them. Human emotions are wired to encourage risk aversion in a primitive world precisely because the stakes were so high, but these same emotions are no longer an appropriate yardstick for assessing risk/reward in the modern world. Unless you’re going all-in on TSLA put options or trying wingsuiting, failure is rarely ever as big of a deal as the preceding dread/anxiety suggests.

Sometimes, it is wiser to call it quits and cut your losses. I believe this is a natural caveat to the topic above – there are occasions when the optimal decision is to be the quitter and recognize your loss. The vast majority of these instances involve money, since it’s just so easy to lose, be it at the poker table or on the stock market. While the fear of failure could bind a person to inaction, it can also bind someone to a sinking ship. In the latter, quitting implies a recognition of failure and wasted resources, whereas continuing even the most moribund project implies a possibility of success. It is paramount to understand that contrary what your sports coach may tell you, quitting does not mean losing.

One of the best examples where quitting makes sense is in investments, where the saying “don’t throw good money after bad” applies so beautifully. Suppose you did weeks of thorough due diligence on company ABC and decided to plow a third of your savings into the stock, convinced of the company’s prospects. A year later, you find that the stock underperformed the market by 30% (suppose the underperformance is justified). How should you react? Let us examine the trains of thought by the quitter and by the loser.

  • The quitter reexamines his initial assessment of ABC and compares it to the actual results of the company and comes to the conclusion that his original thesis has been invalidated, i.e. he realizes that he was wrong. The quitter recognizes that it is only human to err and tries to learn from his mistakes (further discussed in the next section). He exits his position at a sizable loss.
  • The loser also looks back at his thesis, but instead of admitting he was wrong, his mind rationalizes away the counterevidence and chooses to believe that the market is still wrong. He is so averse to failure that he doubles down his position in a refusal to recognize the loss. Ultimately, he loses even more money in the classic investing mistake of throwing good money after bad.

At the end of the day, there’s no way of determining whether or not it is time to exit a losing position without taking an honest assessment of the situation. The key here is to exercise humility and to acknowledge your own fallibility beforehand. Remember that the time and resources you’ve already expended on a dying cause is irrelevant in deciding the right course of action going forward – you can never get back what you spent. Would you rather be the quitter who lost $10K or the loser who lost it all?

Learn from failure. It would be unbecoming to discuss failure without addressing how to profit from it. Oftentimes, after someone has failed, he tries to forget the problem as quickly as possible to avoid dwelling on the negative emotions. While there’s certainly merit to not dwell on a past failure, it would be wasteful to not learn anything.

Analyzing past failure should always start with introspection – (1) “where did I go wrong?” But that’s not to say the analysis should stop there, since that would just be punishing yourself emotionally with no gain. The first question should always be followed by (2) “what can I learn from it?” and (3) “how can I do better next time?” Suppose you were working on a school group project that didn’t go so well.

  • Without asking (1), you might draw the conclusion that the core problem was entirely out of your control, that it was all your groupmates’ fault, for example. Thus, your answer to (2) would be that your groupmates are terrible at teamwork, and thus (3) you shouldn’t work with them again. While there are certainly instances where things were truly not your fault, that doesn’t mean you can’t learn from the experience.
  • Without asking (2), you might be able to do better in the next school project, but you might not be able to generalize your findings for other applications, e.g. you might have a hard time translating your learnings in another context, like a collaborative project in the workplace.
  • Without asking (3), you might decide that you never want to work on a group project again and that you’re better off doing all the work yourself. Let not the initial failure alone justify dismissing something as a lost cause.

Failure is often impossible to avoid. You can do everything right and still fail. I won’t go into the debate between predestination and free will here, but from the perspective of a person with agency, the resolution of a given event with any degree of uncertainty is determined by probability. Ultimately, no one can ever have perfect information, so a person must be ready to acknowledge and accept that uncertainty. It should go without saying that even the best plan can go wrong, so as a caveat to learning from failure is that not every failure is attributable to a mistake or failing of character.

Perhaps you weren’t hired for a position that you interviewed flawlessly and prepared tirelessly for, simply because the company hired the chairman’s son instead. Perhaps you bought some airline stocks just before the coronavirus pandemic began in China. Or perhaps your carefully constructed vacation plan was derailed due to you getting food poisoning. None of that should deter you from continuing to improve and persevere and nor should you seriously change your approach purely on account of those failures.

The simplest example would be as follows: suppose you’re a middle-class office worker coming home from work. You meet an idiot with more money than brains offering you a gamble on a fair coin flip (you flip an ordinary quarter out of your wallet) where you stand to either lose $100 or triple it. You have a very good chance of losing, exactly 50%; however, you wouldn’t change your strategy for losing flips, since the correct play is to keep betting indefinitely. If you’ve only got $300 in your pocket, there’s a decent chance (exactly 12.5%) you’ll be coming home with an empty wallet. Nonetheless, despite your failure today, you’ll be back tomorrow looking for the same guy but now with $2,000 in your wallet.

Be honest about failure. It may seem like all I’ve written in the last few sections are a bunch of pointlessly contradicting generalizations: that sometimes failure can be much milder than you feel while other times it can be more devastating than you perceive; and that sometimes failure is your fault and other times it’s nobody’s fault. “Just what the hell is your point?” you might wonder, “none of these recommendations apply universally.” That is true. Ultimately, it is up to the individual to examine and interpret his own unique circumstance and to react accordingly.

Just how probable is the risk of loss and how devastating would failure really be? Should the situation be handled differently next time, under identical circumstances? Those two questions must be answered as honestly as possible for the best results. Meanwhile, the ego and emotional bias will attempt to steer the mind towards illogical conclusions and thus must be suppressed to arrive at a truly impartial judgment. Everyone experiences failure in one way or another, but the way failure is handled separates the mediocre from the truly remarkable.

In part 2, I will be examining why the presence of failure is so critical for improvement and why the pathological failure on both the part of the individual and society can be disastrous in the long-run.