Seth Godin wears many hats: serial entrepreneur, prolific author, beloved blogger and inspirational speaker.

He’s also a master at failure, mostly because he’s done it so many times. “I think it’s fair to say that I have failed more than most people,” Godin said today from his onstage perch at New York City’s Advertising Week. “And I’m super proud of that. Part of the rules of this game is, the person who fails the most wins.”

While liberating, this presentation of failure as a trophy isn’t new. Silicon Valley has long fetishized failure, to the point where “fail fast” has become an informal industry mantra; it’s not uncommon for business leaders and entrepreneurs to publicly present their failures like so many badges.

But as Godin goes on to clarify, failure is a skill. You can do it successfully, or you can fail at failure. “If you fail too big, you don’t get to fail anymore. If you never fail, then you haven’t done anything,” he said. The key is to find and consistently hit the sweet spot between those two poles. “If you’re failing consistently in a way where you get to keep playing, that’s pretty cool.”

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On one hand, Godin encouraged the 200-plus audience to pursue their “art,” no matter the lack of corresponding monetary gain or critical praise:

You have to get to the point where you say, this is what I’m going to make. And if [the audience] doesn’t get it, that’s ok…sooner or later they may get it. In Van Gogh’s case, they didn’t get it until he was dead. But that’s part of the deal.

At the same time, Godin gave a big nod to practicality. While the ability to risk failure is the essential in the pursuit of greatness, it doesn’t hurt to stack the deck in your favor and be strategic about your approach. If you feel your true artistic calling is to make toothpick sculptures, maybe take the process out of the woods and onto Kickstarter, where far-out projects often find an audience. Does it mean it’s going to gain traction? Of course not. But at the very least you’ve put yourself in a position where it’s a possibility.

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This balance – between failing too softly and failing too hard – is nicely encapsulated by Godin’s description of skate skiing, a sport he only recently discovered “The entire sport is, the person who leans forward the most wins,” he said. During his first lesson, he asked the instructor “what happens if you lean forward too much?”

To which the instructor, not unsurprisingly, replied: “You land on your face.”

For Godin, that tension – leaning forward as far as possible without landing face first in the ice – is skate skiing’s main draw. “It’s what makes people get hooked on skate skiing,” he said. “It’s the feeling I look for in every project I decide to do.”

In other words, don’t hold yourself back. But don’t aim to fall on your face, either. Instead, search for that magical spot where you push against your own limitations in pursuit of real victory.

In skate skiing and in life “you feel this moment where there might not be a net, where it might not work,” said Godin. And then you continue on anyway.

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