Julie Diamond, Ph.D., author, executive coach and international leadership consultant

As the year comes to a close, I take a bit of time to reflect on the year that was, and the year to come. It’s one of my favorite parts of the year, because it’s the time when we get to think long and hard about things (long dark nights help)  about things we’re grateful for, about our choices and direction, and of course, things we want to change in the coming year.

While some changes are hard, they are also obvious: we definitely want to quit smoking, or eat healthier food, or start exercising more. We want to learn a new skill, change jobs, or show up more boldly at work or in relationships.

But some change is less obvious. And this is confusing. One of the least obvious and thus most difficult changes involve leaving. How do we know when to quit something or someone and when to stick it out?

I faced that challenge, about five years ago, when a friend and I embarked on a new project.

The obstacles we faced seemed infinite and overwhelming. We had drive, but doubted our direction.

As we struggled with whether or not to continue, I was telling my tale of woe to a friend who recommended I read Seth Godin’s book, The Dip: A Little Book That Teaches You When to Quit (and when to stick).

I gobbled up the book in an hour (Seth Godin’s books are like that), and knew my answer. It was so obvious! We just had to stick it through. It was tough, but that was part of the journey.

As Godin explained, there are two kinds of hard: the hard that’s part and parcel of a worthy endeavor, and the hard of futility, of hitting your head against a brick wall over and over. It gave me such clarity, 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.

A day 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.”

That was tough news to take.

It’s amazing to me that over the course of my career helping people, the one single question I have been asked the most is this:

How do I know when it’s time to leave?

Whether people are talking about a job, a relationship, a creative project, or a political cause, the question that vexes people the most is: Do I stay or should 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?”

A few years ago, Elizabeth Gilbert shared a post on her Facebook page called QUITTING vs. SURRENDERING. Someone had asked her whether to continue working on a frustrating project or quit. Was it time to work harder? Or time to let it go?

Gilbert says, IT DEPENDS. Good arguments can be found on both sides.

Sometimes you stick around too long and regret it. Nothing changes or gets better and the time and energy you have invested seems wasted.

But on the other hand, leaving too soon can mean missing a golden opportunity because you succumb to your reactions, frustrations, or fear and walk away before the payoff.

Gilbert thus reframes the question in terms of “quitting” vs. “surrendering.”

Surrendering, she says, is good; quitting not so much. And for many people, that is a helpful distinction.

Back to my story. What I discovered is that my colleague didn’t quit. She surrendered. She surrendered to the truth that her heart wasn’t in it. She surrendered in the direction of her real interests and passions.

And ultimately it worked out – for her, for me, and for our relationship. Although our original endeavor didn’t pan out, we began to collaborate on a different project, one that is more aligned with her passions as well as mine, and one that turned out to be very successful.

But back to the question: how do you  when to stick it our or when to quit?

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 always counter with two questions:

Have You Changed Enough?

Have you done everything you can to meet the challenge?
Whenever we hit an obstacle and seem to encounter the same  obstacles or response from others, we have to consider that the stubborn and chronic response we get is a response to our stubborn and chronic actions.

Or, as my mother always said, “It takes two to tango.”

Most stick/quit discussions revolve around this one, central problem: the other thing, person, project, job, or organization isn’t what I expected.

It won’t change. It won’t respond as I need it to. It’s taking too long. It isn’t what I thought. It won’t move in the direction I want it to go.

Yes, but have you changed? Have you increased or expanded yourself enough? Have you crossed over your own growth thresholds?

We grow and develop by confronting difficult situations. Worthy endeavors will change us. We will be stretched, challenged, and asked to change in profound ways.

So before deciding to quit (or stay) ask yourself how much you’ve  changed. Have you expanded your skills, abilities, attitudes, or sense of self sufficiently, to do what is required to succeed with this challenge?

Or is there something more you need to do, develop, or become?

That’s the first question. But you need the next question as well:

Is It Changing You In a Direction Aligned With Your Growth?

If you answered “yes” to question #1, the very next question has to be: Are you changing in a direction that’s right for you? Is what’s being asked of you in alignment with your deepest nature and purpose?

If not, then you will resist the changes being asked of you. And if yes, if the changes you are agreeing to are truly aligned with your purpose, then even though things will be arduous, you will have energy for the effort, and joy along the way.

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 a perfect fit.

The project was difficult, and to get through it, I had to change in a direction I valued.

So if you’ve answered yes to these questions, then maybe it is time to stick. But if not, maybe it’s time to walk away and consider where to next.

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

As always, thank you for reading.

I wish you all the best for the coming new year. And however and whatever you celebrate this season–or not at all–I want to take this opportunity to thank you for being a reader of this newsletter. I consider it a true gift to be able to share my thoughts with you.