Quitting

How do you know when it’s time to quit?

We all know people all over the spectrum. Someone who’s been working on something forever that’s never going to work out. And someone who quits every project they start before giving it a fair chance. Then we have those friends who seem to have the magical instinct to know when to quit and when to stick with it until it takes off.

So how do you know when to quit? 3 months? A year? Is there some signal to look for?


Here’s something that’s been nagging the crap out of me. I can’t get an article published in Entrepreneur. I’ve tried. Three times. More than that actually since I’ve re-pitched articles working from the editor’s feedback.

The editor just doesn’t like my stuff. No amount of traction from previous work moves his opinion.

But I’d love to continue growing my audience and Entrepreneur seems like such a great fit.

Do I give up?


Most of us have a lot of goals inside our head.

For me I want that article in Entrepreneur. I want more subscribers on my YouTube channel. I want to grow Highrise. I want to be my own boss. I want to spend as much time as humanly possibly with my family.

All these goals are a jumble inside our own heads. But the goals aren’t all of equal importance. And that’s the first problem we have before deciding to quit something.

Angela Duckworth offers a framework to help sort through your goals, in her book Grit, that’s deceptively simple and incredibly useful.


It’s a bit like a ladder. On the bottom are the smaller goals of less importance. Bigger ones above them. One or more of the goals below often support the ones above.

The Entrepreneur article is probably way down here.


While ensuring more time with family is at the top.


Here’s the magic of the ladder. As you go up, the goals should be things that you consider harder and harder to quit.


I should make sure I spend every last drop of energy and willpower I have to ensure I have the ability to spend more time with my family.

And Highrise, is, of course, of insane importance to me. But I should consider it easier to quit than say maximizing time with family.

As you go down the ladder, you realize getting an article in Entrepreneur is one of things I should probably consider the easiest to give up.

And here’s more magic with the ladder. Not only are the lower things on the ladder easier to quit, they’re easier to replace.


There are tons of small goals to replace that damn article in Entrepreneur. I could change my focus to getting published in Inc. Or spend more time on YouTube videos.

The middle goals are harder and harder to replace but they’re still replaceable. There’s nothing to replace more time with my family.


So when you start asking about when it’s time to quit something, hopefully you’ve done this exercise and at least figured out that jumble of goals in your head. This thing you’re trying to quit, is it of low importance serving the needs of the actual higher goal? Is it then easy to replace to move focus to higher rungs in the ladder?

It’s not a magic formula for which projects to quit after trying hard for 6 months, etc.

But it sure is the right place to start.

P.S. You should follow me on YouTube: youtube.com/nathankontny where I share more about how we run our business, do product design, market ourselves, and just get through life. And if you need a zero-learning-curve system to track leads and manage follow-ups, try Highrise.


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