When to quit

How to spot a turning point

I used to be addicted to quitting.

The more I did it, the easier it became. A job, a relationship, an apartment, a city: they were all as easy to leave as they were to enter.

I didn’t see any downsides, just a swell of adrenaline and a new taste of freedom.

I was a glutton for new experiences and leaving one thing meant welcoming in the new. Any new, I didn’t really care.

I suppose I kept waiting for life to begin, so quitting was an easy way to create a beginning.

I was a fervent devotee of the fallacy of ‘arrival,’ believing with all my heart that ‘As soon as I get/do this one thing, I’ll finally be happy.’ I ping-ponged around Chicago neighborhoods and then to South America and then to every coffee shop job in the greater Chicagoland area and then toward love interests I thought would take away all my insecurities.

But I started noticing that moving to Chile didn’t make me a completely different person, and getting a slightly better job didn’t raise my self-esteem, and chopping off all my hair again didn’t make me any braver, and treating people like disposable personality traits I could try on for a time wasn’t fulfilling for anyone involved.

A picture that captured this time so well: deciding where to live next and growing out one of my compulsive haircuts

And then….long story short, I learned commitment.

I had my first ever long-term relationship, which was my decision to draw and post an illustration on Instagram every day. I didn’t always want to do it, but I did it anyway, for years. I learned a lot from that.

But I also started forgetting how to quit. What came so easily and naturally at 23 felt scarier with more at stake. In every area of my life, I didn’t know if I was allowed to leave. (No idea who I looked to as the keeper of the permission slips, but it sure wasn’t me.)

A Younger Me with short hair and a constantly-changing address had been waiting for life to begin, while Current Me felt like life had begun a long time ago but I had missed the start buzzer and I was still scrambling to catch up.

New beginnings felt fun at 25, but sort of pitiful now.

Neither the Quitter Me nor the Committed Me were fully in touch with my intuition. In fact, I think the constant quitting and the over-committing were both tactics to avoid my intuition entirely, because I wasn’t ready to hear what she had to say.

But then I started listening.

Scratch that, I paid a career coach an ungodly amount of money and doubled up on therapy and talked every friend’s ear off for a year until I was finally able to say, but only in a private journal entry, “I’m allowed to quit Instagram.”

And then my intuition was like “Omg congrats Sherlock, I’ve only been trying to tell you this forever, good job outsourcing your instinct and forgetting I exist as the deepest wisest most ancient part of you. But what else is new?”

And then I remind my intuition that I live in a society dominated by the masculine demand for explanation based on external facts, rather than the feminine value of mystery fueled by inner wisdom.

My intuition rolls her eyes. I tell her I’ll do better next time.

So, to honor her, here are three ways that my intuition has tried to get in contact with me while making a decision to quit.

And if you’re like me and need a permission slip from an abstract entity, I’m here to tell you that you’re allowed to quit/leave when:

You want to

This is an underrated reason to quit, but a perfectly valid one. You want to stop? Okay then, stop.

It’s possible you’ll regret it. It’s also possible you’d regret staying any longer. It’s possible you could have worked through the hard stuff. It’s also possible you’re better off for not having endured them. You might have an epic story of triumph if you stay. But you’ll most likely have a better one if you go.

When deciding whether or not to break up with a perfectly good boyfriend, a friend of mine said, “You might meet serendipitously on a street corner in London, ten years from now, and realize what you lost. But for right now, in this moment, at this second, it’s time to go.”

As Cheryl Strayed says in this essay which I recommend you read instead of this one, “Wanting to leave is enough.”

And you don’t owe anyone answers. Just say you’re respecting the oft-ignored feminine power of instinct. :)

And listen to this song, which is about leaving a romantic relationship for no particular “good” reason, but could also work for any chapter you want to close soon:

Hold these words in your sternum (a part of your body that is etymologically connected to the word “sacred,” because that’s where the holy intuition lives):

I won't be far from where you are if ever you should call
You meant more to me than any one I've ever loved at all
But you taught me how to trust myself
And so I say to you, this is what I have to do

'Cause I don't know who I am, who I am without you
All I know is that I should
And I don't know if I could stand another hand upon you
All I know is that I should
'Cause she will love you more than I could
She who dares to stand where I stood

You’re in someone else’s dream

Two years ago, I got a Christmas card from a dear cousin who I haven’t seen in eons.

“Congratulations on all your success,” she wrote, “It’s amazing to watch you get what you wanted.”

It was such a sweet sentiment, I held the card to my sternum. But then I started crying like there was no tomorrow.

I kept thinking, through the guiltiest tears I’ve ever shed, “This isn’t what I wanted.”

It’s so counterintuitive to quit when we tell ourselves, “But anyone would want this—I should feel lucky.” It’s really tricky to leave when we have a dream job that isn’t our dream job.

You can be dating a really spectacular person who isn’t your person.

You can live in the greatest city that isn’t great to you.

You can leave a job that someone else would want, because you don’t want it.

I remember having a crisis of self when I was in college and people were constantly asking me what I wanted to ‘be’ and, being the sweet little bleeding heart liberal with OCD I’ve always been, I thought “I’m not allowed to have a dream job, because most people in the world can’t have a dream job.”

It took me so many years to realize that wanting a beautiful life for myself didn’t take beauty away from other people.

This really sunk in when I had Guillain-Barré Syndrome and I was paralyzed, and so many well-meaning friends wouldn’t tell me what they were up to because they thought I’d be too jealous.

And yes of course I was definitely jealous!!!!!

But the only thing worse than jealousy was resentment. If I asked a friend what they were up to and they responded, “Oh nothing, just watching TV,” I’d get furious.

How dare they waste perfectly mobile legs on SITTING, when I would be auditioning for the Olympic javelin team if I could move!??

I learned that humans (at least this human) didn’t want to bring others down in order to make the world equal. What I really wanted was for people to make the most of what was handed to them.

So I allowed myself to start dreaming, and I let myself say “no” to opportunities that someone else would want, and I gave myself permission to think, “I have a good life, and it can get better.”

Someone would want a lot of Instagram followers, but I don’t. Someone would like to take a paid partnership with a caffeinated sparkling water beverage, but I wouldn’t. That doesn’t make me better, and it doesn’t make me ungrateful. It’s just someone else’s dream, and I want to get back to mine.

It got hard

When I started posting on Instagram, it felt like entering a clunky coffee shop where everything was a little off: the ‘Open’ sign was askew, the baristas were still learning the differences between espresso drinks, and all the chairs were mismatched. But it was comfortable: I knew the crowd, I knew my order, I loved the music, I got to work.

I made art for the pure hell of it, and folks either glanced at it or they didn’t. I sipped my latte in the thick ceramic mug no matter what, happy as ten clams.

And then one day—I’m not sure exactly which day—I came into that familiar, rustic, wacky coffee shop, only to find a slick espresso bar in its place.

Everyone there asked why I was there, and then they started asking to see my art and assess whether it belonged or not. The baristas wore suits and sunglasses, and they made me feel bad about my order.

As I created art in that space, I felt the gaze of people who were only there to judge…but then gave me their business cards as they left.

A once-comfy place felt sterile and scary. The handwritten signs were replaced with (dun dun dunnnnn) labels in Helvetica.

This is how it can feel when something you once loved morphs into something that is very difficult to love.

Difficulty in life is normal. Challenges are normal. But when it requires huge strain (and maybe even a complete personality change?) to navigate, it’s most likely time to quit.

Relationships don’t have to be hard. A job doesn’t have to erode your soul. A commitment doesn’t have to take everything from you. Even if any of these are “okay,” your soul will tug on your sternum when it knows there’s something easier, or more aligned, or more life-giving for you.

And it takes a lot of wisdom to know when to abandon something that has been working for a while.

I was just watching a documentary about Bill Gates, who said that it’s going to take a lot of innovation across many industries to properly address climate change. And, this means…many failures. It’s going to take a lot of failure.

It takes failure to find our most aligned job, our soulmate, our community, our ideal home. And even then, because we are human beings and not Sims characters, we probably won’t get it totally right. Actually, I think we’re doing a great job if we get it like 20% right.

If you’re discerning whether or not to quit, my hope for you is that you will have a good convo with that deep intuition that lives in your sternum, and you can rely on wisdom that predates your existence in order to set an expiration date for this chapter in your life.

If you’d like more on this topic, I wrote on decision-making here:

PS. I have two retreats coming up in 2024: One in North Carolina, and one in Wyoming!