Jake LaCaze

Managing expectations with a failure-first mindset

All too often, we contemplate how we want to succeed.

What would you do if you knew you were destined to succeed?

Go do that.

So the wisdom goes.

But sometimes it pays to look at the other end of the spectrum. What if your venture is doomed to fail? For this thought exercise, assume there’s no way to salvage things. You’re going to fail, no matter what. The question is how you’re going to fail. What will that failure look like?

What do you need to do to ensure you can be proud of your failure? When do you need to speak up? When can you take control?

Even if you have control of only 1% of the situation, that 1% is everything. So own it. And do so in a way that lets you hold your head up high when the whole operation blows up around you.

This line of thinking is more useful than daydreaming about immense success, leading to great disappointment when the success doesn’t materialize. A pessimist might say my proposal dooms people to failure, because they’re expecting things to go badly. But I disagree. The point of my thought experiment is to accept the possibility of failure so that you can focus on the process and conduct yourself in a way that makes you proud.

Failure is far more common than we like to admit. The vast majority of new businesses fail within only a few short years. Those who succeed do so because they’ve stopped doing the things they were failing at. The beautiful thing about the failure-first mindset is that it ensures you’ll be pleasantly surprised if you’re wrong. Compare that to the feelings associated with being wrong when you lean into a success-first mindset.

As I recently heard paraphrased on an episode of The Tim Ferris Show featuring Morgan Housel1:

Happiness equals reality minus expectations.

Some people claim failure is never an option. But I argue failure is often the default option. Perfectionism is a fool’s errand. Working to become comfortable with failure is a far better use of time.

So, now I ask you:

What would you do if you knew you were destined to fail?

Go do that.

Jake LaCaze is highly successful at failing.

  1. Morgan Housel on The Tim Ferris Show ↩︎