What Is It We Love About Someone Quitting Their Job?

My friend Chris had a perfectly good, secure, well-paying job as a chemist up until a few weeks ago, when he quit. When he announced it on Facebook, he received a virtual round of approving applause, hundreds of likes and 100-plus comments. A few hours later, he logged back on to say thanks, and that he never thought that his resignation letter would be his most popular post ever. (he also fixed the typo in the letter before sending it, FYI)

I clicked “Like,” too. I was excited for Chris. I knew he was leaving his office life and taking a chance on riding his bike, writing, and doing freelance social media consulting and seeing what happened. Everyone else, whether or not they had details about his next adventure or not, seemed to like it, too.

A few weeks later, another friend posted this, celebrating another person quitting their job:

friends email

I wondered: is this a thing? I mean, we all still love birthdays, engagement announcements, babies, and weddings, but we also have a thing for celebrating someone who walks away from a career and toward something else. It can be as simple as “I’m leaving my job to go live in my car and climb full-time for a while” or “I’m leaving Company X to start my own business, something I’ve always been passionate about.”

There are dozens of iterations of the American Dream, from owning a house to eating a cheeseburger with a hot dog on top of it, but most people would agree that freedom is a theme that runs through every variation—freedom to eat high-cholesterol meat sandwiches, or freedom to paint the walls in our kitchen hot pink. Freedom from a job we don’t like, or have just grown weary of, is pretty near the top of American Dreams, even if we don’t realize it until retirement. Who hasn’t found themselves thinking, in a long staff meeting, for just a second, about never having to go to another one of those staff meetings again? Daydreaming about owning a coffee shop, traveling, climbing five days a week, or finishing that stack of books that keeps piling up on our bedside table because we never seem to have enough time? Those people who escape become a sort of hero.

My friend Nick was an electrical engineer for years, falling increasingly out of love with his commute and the work, and brewed beer at his house as a hobby. Finally, he put together enough money to start his own brewery, quit his job, and said goodbye to the hour-long commute to the office. Three years after it opened its doors on South Broadway, Westword named it the Best Brewery Tap Room in Denver.

Not all new businesses succeed (the majority actually fail within five years), and most people who take off on an endless climbing road trip eventually end it to do something else with their lives. But they had a taste of that freedom, even if it was only for a few months. There aren’t too many people living without participating in the money system, so most of us work. But there is joy in celebrating the “fuck this” moment of leaving a job and starting over, whether it’s ours or someone else’s (and whether or not there’s a solid contingency plan in place). Someone is escaping the drudgery or semi-drudgery of a job, and they become a sort of hero to the rest of us.

In his 2013 book, Dead Run: The Murder of a Lawman and the Greatest Manhunt of the Modern American West, author Dan Schultz discusses our obsession with outlaw heroes. Obviously he’s talking about people like Billy the Kid and Butch Cassidy, but I think in a much smaller scale, what he says is applicable to the people we see ditching the secure career for something uncertain:

“The main reason the ideal of an outlaw hero resonates so broadly in our society, why we have created a peculiarly American variety within our broader national myth of the American West is that the Western outlaw hero is a twisted extension of core American values. The desperate outlaw on the run not only had the freedom of the free-roaming cowboy disengaged with society; he pushed back at subjugating social forces— the relentless press of civilization and regulation. … In cheering for the outlaw hero, we are making a psychological stand for freedom, standing up to authoritarianism and dehumanizing social forces.”

Our world has changed a lot in the century since Billy the Kid and Butch Cassidy roamed the West, and we gravitate to far different stories, and sometimes more relatable ones. While no one will make a movie about Joe in the next cubicle turning in his badge one day to bicycle across the country, or our friend Jenny who turned her after-work hobby into a full-time career, those people sure do make for good contemporary outlaw heroes—so much so, we can almost see ourselves doing it someday.


17 replies on “What Is It We Love About Someone Quitting Their Job?

  • Cam

    My focus has always been international, and before I retired I had a succession of overseas jobs that gave me at least the feeling, if not always the reality, of doing what you’re talking about here. And since retirement, when what I’m doing (or not doing, I guess) begins to get to me, I scratch the itch by doing short-term volunteer gigs abroad.

  • Rachel @ Betty LIVIN

    I think so many people feel stuck or trapped in their jobs, unable to pursue their dreams because of finances so to see someone else pursue their dreams and break free is inspiring. It took me 10 years to get the courage to resign and go back to school and its a very scary thing!

  • Ian M

    I just quit my chemistry job as well! I am currently traveling and climbing around the Northwest, and I cannot be happier.

  • Jen

    It was a year and a half ago that I somewhat spontaneously quit my comfortable job to do …. something (anything!) else. I expected the reaction of others to be along the lines of “You’re doing WHAT?!” but what I heard was more like “Yeah! Right on!”. And while I wasn’t looking for the approval of others, the validation felt damn good and definitely fueled the fire to get the hell out of there. And now I find myself encouraging others to do the same. Great post, Brendan!

  • Sean

    Freedom!!! Great post. I sure do get pumped when I see someone leave the cube to pursue a dream. It motivates me to pursue my goals. Even though I was lucky enough to keep my job (which I like) when recently moving to Denver to pursue the outdoors, it was a tough move. Bravo to those who have the courage to make even more drastic changes.

  • Kevin

    I was really happy with my life until I read this post and realized I’ve never eaten a cheeseburger with a hotdog on top of it.

  • Velosopher

    I’ve left various careers in various ways. The least helpful one was to quit cold and move to Taos with no plan for making money. I had the time of my life that summer—and then it got cold and snowy and the money ran out and I got into debt. Bad plan.

    The best way was going back to school, getting a degree in something fascinating (that sort of pays), paying my dues for seven long midlife years on the front lines of that field, and THEN quitting. I am a private practice therapist now, and my schedule, performance metrics, and future are entirely in my hands. I ride at least four days week (however briefly), start the day at my speed, and like my work a lot (headaches included). Pretty good life!

    If you *really* want to do it, it will happen—eventually.

  • Kevin

    I think they did actually make a movie about it. It was called Office Space 🙂 .

    Last year, (much like Peter Gibbons) I stepped away from a career in Software Engineering. I went to Nepal for a couple months and have been exploring different interests and visiting friends and family since. It took a long time to work up the nerve to walk away, but the response has been almost universally positive. Most people, both on the surface and on a deep level, feel trapped, and the idea of breaking free of all obligations and expectations is very appealing.

  • Ricardo

    In September it will be fifteen years since we walked away from the corporate world to travel. Contrary to popular belief, it doesn’t take as much cash, cajones or carelessness as some try to make it seem.

    Many of us are initially motivated by negative freedoms – freedom from – like the subjugating social forces mentioned in the quote. At some point we seem to fall in love with the positive freedoms – the freedom to – do the things we dream about.

    For more on the philosophical aspects of quitting see

  • Trail_Turkey

    The next best thing to quitting your job to roam full time is working for a boss who supports your hobbies. Last week I took a three day weekend to ride a bikepacking route. I checked in via text with my boss before I shoved off. His reply was ‘Enjoy the freedom.’ If I have to work for the man, he’s a guy worth the effort.

  • Manny Centeno

    Recently did this now I’m at month 10 of traveling/working seasonally. I’ve grown so much more than I had by owning a car, having an apartment, steady income. One doesn’t grow while living in a stagnant environment. You grow while immersing yourself in many different area’s of live. Seeing new things everyday, testing yourself mentally and physically. That’s how you grow. Becoming my own hero has by far been the most monumental lifestyle change to this day. At the ripe age of 26, I’m pretty excited to see whats next. Thanks for all the writing and insight you give us Brendan.

  • Kevin P

    I pulled the plug on my job in 2011 and started living the dream’. However… ‘living the dream’ has lead not to New Zealand for years at a time… but instead to REALLY tie myself down by starting multiple businesses and now working harder than I ever did before. (but… I do cool things and still travel… so I can’t complain!)

  • Katherine

    Great piece. I think some of it has to do with our collective failure of work-life balance (read about how many people don’t take all their vacation days each year). I have watched this in my mom, a doctor who used to do very little other than work (my whole childhood). A few years ago she went to teach at a medical school and has spent the past couple of years scaling back so that she’s no longer working 100-hour weeks. Suddenly, she can have a life, too, and it’s transformed her into a much happier, energetic, healthier, easygoing person. She exercises, travels, has new hobbies, has strengthened friendships and, in fact, is so damn busy having fun and going on little adventures that I can barely get ahold of the woman on the phone (like flying to Connecticut for the long weekend to go sailing with a friend). I am so proud of her, and admire what she did as much as I’d secretly admire those who fuck off for a little while after enduring the rat race. I also admire her because I am like her: too practical to ever give up a “real,” productive job. I could never do the live-in-a-van-by-the-river thing, but I learned from watching her wait nearly 60 years to be happy and have instead pursued my passions through my career from the start. The money is not good via that route but, hey, my happiness means I’ll stick around. 😉

  • Jennifer

    The first job I got after graduating was a corporate finance job. I knew a behemoth, billion dollar, government regulated company wasn’t the right when I accepted the job, but wanted the experience anyways. I knew I wasn’t enjoying it while I did it, but I didn’t quite realize how it was sucking the life out of me until I quit, 14 months later.
    The day I quit was one of the most empowering days of my life. As young 20-somethings, almost every decision of our lives so far have been somewhat mapped out for us. Oh, you graduated middle school? Great, go to high-school. Oh, you graduated high-school? Congrats, time for college. Oh you’re a senior? Apply for jobs and make sure you have one by the time you graduate. I felt a lot of pressure to stick it out in this job to “get the experience, get the reference, etc”.
    But then, for the first time in my life, I got to make a decision all by myself that dramatically changed the trajectory of my life and completely changed how I spend the majority of my week.
    I still have a job in Finance, but it’s for a small start-up company. Every single aspect of my life has improved. I’m climbing harder, weekend-warrioring harder, leading more climbs, started running again, and I’m sure my boyfriend would attest to the fact that I’m also much nicer to be around.
    This article gives me goosebumps, because I’ll never forget how I felt the day I put in my notice, with the song “Take This Job and Shove It” stuck in my head on repeat.
    Quitting my job was one of the most rewarding things I’ve ever done.

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