Failing Your Way to Beating Everything

Many people who write in to this blog are struggling with overcoming some obstacle in their learning. From a lack of motivation to getting stuck on a plateau, it might be tempting to think that you’re failing to learn. However, there are two types of failure: one bad, and one good. I’ll show you why the good type of failure is actually necessary to learn.

It’s become something of a platitude that “failing is just a step towards success.” It’s even parodied in the popular HBO TV show Silicon Valley, where the Google-esque executive comically brushes aside failure as a good thing.


Jokes aside, self-help books are packed with pithy quotations about failure. There’s a grain of truth in the midst of all the self-congratulatory advice: failure is the only way to learn.

Edison: The Great Failure?

You’ve probably seen this quotation, or one like it:


It’s certainly a nice to know that even Edison “failed” so much when he famously invented the (commercial) lightbulb… but most advice hand-waves its way from Edison to “failure is good.” What some miss is that Edison did not fail randomly.

The difference between a successful failure and a wasted effort is experimentation. When a failure validates or rejects an idea, it leads to growth. Every time a hypothesis is tested, something is learned.

In other words, Edison did not simply try hundreds of random attempts at the lightbulb until one worked. That would have been masochistic and a waste of time. Nor am I suggesting that failing college classes is somehow a good thing. Instead, what is important is to learn and iterate after each failure, studying the failures to try to figure out which approaches might work.

Destroying Yourself

No pain, no gain.

This is yet another one of those overused sayings, but again, there’s truth at the core. If you’ve ever played a sport or competed as an athlete, you already know this. In order for muscles to grow, you must tear them. The actual destruction of the muscle is what tells the body to rebuild it (stronger, this time).

The body only ever grows in order to overcome some challenge. If everything were going smoothly, there would be no need to adapt. The heart of any self-improvement is creating conditions just stressful enough that rest will rebuild you to be better.

Putting Loops to Work

There is one very concrete way that failure is used every day in learning: through deliberate practice in the form of a core loop. One of the interesting similarities between learning theory, habit formation, and video game design is that they all use the language of a “loop.” Charles Duhigg drew a picture of his version of the loop in his book on habit formation:


I explained how core loops work in video games during a 4-part series of classes I taught on the topic of game design:

My point is this: every bit of improvement has always come at the expense of some difficulty. If you can put a name to that difficulty (“my legs hurt from running”) it can help you to beat it. Once something is identified it becomes real, and once it’s real it can be beaten.

This is closely related to the psychological concept of growth mindsets. In short, studies have shown that a focus on improvement trumps a belief in innate talent. So when you fail, reframe the failure in terms of a challenge… then approach the task of beating that challenge, next time. People who use this approach tend to succeed more, in the long run.

Exhaustion, Dilbert and Other Inspiration

The objection I most often hear to this philosophy of constant challenges is that it sounds exhausting. I can’t disagree, but I think it’s also more fun. After all, it’s the same stuff video games are built on. I’m not saying we should all pretend that life is a video game, but why not steal a little something from the psychology of how they work? You don’t need any special apps to change your own internal approach. Your “personal frame,” if you will. All you have to do is train yourself to think of things in terms of challenges.

About halfway through writing this post, I realized that it sounded similar to a book I had recently read. Scott Adams, the author of the Dilbert comics, wrote a book called How to Fail at Almost Everything and Still Win Big. It’s much funnier and his own success far surpasses mine, but I found in him a familiar approach to the world. One quotation stood out:

I can’t see the future, so I have the option of imagining it in whatever way gives me the greatest utility. I choose to imagine that the book will do well because that illusion is highly motivating. It increases my energy.

It was nice to hear that I’m not the only one who uses mental tricks like these. Writing a post like this, I feel like I’m walking a tightrope. There’s so much hyperbole going on in the self-improvement realm. Which is why the Silicon Valley TV show clip at the beginning of this episode nails it so perfectly. On the other hand, there’s some important power to be gained by using failure as a tool. Another one of the books I recommend is on this topic, called the Up Side of Down: why Failing Well is Key to Success. Here’s how author Megan McArdle phrased a similar insight:

the people who dislike challenges think that talent is a fixed thing that you’re either born with or not. The people who relish them think that it’s something you can nourish by doing stuff you’re not good at.

So the next time you’re thinking about failure, put it into the context of a challenge and ask yourself if it’s a failure that led to growth. If it did, then it was not a waste of time.


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