It’s only a mistake if you make it twice

I used to encourage my teams and colleagues to ‘Celebrate Failures.’ Otherwise, we hide shared learnings from one another when we sweep mistakes under the rug in shame. The truth is, we all know this, we all fail from time to time. What’s important is learning and adapting. My idea behind celebrating failures was to remove the stigma around failing, while finding comfort in the vulnerability required to talk openly about it.

A colleague at Automattic recently discussed the idea in an internal post that people can become too comfortable with failing. Upon reflection, this has made me rethink the message of celebrating failures. The truth is, he’s not wrong. Self-help culture and philosophies seem to have shifted failures into medals of honor. As if failing is an automatic mark of experience and wisdom.

Failing fast (a.k.a., fail often or fail cheap) has it’s own wikipedia page. And of course there is more underlying nuance than simply aiming to fail. The idea is that you’re going to fail, so do it quickly and cheap. Yet, we cannot forget that today, nuance is often left in unread comments under a six-second video clip. So it’s important for us to be meticulous in the wording of our advice.

I read this quote in the book The Art of Fiction by John Gardner.

I never write exercises, but sometimes I write poems which fail and then I call them exercises.

– Robert Frost

Frost describes, perfectly and in one sentence, the way we should think about failures.

• “I never write exercises” – Meaning he’s aiming for success, for something worthy of the paper it’d be printed on.
• “but sometimes I write poems which fail” – I’m not infallible.
• “and then I call them exercises.” – I failed, it’s practice, I will learn from this exercise.

What better way to describe how to fail. I aim for success, sometimes I miss the mark, I use it to get better, I move on.

Going forward, I’m going to shift my thinking and rely more on the edict: It’s only a mistake if you make it twice. Reducing the use of the word failure which has become far too common, while encouraging us to find a way to learn from the experience.