Fail fast and often. You've probably heard this, right? It's a common saying these days. It taps into this idea that there are so many opportunities to succeed, you might as well take all the leaps you can get.  It'll be worth it in the end, all those failures will lead up to one big achievement, etc.

But is it hype? Is failing really that important? Should you believe it?

Yes. Absolutely, yes. Failure can teach you a tremendous amount.

Sometimes you have to take 10000 punches before anything good develops. Miracles don't happen. If they do, it's one in a million. You have to work, you have to put yourself out there. And with work comes disappointment. The more you work, the more instances you have for disappointment.

So yes, failure is necessary and will happen if you are truly taking the risks required to make it.

But the failure has to be quantified.

If you fail and can never get up from it again, that's not a good kind of failure. As an entrepreneur, all my failures along the way have been a lesson. I failed a test in fourth grade, and I see it as one of the greatest achievements of my life because it forced me to realize what I truly wanted to do with my life. No joke. I distinctly remember sitting in my small bedroom, crying and debating in my own head, trying to make sense of why I was having such an intense reaction to this test. And then it hit me. This was the thought that changed everything: "Screw school. I'm a businessman."

I'm even just now thinking back to when I attended my first baseball card trade show. I bought a table at 13 years old for $400 and nobody showed up. That was a certainly a lesson. And I just had to go through it.

Those micro-failures were very important for me. They were small but significant. But you need to put the failure in context of what could happen. A possible scenario is you could go completely out of business. Usually people go one of two ways when that happens: either they are finished and never get up again, or they start over and try harder. Which outcome sounds more like you?

This brings me to legacy over currency. It goes right along with quantifying the failure. You always have to be considering your legacy in the decisions you make. I've been saying it since 2008. What do you want to be remembered for? What is going to be your life achievement? Figure out what that is and then make sure every decision you make leads up to it. If failure becomes a part of that, so be it. But never forget the end game. Even if something seems like it's going to be a sweet deal, weigh it against what you ultimately want to be doing.

So yes, believe the hype: the more you fail, the less you're afraid of it. That's a good thing. But not all failures are equal. Some could totally destroy you. Quantify. Consider the outcomes, and remember your legacy.

--This story first appeared on Medium.

Published on: Apr 22, 2015