Failure for Dummies

One of the hallmarks of a quality learning environment is that it permits learners to fail. We might conclude that the primary reason is that without the possibility of failure, success is meaningless. As true as this is, there’s a whole lot more to failure and the part it plays in learning and life.

We tend to hate failing—even just making small mistakes—because we approach most situations with a self-evaluative mindset. In this way of thinking, when we fail or err, we’re WRONG, BAD, STUPID, and a LOSER. We’re perpetually ready to judge ourselves and don’t want a negative judgment. Put another way, we “play not to lose”.

According to Po Bronson and Ashley Merriman in Top Dog: The Science of Winning and Losing,

“Playing to win means focusing on success, whereas
playing not to lose focuses on preventing mistakes.”

We’re all familiar with the notion that somehow success is built on failure; there’s practically an entire genre of leadership books dedicated to the idea. But how does it actually work? How does failure become success? And more importantly, how do you intentionally go from playing not to lose to playing to win?

If the intention of playing not to lose is to minimize failure because failure is BAD within an evaluative mindset, then we might suspect that the goal of playing to win risks failure which can be GOOD within an assessment mindset.

It turns out that’s pretty much the case. According to, The big idea: why we need to learn to fail better, there are different kinds of failure. There are what I’ll call ‘stupid fails’ which is failing the same way as you have before or failure in areas where you truly should know better (such as a surgeon cutting off the wrong limb or causing an accident by driving drunk). Then there are what the article calls “intelligent failures”. These are novel failures in new areas. When you fail intelligently, you’ve minimized risks as much as possible, but then bite the proverbial bullet and take any remaining risks.

“Failing well is about increasing the frequency of intelligent failure
where the upside more than compensates for the downside.”

A perfect example, the article suggests, is a blind date. There are a lot of obvious things you can do to make sure you’re going to meet someone who probably isn’t a psychopath, but after doing those things, you do have to take a bit of a leap into the unknown.

I generally think of this as putting on my Crash Test Dummy sticker. When I’ve done what I can do make sure I’m not going to make a stupid fail, I metaphorically slap the sticker on the side of my head and give it a go. The whole point of a crash test dummy is to be present during vehicle failure in order to collect critical information (such as impact force/velocity). It’s the collecting of critical information AND WHAT IS DONE WITH IT that matters so much. The article refers to this as “research rather than failure”.

Put into context, playing to win is where we risk intelligent failure so we can gather information we can then use to improve our performance, which brings us closer to success.

Playing not to lose is a cycle of performing in a way that minimizes the chances of failure then judging your performance. Playing to win is more like a series of hops toward success where you risk performing (be a crash test dummy) then gather information and use the information to perform better.

We see the difference between the two approaches and how it is that intelligent failures (the process of failing well) brings us closer to winning or success. But what about how we go from the one mindset to the other?

According to the article, the shift occurs when you work to replace the fear of failing with being curious and willing to learn. It becomes an intentional process of feedback and improvement. And as Top Dog adds, “Growth happens when you play to win.”