If you’re not making mistakes, you’re not taking enough risk

A college freshman recently asked me for some career advice. We chatted for almost an hour, yet I said almost nothing useful.

The most useful advice is the most obvious (eg, work hard! treat people well!) and all other “advice” is often just a case of shooting an arrow then drawing the bullseye.

But at the end of our chat, there was a little nugget of something useful that appeared by accident. She asked me:

“What’s the most important piece of advice that you’d give me?”

I thought about it for a few seconds and made up replied with the following:

“Make mistakes. If you don’t make mistakes, you’re not taking enough risk.”

I think I take risks. Most people do. Especially entrepreneurs. But how do you know you really do?

A useful definition I once read is “Risk means more things can happen than will happen.”

Most of the things that “can happen” are things you don’t want to happen. Mistakes.

How do you know it’s a mistake?

Well, when it happens, you feel bad – embarrassed, disappointed, angry, sad. Any of the million emotions that shrink the ego instead of enlarging it. You want to hit rewind, or disappear from view.

In his Oscars acceptance speech, Ben Affleck said, “It doesn’t matter how you get knocked down in life; that’s going to happen. All that matters is you’ve got to get up.”

Feeling bad is the emotional equivalent of getting knocked down. It’s a straight jab to our ego. When you get that feeling, you should tell yourself: You’ve made a mistake. You’ve taken a risk.

Then you should get up and get going.

Because when you take a risk and it works out, it is sweet. It is the opposite of feeling bad, times 10. And that process, of taking risks and making mistakes and reaping rewards, is what enables human beings throughout history to build cities, create billion-dollar companies, discover atoms and planets.

But if you’re not making mistakes, if you’re not doing things that make you feel bad, if you’re not absorbing body blows to the ego, if everyday there isn’t a moment where your face flushes hot and you feel your gut literally sinking, then you’re probably not taking real risks.

Just some food for thought. Here’s more:

  • Chris Dixon puts a different — and clearer — spin on this
  • Scott Adams, the creator of Dilbert, has a wonderful and relevant story

Click here to read about the daily habits that I track and why.