Try Failing On Purpose (It May Even Be Fun)


Many of us have a deep fear of failure.

We imagine it to be the worst thing possible in our lives: What happens if that person at the bar rejects me? What happens if my band does terrible during our first show? What happens if people say my new blog sucks?

We’re so afraid of what people may think about us that we end up never doing what we really want to do, because we’re scared that we are going to suck at it and embarrass ourselves in front of everyone.

If we want to reverse this pattern, we need to learn that not only is failure a necessary first step to success, it can also be kind of fun. That’s right, let me repeat that: failure isn’t so bad, it can actually be kind of fun.



Thomas Watson, the former president of IBM, once said “If you want to succeed, double your failure rate.”

This quote has always stuck with me. It sounds like we should actively TRY to fail more often, which seems counter-intuitive. However, the more I thought about it, the more it began to make sense.

Trying to fail on purpose teaches us a lot of valuable lessons. Just some of these things include:

  • Failure lets you know that you are going out of your comfort zone and trying new things.
  • Failure teaches you what your current limitations are and what you need to work on to improve yourself.
  • Failure shows you that failure isn’t that bad. The more you embrace failure, the more you become desensitized to it.

Most of the failure that we fear in our lives is pretty inconsequential. The world isn’t going to end, you’re just going to maybe feel a little temporary pain and embarrassment.

However, by the end of the day, you’re probably going to feel better for putting yourself out there. The pain of trying and failing is a much smaller pain than the pain of never trying at all.

My recommendation to you: try putting yourself in more situations where you know you’re going to fail.

Don’t put yourself in any situation that is too serious or life-threatening, but put yourself in an extreme situation where the likelihood of you succeeding is small.

For example, I was recently at the batting cages. I’m not that good, so I usually go where the pitches are 50-60mph. However, I purposely tried out one of the harder ones knowing that I was going to do terribly. And I was right.

My brother and I laughed about how poorly we did, but it was fun. And interestingly, when we went back to our normal pitching speed, it actually was much easier to hit the balls.

Exposing yourself to more difficult situations heightens your threshold for success, so that when you go back to other less difficult situations, it makes them appear much more easier and do-able.

So don’t be afraid of failure in your life. Do the opposite: actively embrace it and find situations where you know there’s a good chance you’ll fail. That’s one of the best ways to test your limits and keep you on a constant path of self-improvement.


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