Quitting Is For Winners


“Complete a project by dropping it altogether.”

I saw this Arianna Huffington quote on my friend’s Instagram feed and it resonated like a tuning fork.

Letting go is hard for us to do because we were raised on a puree of grit.

“Don’t give up.” “No pain. No gain.” “Never quit.”

Fair enough. But there’s no glory in figuring out how to gain grip on a spinning tire if fresh traction is only going to send you careening off a cliff.

So how DO you know when you should quit and when you should stick with your current project/business?

We’ve all tried to solve this conundrum as the festering demon in our head burrows its plump ass to the crossroads of “necessary” and “cowardly” and steals the street signs.

In his book, Uncertainty, Jonathan Fields had a great four-question exercise to deal with the impasse of “should you or shouldn’t you?”

I’ve thrown in some random examples behind Jonathan’s questions:

Is this project something your body must do, regardless of whether you ever make enough money to live truly comfortably doing it?

  • If working on your screenplay is part of your DNA and part of what defines you as a person and you couldn’t imagine your life without it even if you never sell it, then maybe it’s something you stick with.

Are you more interested in the medium you’re working in and your proposed solution or are you only interested in serving a particular market?

  • Do you really need to create a social network for travelers to better connect the wandering tribe or could you possibly feel successful being a tour operator, being a travel writer, working for a travel magazine or holding an international sales job?

If your ultimate goal with this project seems like it is something that actually might be possible, would you still want it to happen?

  • You’ve put in so much work to get where you’ve gotten to. You actually might be able to open this pop-up shop after all. Is this still something you really want? Are you ready for success? Are you ready for judgment? As time passes, so do motivations. Don’t just stick with something because you wanted to do it once. Make sure that the goal is still in line with your motivations.

Would the results and feedback you’ve learned so far force you to change your original goal so much so that while it still might lead you to success, the final output/career will no longer match the motivations that made you start on this journey in the first place?

  • Maybe you set out to open a restaurant but it’s not looking good. However, in your process you’ve become really good at raising money. You can now make a good living being a consultant for other people starting businesses in the restaurant world. Is that good enough to bring you joy or would you need your own restaurant?


I’m usually the first guy telling people that they need to finish more than they start but finishing what you start is also about abandoning what doesn’t work. 

And to be fair to yourself and your efforts, this abandonment should be after some conversations, checkpoints, and check-ins (like the questions above), not after a caffeine crash, a cocaine binge, or a case of  insomnia.

What will people ultimately say if you changed your mind, if you quit doing what you started because it just wasn’t the right thing to do?

Nothing. They’re dealing with their own demons. The only voice you’ll need to manage is the one in your head.

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