You Should Have More Spectacular Failures

Most advice is calibration. Eat less (because you’re inclined to overeat). Study more (because you’ll probably wait too long and cram right before the exam). Procrastinate less (because you’ll probably spend days stressing about trying to do the thing that if you just did it now, it wouldn’t be all that bad).

I try to think about how I’m biased in ways that leads me away from the ideal point between extremes. One way that I’m biased is with failure. I avoid failure too much, and I think you do too.

Failing too little might seem like an odd worry, but I like to worry about odd things. Because only having successes probably means you’re being insufficiently bold in your plans and ideas. If everything you do is a success, then you’re playing it too safe.

“Ah! But I fail all the time,” you say. “It must be nice to succeed constantly so that worrying about failing too little is your biggest worry,” you add, with more than a dollop of sarcasm.

I fail too. But what I’ve noticed is that usually when I fail, I’m rarely trying my hardest. Instead, what happens, is that I think I’m going to fail and I start holding back. I divest resources, I procrastinate, I don’t really try. That way, when the failure inevitably comes, I can hold in my mind the idea that I didn’t really care in the first place.

Fragile Egos and Spectacular Failure

All of this only serves the purpose of preventing me from bruising my ego. By withdrawing resources early (sometimes before I’ve even begun), I can protect myself from failure in advance.

So, no, my suggestion isn’t to simply fail more. Many people intuitively feel like they do enough of that already.

Instead, my suggestion is that you should fail more spectacularly. Fail when you really did try your hardest and there was no way for you to have done better. Fail with the same zest and enthusiasm as when you succeed.

I’m also not arguing that you need to burn yourself out more often either. However, if you’re like me, you’ve probably noticed a distinct difference in your investment of effort when you’re about to succeed and when you’re about to fail. In the former, you’re not always burning yourself out, but you are actively participating. In the latter, you might spend days just to begrudgingly make any progress at all.

Make Failing Spectacularly Your Mission

Honestly, sometimes aiming for success just leads to procrastination. When your goal is to do well, the fear of not being able to reach it can undermine your performance. You fear failure so much that its possibility causes immediate aversion to doing anything. Better to fail out of laziness and protect your ego.

However, sometimes you can overcome this by flipping your mission. If, instead of anxiously hoping for success, you expect to fail completely while trying your best, you become more open to putting effort in. You become interested in the process instead of the outcome.

Bootstrapping Confidence

I’m not a big fan of the belief-equals-reality drivel behind ideas like The Secret. I’m a pragmatist and I think that there’s an important sense that what happens to you in life comes from a materialist account of cause and effect. You lose weight because you eat fewer calories and exercise, not because you hallucinated yourself twenty pounds lighter.

However, I do think that confidence plays an incredibly important role both in how you select your goals to begin with and how you carry them out once you’ve started. If you have more confidence, you consider a broader range of ambitions. Once you start, you work more earnestly and push through obstacles instead of viewing them as signs that your endeavor is doomed to failure.

But all of this raises a question—if you don’t have confidence, how do you get it? You can’t simply will yourself to have more confidence, so even if being more confident could allow you to set more ambitious targets and achieve them, what good does that advice bring?

My feeling is that you bootstrap confidence by aiming for failure. When you enthusiastically embark on a project you sincerely doubt you can achieve, then its success (or even failing less than expected) adjusts your confidence upward. Lowered expectations of success allow you to bootstrap confidence until you hit the limits of your abilities as defined by objective circumstances.

Real or Imagined Limits?

I think, within each of us, we have a scope of what we’re capable of. This is defined in one of two ways:

1. What we have personally experienced. If we have personally learned a second language, we believe we can learn a third one. If you’ve successfully gotten in shape before, you believe you can do it again.
2. What we see from the experience of others. If you see other people like you typically achieving a result, you’re more likely to believe you can do the same (although this is much weaker than having done it yourself). As a result, most people get driver’s licenses without issue because of the strong societal presumption that most everybody should be able to do so.

The problem with these definitions of our limits is that they’re incredibly narrow. As a human being you’ve probably lived only a few decades, and almost certainly no more than ten. As a result, your personal experience compared with potential experience is a drop in the ocean. It’s simply not possible to personally try each and every thing that you would eventually be able to do with effort.

When it comes to the experience of other people, since most people are also judging their personal capabilities based on the experiences of others, this leads to a conformity bias. Without a strong exogenous pressure to succeed in a particular pursuit, most people won’t engage in it, and it will lie outside the collective limits of most people, and thus outside of one’s expectations for success.

These imagined limits are probably much more restrictive than our true limits, as defined by our innate talent, motivation and discipline. This is especially true when considering unconventional goals that we don’t have a strong external pressure to succeed at.

As a result, I believe that with most people, the aversion to failure, combined with the limited personal experience and limited societal expectations for success, mean that we’re too conservative with our expectations for ourselves. Occasionally there are people with unnaturally excess confidence (often without excess ability) and those people tend to accomplish more by virtue of this gap between our real and imagined limits.

Eventually real limits will be reached. But I’d much rather fail at the margins of my ultimate potential than some imagined capacity, designed to protect my ego from failing when I was really trying my best.

Those who aim for spectacular failure will fail more. But they’ll also succeed more, and perhaps more than they originally imagined.