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As a comedian, I sometimes view the world with a cynical eye, asking: ‘What’s funny here? What’s so ridiculous it deserves to be made fun of?’ But this week, on a tiny island off the coast of Croatia, it is tough to be cynical. I’m here as host of a two-day marketing event, and I’m the ‘Mayor’ of the Island. And here I am, un-cynically inspired by a bunch of people psyched to be together for an afternoon Fun-Run. And yeah, it’s hard to see the phrases ‘Fun-Run’ and ‘Mayor of the Island,’ and not add them to the ‘what’s ridiculous’ list.

The island is amazing. It’s so cool that we took a speedboat to get here. (yellow alert: link is vaguely NSW) It reminds me of the island in Myst, but with fewer puzzles, no Linking Books and a lot more young (don’t-call-them-influencers) social media users running around and laughing and posting pics of themselves running around and laughing. And if you don’t know what Myst is you must be either not old, not a nerd or both.

But really, it’s the people who are inspiring. These runners don’t quit.

And that’s good, right? That’s the rule, isn’t it? Quitters never win and winners never quit. That’s certainly what we teach our kids: never quit! Even when your football* team is down 8-0, you hunker down and keep fighting til the last whistle blows.

But is that really good advice? In business we tell people to take risks, fail fast, and learn from the failure. Facebook’s motto was famously, ‘move fast and break things.’ (Or was it ‘move fast, break things and secretly sell user data’?) Companies and future American presidents know that declaring bankruptcy can be smarter than running a company that’s losing money. Even Kenny Rogers wisely noted you’ve got to know when to hold ’em and know when to fold ’em.

And sometimes when you’re working on a task that you just can’t crack, it’s best to stop, clear your head, and come back to it later with fresh eyes. You don’t just stare at the screen hoping for a miracle because ‘only losers quit.’ I guess that’s not quite quitting with a capital Q, because you come back to the problem later. But it is admitting that you just can’t solve it here and now.

And who wants to stay in a bad relationship because, dammit, we’re not quitters? Once your girlfriend tells you, ‘We’re not breaking up; we’re just seeing other people,’ it’s not time to hunker down. It’s time to freshen up… your Tinder profile.

So why do we ask kids to keep playing til the humiliation is complete? Why not set a 6-0 rout rule? At 6-0, we know how this thing ends; let’s agree that no one is having any fun, shake hands, and go home. Hell, we could do it adult sports too. Why should Thailand have to watch team USA beat them by a crushing 13-0 in the World Cup? We get it; Alex Morgan is awesome. But did we have to watch her score five times? That’s just mean. Like Kenny would say: know when to walk away.

We ought to teach children the same thing we need to remember as adults: Sometimes the answer is simply, we did our best, but we’re done here. Let’s try something else. Sure, on Apollo 13 failure was not an option. But when you’re iterating a new concept or project, you have to take a risk, make your up or down call, and move forward. And sometimes moving forward means moving away from this idea and trying another. When you’re banging your head against the wall, maybe it’s time to step away from the wall, and take a break. Walk your dog. Play with your kids. Take a speedboat to an island and go for a Fun-Run.

By the way, even on this island, these runners know when to stop. They challenge themselves to ‘run through the pain.’ But they don’t challenge themselves to ‘run through the pain of a myocardial infarction.’ That’s when you quit running and call an ambulance.

*I live in the Netherlands. So I mean the football you play with no hands. I don’t mean the football you play with body armor, a helmet and too much growth hormone.

Pep Rosenfeld

PepPep Rosenfeld

As Director of Creative Content, Pep does it all: He’s a high level event host & facilitator, writer, stand-up comedian, public speaker, coach, and developer of innovative corporate programs. A co-founder of Boom Chicago, Pep’s passion is using comedy to make hard-to-communicate messages land and stick, as featured In his 2012 TED talk, ‘Fight, Flight or Make Your Opponent Laugh.’ Pep hosts events like TEDx Amsterdam, The Next Web Conference, The Nordic Business Forum, and the Spin Awards to rave reviews, and he was nominated for an Emmy for his writing on America’s long-running television show, Saturday Night Live.