I wanted to quit.

But I wasn’t allowed to. 

I was about 6 years old and in the back seat of the car, wearing a polyester Little League uniform. My mom was driving me to practice. 

Please Mom, I don’t want to go. 

I hated Little League. That stupid rubber tee with the ball perched on top. The way the smelly, too-big helmet wobbled on my head when all the ones my size had been taken by the other kids. The debilitating boredom of standing out in the field waiting for someone to hit the ball toward you, to please just get some action, any action at all … 

Plus, I was not very good at Little League. I was not good at throwing. I was not good at sprinting from one base to another. I could never hit the ball as far as I imagined I could. 

I had been begging my mom to quit for weeks. 

No, she insisted. Once you start something, you need to finish it. It’s important that you see the season out. 

The memoir I’m writing about taking a sabbatical year, at its core, is all about quitting. Quitting one life in hope of finding a better one.

Recently, when I was excavating my memories for why it felt so hard to quit at 34 years old, this story emerged.

I respect my mom for what she wanted to teach me with softball: The importance of following through on our commitments. Perseverance is probably one of the traits I have that I value most in myself. She really modeled that for me.

Yet what I now know is that you shouldn’t always follow this rule.

In fact, we might be better off in life if we quit more often and sooner when something isn’t working for us.

Why Quitting Can Feel Taboo

About a year ago, I wrote a blog about how as a coach, I help a lot of people to quit their jobs. I remember that it kind of felt dirty to say. Like I shouldn’t say that publicly even if it was true. It was too transgressive.

There are a lot of taboos around quitting. 

I’ve been really enjoying reading Annie Duke’s book, Quit: The Power of Knowing When to Walk Away. It feels really powerful, like the perfect companion book to my work. 

It’s also a very forceful and well-researched rebuttal to all those taboos. 

Annie Duke is a former professional poker player, which makes her an excellent person to write about quitting. It turns out that to be successful at poker, you need to be really good at knowing when to quit. (Kenny Rogers knew what he was talking about.)  

She supports the idea that quitting is “integral to success” in both your personal and professional life. 

She talks about how when you get the feeling of when to quit (you know, when you think: “that’s ENOUGH! I’m outta here!”) and how it’s actually probably way past when you should have quit. 

She also talks about all the forces that go against “good quitting behavior”, like social taboos, the desire for certainty, and commitment bias, which is our tendency to remain committed to our past behaviors even if they’re proving not to be working out for us. 

My Best and Worst Quitting Moments

Looking back over my professional life, one of the quitting moments I’m proudest of is when I went into a job interview in my early 20s and the hiring manager – after a few initial questions – asked me, “How do you feel about being on the phone for up to six hours a day?” 

To tell you the truth, I did not feel good about it at all. It sucked because I had really been excited about this job opportunity, but when she was being upfront about what it really consisted of, I realized I was going to be upfront too. 

I looked across the table at her and I said, “You know what? I’m getting the sense that this isn’t the right job for me. I appreciate your time. Thank you.” 

And I stood up, shook her hand, and walked out onto the street with the sweetest sense of freedom I’d ever felt. 

Contrast that to the quitting moment I am least proud of (and am writing about in my book): taking 3+ years to quit my job in international development, waiting until I was 100% certain that I had to leave. 

The problem is that 100-percent certainty that you need to quit is a very painful place to reach. 

By the point that I actually quit, I felt burned out, sad, out of integrity, and totally lost. 

Are You Ready to Quit?

If you know that it’s time for you to quit, and you’re somewhere between these two extremes, first of all, no shame in it. Don’t worry. This is a very human place. 

If you could use some help right now to quit, here are some concrete ways I can help: 

👉 First, I’m here to listen – from an outsider point of view – as you lay it all out. I then reflect back what I’ve heard, especially the places where you have a lot of energy and or the things that get repeated and emerge as themes. Usually, this back and forth process brings you a lot of validation and clarity.

👉 Then, I can help you to see all that you can gain by quitting, including all the possibilities and opportunities that you’re missing out on by staying where you are. I help you to start making future possibilities more real and tangible through investigation, communicating your plans to others and bringing them on as support, and through taking intentional action.

👉 I’m also here to encourage you and to keep you accountable … if your courage falters.

There is a lot in our psychology, our culture, and our upbringing that often makes it very, very hard to quit.

There is also so much to gain from quitting.

One of my biggest inspirations in this work is when I witness others freed from things that were not working for them and stepping into a new way that does fit them and lights them up.

Stunning.

It’s like the opposite of me in a white polyester little league uniform taking a swing at a ball perched on top of a tube.

I would have dug up a photo of that for you but I think they’re all in my mom’s basement.

Anyway, I quit that, so we don’t really need to go back there, do we?