The Comfort of Moving On (When to Quit)

A few years ago, I heard former professional gambler and author Annie Duke on the marvelous podcast, “People I (Mostly) Admire,” hosted by economist Steve Levitt of the Freakonomics franchise. In Duke’s book, Quit: The Power of Knowing When to Walk Away, she discusses the art of quitting, and how many of us wait too long to walk away. After all, if there’s one thing a good gambler knows how to do, it’s “when to fold ‘em,” as the song goes. It’s important not to stick with a poker hand when the odds are telling you to quit.

Similarly, it’s important in life not to stick with a job, a pursuit, or a partner when every fiber of your being is telling you to get out. Steve Levitt summarizes Annie Duke’s book this way: “People stick with bad things almost always for too long, and we’d be better off if we quit things sooner.” Waiting too long causes us to stop progressing, to stop gaining ground toward our goals.

How often have you waited to quit an unfulfilling job out of fear and uncertainty, only to find that after doing so, you wound up telling yourself, “I should have done this years ago”?

Getting yourself to quit on time can be tricky. There’s an emotional pull in our society that makes quitting sound weak. We hear accolades for people’s “stick-to-itiveness.” We hear aphorisms like “quitters never win, winners never quit.” But what we might not hear is that a successful person who you admire might have quit three other goals before finding the one that worked, that an entrepreneur had two failed businesses before finding the one that succeeded, that a person left three romantic relationships before finding the one that clicked.

In order to grow, we have to allow ourselves to quit aspects of our lives that aren’t working.

Over the last year, I quit my two main music activities: I stopped playing at a church where I’d worked almost every Sunday for twelve years, and then last week I played my last concert with a local yacht rock band that I’d performed with for three years. In both cases I was playing with good musicians who were nice people. There was nothing awful happening in either scenario. Both allowed me to do what I do fairly well: play the keyboards. Both paid me a little cash that gave me a sense of contributing to my family (albeit, minimally). There were reasons to stay.

But neither musical act was fulfilling. I wasn’t inspired. I wasn’t stretching myself as a player. I was showing up, playing, collecting a check, and going home. That’s not what I want out of music. I think of drummer Bill Bruford quitting Yes, Gregg Rollie leaving Journey, or Sting pulling out of The Police, each at a point when those bands were at their creative peaks. There were all sorts of reasons to stay, but they each decided it was time to walk away.

Now, leaving a church gig and local yacht rock band pales in comparison to the above examples, but despite a multitude of reasons to stay, I quit both of them, and if I’m honest with myself, later than I should have. You know you’ve made the right decision when after quitting you feel a little lighter, a little freer, and that’s how I feel now.

Now it’s up to me to put that new energy into action, and to proudly carry the mantel and say, “Yeah, I’m a quitter.”