About 5 years ago, embarking on a new project with a colleague, the challenges we faced seemed infinite and overwhelming. We doubted our direction and our drive. As we were struggling with whether or not to continue, a friend handed me Seth Godin’s book, The Dip: A Little Book That Teaches You When to Quit (and when to stick). I read the book, and had my answer. We just had to stick it through! Godin explained two kinds of hard: the hard that’s part and parcel of a worthy endeavor, and the hard of hitting your head against a brick wall over and over. It was inspiring, so I called up my colleague. “This is it!” I raved. “You have to read this book. It’s exactly what we need!” Sure, she said.

Three days later I got a call.

“I finished the book,” she said.

I heard the note in her voice, and my heart sank. Not yet willing to confront the truth, I hopefully asked, “Well, what do you think?”


“It’s just not right for me to push through.”

Over the course of my career, the one single question I have been asked the most is this:

How do I know when it’s time to leave? Do I stay or do I quit? Do I push harder, or am I being foolish in doing so? How do we know, in the words of Kenny Rogers, “when to hold ‘em and when to fold ‘em?”

Whether people are asking about a relationship, job, or project this is the single most vexing personal issue question I get asked. I recently saw this on Elizabeth Gilbert’s Facebook page, QUITTING vs. SURRENDERING. Someone asked her whether she should continue working on a frustrating project or quit. Was it time to work harder? Or time to let it go?

Insightfully, Gilbert says, IT DEPENDS. Good arguments, she said, can be found on both sides: sometimes you stick with something for too long and regret it. I can’t tell you how many people have said to me, I should have left/quit/stopped a long time ago. On the other hand, the same can be true for leaving too soon. Just as many people have said to me that they regret having left too soon. They missed an opportunity because they succumbed to their reactions, frustrations, or fear.

Gilbert thus reframes the question in terms of “quitting” vs. “surrendering.” Surrendering is good; quitting is bad. And for many people, that is a helpful distinction. My colleague surrendered. She didn’t quit. She surrendered to the fact that her heart wasn’t in it. She surrendered to the truth of her real interests and passions. And ultimately it was great –for her, for me to continue alone, and for our relationship. We now collaborate on a different project, one that is way more aligned with her passions as well as mine.

But back to the question: how do you know? Godin had his method for knowing, and Gilbert has hers. But I have mine, too. When people ask me, should I leave? Should I find a new job? Work somewhere else? Leave this relationship? Stop pushing to make this project happen? I counter with this question:

Have you changed yourself enough?

Most stick/quit discussions revolve around this one, central problem: the other person, project, job, institution isn’t what I want. It won’t change. It won’t respond as I need it to. It won’t be what I want it to be. It won’t move in the direction to where I want it to go.

So my question always is: have you moved? Have you changed? Have you increased or expanded yourself enough? In the terms of process-oriented psychology , a change method I am steeped in, have you crossed your edges enough?

So here is my algorithm, the questions I ask people to consider, when they are contemplating quitting:

  1. Who do you want to be?

Hard things change you. So, first of all, ask yourself, do you want to change in the direction being asked of you? Is it right for you to change? If not, then you will resist the changes being asked of you. Then things will be arduous, but without yielding positive results.

My colleague was savvy. She knew that the changes required of her to stick with the project weren’t right for her. She had other passions and other things to develop. For me, on the other hand, it was totally right.

  1. Have you changed enough?

If the changes required feel right to you, then ask yourself, have you done everything you can to meet the challenge? Have you changed enough? Whenever we hit an obstacle, when we encounter the same response from someone, whether in workplace relationship, romantic relationship, or friendship, we have to consider that their stubborn and chronic response is in response to our stubborn and chronic actions. As my mother always said, “It takes two to tango.”

We grow and develop through the effort and if we expect to not be stretched, not be challenged to change ourselves, then how do we expect the other to? Have you expanded your skills, abilities, attitudes, or sense of self sufficiently, to do what is required to succeed with this challenge?

Sometimes I get a hopeless response, “Yeah, but it won’t matter what I do,” the other person says, “they or it still won’t change.” And I counter, “How do you know? You haven’t given the other person a chance to respond to something new. If you can be different, so can they.”

  1. Have you done what you want the other to do?

Frequently we get so caught up pushing for change on the outside that we haven’t fully mastered the change on the inside. It’s important to ask ourselves, are we doing what we expect the other person to do? In other words, if you are asking yourself whether or not to leave a person or a group, have you sufficiently become the thing you want them to be? If you’re just pushing against the other, without pushing yourself to change in the same direction, then maybe you have more work to do before you quit.

But, if you’ve answered yes to all three questions, then maybe it is time to consider, where to next?

How do you decide when to hold ‘em and when to fold ‘em?