Learn from failure

My tai chi teachers taught me how to stand over the course of many years. There were many stances, each one intended to develop different internal forces. I emulated my teachers' stances and followed their directions as best I could. Then the other students would test me with pokes, prods, and shoves.

My stances were shallow imitations of the my teachers'. For years I stumbled back when pressed, but I persisted in my practice until, in fits and starts, I found my own way forward. Eventually there were no weaknesses left. I had grown deep, immovable roots.

There were three components to this training, generally speaking. First was my attempt to emulate my teachers and translate their experience into my own. The second component was the constant testing and failing that eventually, over time, lead me forward. This component was the most important.

The third component was when my teachers directed me to test my fellow students. By probing their weaknesses, I had many "a-ha" moments to help illuminate my own path. This component—other people's failure—is a part of learning often overlooked.

The happy path

It is tempting to try and emulate others' path to success. This type of modeling is an important step in learning, but there are real limits to how far it will take you. Almost all valuable insight comes from a deeply personal knowledge of your individual weaknesses and strengths1, not intimate knowledge of some other person's success.

There are a million stories in the wild about the millionaire next door. Households who found success through a rental empire, or by finding ways to cut their housing costs to the bone. People who managed to hack a path to victory from the stock market, or had a simple business idea that took off like wildfire. Plumbers and electricians who worked steadily, lived within their means, and consistently put money into savings.

Studying this kind of success can be dangerous. It is easy to find story after story of the happy path—stories about smart, talented, hard-working people. These stories tend to obscure the tattered outcomes of everyone else who walked the same path but was a little less lucky. People who were also smart, talented, and hard-working, but who did not quite make it to their happy ending.

Looking only at those who succeeded, and attempting to model yourself after them, is the self-improvement version of buying high and selling low. It sets you up for a losing game. It is known as survivorship bias, and it is insidious.

The truth is there are as many ways to win as there are games to play2. Your game will never be exactly the same as someone else's.

I know landlords who made it work, and I also know more than a handful of people who bought into the same markets but lost money because their numbers were wrong. Or because they purchased the wrong house at the wrong time. Or because they hit a string of tenants who cost them more money than they could afford. Or because they just did not have the knowledge, skills, or bankroll to make it work.

I know stock-pickers whose valid, true, and remarkable insights lead them straight to the poorhouse. Travel hackers who wound up stranded in Florence for a week because their brilliant plan fell apart at the last minute. Hustlers who got out-hustled. DIY-ers who paid twice: once to do it themselves, and once for someone else to do it right.

Always remember to study the losers.

All happy families are alike; each unhappy family is unhappy in its own way

Anna Karenina, Leo Tolstoy

Failure is a goldmine of knowledge

Here is some homework: find someone who blew it, big time, and is willing to talk for an hour. You will get more of an education from them than any college-level business course. If you are paying attention, you will come away from these sorts of conversations with an understanding of how contingent success can be, the toll of mental illness or drug use, and any number of other lessons you will never get from looking at the happy path.

By studying failure as well as success, you build a more complete picture of what it takes to succeed. It also gives you the knowledge you need to train yourself to be wary where you need to be wary, instead of focusing only on when and how to be eager.

Failure is a greater teacher than success.

Andrew Reeves is an entrepreneur, touring musician, and practitioner of eleven martial arts. He reached financial independence at age 28 and has dedicated his retirement to fighting crime and helping others.


  • 1

    This is true even if your weaknesses and strengths are common ones.

  • 2

    Which is to say, an infinite number.

When have you learned from someone else's failure? How often do you practice your stances? Have you ever focused so much on the happy path, you became blind to everything else?


steveark says

I respectfully disagree, even the most successful people have a history of dumb decisions and personal failures more than sufficient to provide "what not to do" lessons. Plus they show how to fight through failure and win. I don't really want to learn how to fight failure and lose. But it is an intriguing argument and both sides may be right.

October 17, 2017 at 10:55 am

Fair point! Everyone does dumb things, and everyone has their share of failures. I think we're almost on the same page, particularly since I'm not trying to label the people as successes or failures. It is individual projects/businesses/etc. that succeed or fail. Most successful people have blown it at least a time or two in their lives, in one area or another.

One aspect of what I'm putting forward is that if you could only have one conversation with Warren Buffet, you would probably get more out of hearing him talk about the times he lost gobs of money than you would from hearing him talk about how he became rich.

The survivorship bias article linked to in the post goes into more detail about the dangers of looking only at success. Definitely give it a read if you haven't already.

October 17, 2017 at 4:36 pm

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