Breaking up with your job is like breaking up with your mildly okay boyfriend

Your job treats you decently. It only makes you cry once a month or so. It provides you shelter and food. That’s all you should want, right?

In the layer upon layer of conversations I need to have at the giant bureaucracy where I work, I’ve come to understand that quitting is very unusual. The generation before me has had these jobs for 20-30+ years. So the idea that I would NOT want this life is entirely hard to swallow.

I’ll admit, these coworkers and bosses make persuasive arguments – until I talked to my friend, and she said:

“It sounds like you are trying to break up with a bad boyfriend.”

Amy Poeler wrote in her book Yes Please that you should treat your job like a bad boyfriend. Your job won’t be there to comfort you when you need it. It will just suck everything it can from you if you let it.

I am weak here – I keep getting sucked back into the conversation with my mildly-okay-boyfriend-of-a-job and have spent days going in circles.

imagine listening to this nearly every day. it’s a miracle my friends haven’t broken up with me.
imagine listening to this nearly every day. it’s a miracle my friends haven’t broken up with me.

I am on to the game. I’ve broken up with mildly-okay-but-clearly-not-right-for-me boyfriends before. It’s just really hard because once you start that breakup, mildly-okay-boyfriend sometimes switches to clingy, bad boyfriend to get what he wants.

Bad Boyfriend/Job Argument #1: I’m as good as it gets, baby.

You’re here, I’m here. I treat you decently. Yes, I demand most of your energy and don’t leave you time for doing things other than what I want, but that’s what a job is, sugar cakes.

This job does treat me well for the most part. Maybe this IS as good as it gets – aside from the occasional flash of misogyny. Am I kidding myself by thinking there is a different way? That I too can live like a Swede and work only 30 hours per week and have a better-balanced, full life?


Bad Boyfriend/Job Argument #2: No one else is going to want you like I do.

Pumpkin muffin, you can be a little difficult at times, but I put up with you. We’ve been together so long, I know your quirks and I accept them. But do you really think you’ll find someone else who will put up with all your stuff?

This is the ultimate fear: If I quit, no one will ever hire me for a job ever again. How can I possibly explain this gap on my resume in the 25 seconds a recruiter will spend looking at it?

bad bad boyfriend.
ok you’re not THAT great, bad boyfriend.

Bad Boyfriend/Job Argument #3: Others want me real bad.

Honey bun, I already have five others in line who want your spot. If others want me so bad, it clearly means you should want me to. What’s wrong with you for not wanting me?

Don’t you need me in the long run anyway? You know you’ll just want me back.

And they are right, it is possible! Maybe I will want this job back again! How can everyone who wants this job be wrong vs. just little ole me who isn’t sure if I’m right?

The Washington Post wrote in today’s paper that maybe a recession is coming. What if I quit and there’s a recession and I can’t make this work and I never have a job again and I have to go back and live with my parents!?! Maybe I SHOULD stay.

can change

Bad Boyfriend/Job Argument #4: I can change, I swear.

Baby, what if I change just this one little thing about me? What if I promise I’ll let you go home at 5 every day, or even let you work from home some days? Just tell me what you want that’s different and I’ll do it. Mostly. Kind of.

Hold up! Deep breath.

I’ve done this before. I can do this again.

I know the only way through a breakup is to gather close as many supportive friends as you can find. You buy them drinks in exchange for having the same conversation over and over again.

So when I talk to my friends about my daily doubts, they say:

“Stick to your guns. Affix said guns to your hands with glue.”

“You deserve better. Just because others want it, doesn’t mean it’s right for you. When you do find the right fit, it’s easy and wonderful.”

“You don’t want to disappoint your whole 48 readers on pentraveler by going back on your awesome plan.”

Re-read your Post No. 1.”

“You’ve planned for this. You know you can do it. No decision is forever if it does turn out to be a mistake.”

“I’m so proud of you. I support you.”

And lo and behold, I can breathe again.

Nine weeks!

5 Reasons to Leap – and 10 weeks until I’m quitting my job

In 10 weeks, I am quitting my job, leaping out of the career race that is Washington, D.C., and boarding a plane to Chile.


Look, this has NOT been an easy decision. I’m in my mid-30s and have been on a fantastic upward trajectory in my career. I believe in Lean In. I spent the last year of my life working 70+ hours per week on a massive priority project, prepping my boss for meetings with the Big Guy, and it’s been incredibly rewarding.  My career is important to me.

But at some point in the last six months, I realized my life has pretty much looked like this for several years now:

toomuchwork_pie chart 2
i worked 110 hours one week. seriously.

Sure, I’d take vacations once in a while. But something wasn’t right.

I couldn’t stop thinking about certain pieces of advice I’d heard from mentors and articles the last year.

  1. Unwitting Mentor: What do you love so much, you could do it every day, without stop, forever?

Everyone has something like this, but so many of us have lost it. It’s usually something you did non-stop when you were little. Maybe it’s being outside in the sun (and now you’re in a windowless cube), or sketching, or playing a sport, or reading or baking. You know what it is. That thing that every time you do it, you disappear into the zone, hours pass, and you are at peace.

This advice came from Elizabeth Theranos, who I think is one of the most amazing and talented women alive today. She worked nonstop on her invention for years on end. She loved it so much, there was nothing else she could do but this. (Of course, she eventually got to her goal and now is a gabillionaire, but money isn’t the point here.)

Probably most of us aren’t built like that – I know I’m not – but there are things I love so much that I would like to do every day, and I’ve lost over the years. Like writing for pleasure, and not for work.

Here is a cover and a page from a “book” I wrote at 8:

my writing has improved thankfully since i was 8


2. Fully Aware Mentor: What stories do you want to tell from your rocking chair?

How you won that big account of a paper company and your grandchildren don’t even know what paper is now because it was obsolete by 2030? Or how you wrote a billion papers that were used for a total of 10 seconds in some meeting once?

Or do you want to talk about the time that you ran from a bear, you almost drowned learning to dive, or that person you loved but just wasn’t right for you? That you explored the world and made huge mistakes, but you don’t regret any of them?

I don’t know if I want to have grandchildren of my own, so I’m not entirely sure who will listen to my stories, but I definitely want to be talking Big Adventure. Big (more, already made plenty) Mistakes.

  1. Random Online Quote Mentor: Make new mistakes. Do what scares you.

Making mistakes is scary. I don’t think you can be human and not fear making mistakes and being judged for them.

This is probably a healthy emotion to a degree, but you have to know at what point it stops being a positive – don’t-go-down-that-dark-alley-alone-it’s-dangerous – and turns into a negative – don’t-try-purusing-that-thing-you-love-because-it’s-new-and-different.

Letting fear hold you back leads to only one thing, as far as I can tell – regret. Whether it’s starting something new or leaving something, it’s the first step that is the most terrifying.

In fairness, I’ve quit a job previously and gone to travel. It was one of the best six months of my life.

nortern peru valley penwriter

But to do it now, when my career is going so well, when everything and everyone around me is telling me to settle down, buy a house, have a family, keep that steady job and keep advancing it?

Very scary.

  1. My Mentor (and Unwitting Love) Mark Manson: Just don’t give a fuck.

I need to be honest with myself: I don’t want to be judged.

It’s kept me from making decisions before in my life. I do care what people think. And not just my family and friends, but random people I’ve never met who might theoretically learn something about me and think it’s stupid. Yea, I’m that scared of judgment.

Unfortunately, you can’t avoid it. People are going to judge you. Whenever you do something out of the norm, you’ll hear or see a reaction.

Which is why I love Mark Manson, who writes that learning the difference between when we should and should not give a fuck is essential to being comfortable and honest with yourself and others. It’s tricky. But worth it.

Unfortunately, Mark is not single as far as I can tell, so I will continue to love him from afar and recommend his articles to anyone who will listen. (Especially this one on relationship myths.)

  1. My Closest-Thing-to-a-Life-Coach Mentor: Visualize your two futures.

Fair warning: My friend called this technique “very Portland-y.”

Picture yourself, 10 years from now, having made one decision, on your current trajectory. Build that full picture in your mind – the job you’ve achieved, the office, the car, the family. Or maybe it’s a relationship or a place you live.

Did you feel something good in your body? Maybe you sat up a little higher, or smiled, or relaxed your shoulders? Or did you feel a twist in your stomach, a frown, or a claustrophobic sense of breath?

Now picture the other choice and the future it’s created in as much detail as you can.

How does your body respond to that future?

Your body already knows the answer.

Mine knew. It was time to leap and create a new future from the path I was on.

So I drew a new chart, composed of the kind of stories I want to tell on my rocking chair.

better life pie chart 2

Even now, sitting with my decision made and out in the open, I am scared some of the time. And I feel the weight of judgment some of the time. But after a few minutes of indulging those some of the time, I either call one of my friends who supports me 100% for a pep talk, or I look at the cover of my Chile travel book.

liz lemon i want to go to there chile_book

I am to go to there.

Or I sit and write and two hours have passed and I’m happier than I’ve been in weeks because I’ve been doing something I love.

Because this life has to be about more than just work. Starting a new path will never be easier – a lot of planning and saving, yes – but the timing will never be better.

I can do good, meaningful work, AND have a good life. I am convinced.

So I’m leaping.