What is the single most underrated trait a person can have?

Which option do you prefer?

  1. I flip a coin. Heads, I give you $100,000, tails, you get nothing.
  2. I give you $1000.

Of course, like 90% of people, you’d take the $1,000, even though the expected value of the gamble is $50,000. In economics, the $49,000 difference is called risk premium. If you’re willing to take on risk, you stand to gain a large reward.

The reason most people aren’t is that they spend their entire lives chasing certainty.

In a 1951 book called The Wisdom of Insecurity, Alan Watts talks about the benefits of not craving certainty so much:

“I call it the ‘backwards law.’ When you try to stay on the surface of the water, you sink; but when you try to sink, you float. When you hold your breath, you lose it — which immediately calls to mind an ancient and much neglected saying, ‘Whosoever would save his soul shall lose it.’”

Today, the world is more uncertain than ever before, which makes the skill Watts talks about more valuable than it ever was.

That skill is called detachment.

It is the art of being okay when life sucks, because you’re removed from the expectation that it pans out a certain way.

Detachment enables you to do great things:

  • You can swing for home runs instead of second base, because you don’t need the $1,000.
  • You’re free to say “I don’t know,” because you don’t feel pressure to look smart.
  • You can always say how you feel, because you’re not worried about whether your feelings will offend others.
  • You focus on taking care of your own shortcomings, rather than pointing out others’, because you’re not so great just yet.
  • You don’t worry about being wrong, because it doesn’t matter if you’re right today or tomorrow. You can contradict yourself, but the world keeps turning.
  • You can just do your job and watch what happens, because it’s as good as any job on the way to figuring out your dream one.
  • You accept that life has trade-offs and make them, rather than constantly trying to bypass the fact itself.

Ironically, caring a little less helps you get more out of what you care so much about. Detachment allows higher demands and not settling for less. Ask not for certainty, ask for the best.

You only get one life. Swing for the fences.