Why Do We Love Someone Quitting Their Job?

Hey, if you’re stuck in a staff meeting right now, read this and pretend you’re checking your notes.

My friend Chris had a perfectly good, secure, well-paying job as a chemist, then 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.

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:


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.”

Photo by jbdodane


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Brendan Leonard is a contributing editor to Adventure Journal. Follow him at his blog, Semi-Rad.
Showing 21 comments
  • Tim

    …and now Chris finds himself mountain biking in Nepal. We all have to make our plans and set a date to chuck it all. If only we could move that date up a bit… or a lot!

  • Lindsey

    I recently did just that…quit my job as a doctor to move across the country and start my own online business. The outpouring of cheers was incredible from people who I haven’t talked to in years.

  • Rosien

    Great read,and I have noticed the same, although in my circle it’s more that people are anxious to start a career. Younger I guess, you can’t quit a stable job if you’ve never had one. I know from experience how terrifying it can be to embark on an infinite trip, or to follow your dream, so petty as it may seem, those likes and comments are definitely worth something.

  • Pedro

    I recently enjoyed an early retirement. I was fired (for non-disciplinary reasons) and once I got over being fired for the first time in my life I embraced my year and a half of freedom. I didn’t go on a road trip. I did the things I had on my life list that I never really expected to do. I re-modeled my house. I ran or mountain biked or climbed everyday that I wanted to. I read books. I volunteered at my kids schools even more. I lived a life I wanted to and am so happy I had the chance because now I make decisions based on this experience rather than what the bottom financial line might say…even though I have a real job again.

  • Jon Canuck

    Not just the American Dream. As a 30 year-old Canadian, I dropped out of a ‘career’. Traveled broadly, seasonally settled into mountain towns across western N America. After 10 years, I returned to school in a field I had a passion for: forest ecology. After 17 years out of a career track, I knuckled down to 20 years in applied forest ecology. Now retired, age 70. In retrospect, I wouldn’t trade those 17 years of freedom-adventure-travel-schooling for anything.

  • Erik

    While I admit that there is a vicarious liberation that comes with these events, they also smack of privilege. It is a lot easier to be carefree when there is a huge safety net beneath you.

    • Joe

      Erik – I fully agree… but it’s also hard to not come off as being jealous or bitter when we accuse others of being privileged. However, I do find that when I hear stories like this, most often the person who’s taking the risk does indeed have a huge safety net, with parents and/or family who are pretty well-off and they know they can afford to. Me, my parents were both born in 1929 (my Dad was born 3 days before the market crashed and the great depression started). Needless to say, we didn’t have much money growing up….. we weren’t poor, but we were let’s say solidly “lower middle class”. No savings accounts, no vacations, but we didn’t go hungry. I was the first person in my family to ever graduate from college and I’ve always been risk-averse to taking chances like this because frankly, I can’t afford to. I have NO safety net, zero. My Dad long since passed and my Mom is 86…. when she finally goes, I’ll inherit what she’s got, which is under a thousand bucks. Heck, I hear some of the millennials in my office joke about blowing more than that on a weekend at the beach…

      I’ve always dreamt of quitting the job and roaming the country, climbing mountains and riding my bike. But I simply can’t. It would be beyond irresponsible because I have no net to catch me, besides the public dole. And I’m far too proud for that mess.

      So while I agree with you about how most folks have a safety net and it makes these choices WAY easier and less risky for them, I try not to hold it against them. It’s not their fault that the baby-boomer parents and parents after that generation are the richest parents in the history of the world, by aggregate. It just is.

      • Filibuster Cash

        I’m not sure it’s bad to be bitter about this sort of thing. It’s never people making $10 an hour with $53 in their life savings doing the leaving. If that were possible, nothing would ever get fixed or cleaned or cooked in this country. It’s always “I left my job as a doctor” or “my career as an engineer left me unfulfilled”. I can’t afford to think about fulfillment, and no one I know can, either. We all just want to pay rent. (Definitely not buy, cos that’s way above my paygrade.) Still, go ahead and leave that job an education I can’t afford got you. Just don’t expect my help when your tire goes flat on the Sprinter van you’re using for that unending search for self.

  • Dan

    What would you do if you knew you would never starve or freeze to death? I don’t personally know anyone who has starved or frozen to death, but I know many inspiring souls who faced their fears and finally said what do I really have to lose. Those are the ones who gained so much. It has nothing to do with privelege, money, or certainty. Be creative and know at the end of the day that only you are responsible for your life. Figure out what it is you want, and go do it…

    • Erik

      Dan–I totally agree that challenging oneself is essential, be it physically, intellectually, or just improving one’s life. I couldn’t tell if you were suggesting so, but I like to differentiate between challenge, and going to live the dirtbag lifestyle in Baja, maybe starting up a GoFundMe site to support oneself. While the lines can certainly seem blurry, I think that there is a difference between truly challenging oneself, and making a lifestyle change because one doesn’t like being stuck in an office. In some way, that could be viewed as the anti-challenge. Sure, I’d rather be hitting some sweet single-track everyday, rather than spending so much time sitting at my desk, but I find it challenging to maintain my focus on helping OTHERS through my work, no matter how mundane it can seem sometimes. I think that there is a misconception that tedium makes us a “slave to the man,” however escapism solely for personal gratification is hardly a challenge. Leaving a well-paying corporate job to go teach in a community that can’t attract teachers–challenge. Leaving that same job to go surfing–not so much.

  • John keith

    Pirates and heretics rock!

  • Mike H.

    Good insight, Erik. But those with privilege needn’t necessarily wear a Scarlet P. The doctor (above) could keep on raking it in, but instead she chose to take a less “sure” path. I think there’s something to that… something vulneable and inspiring. Regardless of one’s socio-economic background or current reality, I’m a big believer in heading off on the occasional FIAT (fuck-it-all-tour).

  • Jwesener

    This totally resonates with me. It’s like being a POW and seeing someone escape. I don’t really consider starting your own business as escaping, more like trading one prison cell for another. Those who take off to adventure, tho…

  • Bruce

    While I dream of adventure and have a certain respect for the risk takers who chuck it all, I work every day to pay taxes, support health care, earn health insurance and pay my due share to social security. I do not set my “dreams” aside so that someone who was gainfully employed but chose to leave that security behind can go on the public dole due to catastrophic illness or injury or seek public assistance when their dreams fall flat. Sorry we all have to work as a part of our social contract and to support the LESS fortunate among us.

  • The Seeker

    At the heart of the matter is fear. When I quit my job to search for something more, it was not the result of having a large safety net. It was the recognition that my life had come to a cross road and I had to escape in order to grow. If you think about all of life’s real moments, when it comes down to it, all of us can change if forced to by sickness or trauma. I wanted to not wait for that to happen and instead took a leap of faith. After six months I came back into the safety of full time employment, and then spent the next 17 years building a career. I have never forgotten the fear and freedom of that time. It has warmed my heart and I believe now I could do it again with careful planning. Maybe sooner than I expect. One place that has helped me with fear, is the bible. Not to get religious on you but it talks about fear in very enlightening ways and has helped me put my fear into the right perspective. Any time you quit your job, a spiritual journey begins…we don’t always realize that. I am convinced that is why we are drawn to these stories because we know deep inside we could devote time for neglected matters of our mind, body and spirit. A job does not often address those matters.

  • Ryan

    those of you who speak of only the ones chucking it have a safety net are simply afraid of failure.

    I chucked it all with 4,000 dollars of savings, from a furniture sales job (a meager living). no help from anyone, student loans, car payments etc. supported my fiance and I for 4 months of traveling living out of cars and on couches. I ended up running out of money and taking a job as a wilderness guide and making an even more meager living. Not wearing a suit and tie, barely making rent, driving cars that have 200,000 miles on them teach you to be resourceful, and you learn quickly money doesn’t do it all for you.

    In my parents eyes I failed. In my eyes Ive lived fuller than 95% of people I know.

    Safety nets don’t have to be made of money, they can be made of knowledge, drive, and happiness

  • Barry

    A good read and it rings true.

    It took me over 10 years to realize I was at a dead end job. I didn’t have a plan but I had been saving to buy my own place for a long time. I couldn’t suffer a new boss and I was reasonably confident that I could find another job so I took permanent vacation. I received several “attaboys” and heard several “I wish I could do that” from friends and colleagues.

    One of my skiing buddies has been fishing commercially for years. Whenever I would bitch about my shitty job he would tell me to quit the job to go fishing. After I quit I hit him up about the gig but the boat was all crewed up. The next year as I was moving cross country to live with a GF I got the call about the greenhorn job in Alaska. I just finished my second season fishing and it was a near record haul. I can’t tell you how many people have hit me up about getting on a boat. Whenever I am introduced to new people, friends like to mention that I am a commercial fisherman. Nobody was ever impressed by my previous “profession”.

    I feel bad for anyone that feels trapped in a job, good luck finding a way out!
    The only regret I have about leaving the old job is that I gave no notice. My old boss was a good guy and I should have called him but the new guy drove me insane.

  • juliette

    After 10 years of the seasonal, rambling and adventurous life, I’m trying to travel in the opposite direction. And wow is it different. Now that I’ve decided it’s time to switch gears, get a “real job”, it seems the life I thought my degree and education would provide was all a mirage suddenly decayed by the time it took me to arrive. Now I’m just older, inexperienced and feeling mighty worthless. The electrical engineer leaving to start a brewery doesn’t have to fight the stigma of his dirtbag past. He doesn’t have to convince anyone that he is able to learn new things. No one will judge him at the latter end about his decisions in the former life.
    Hopefully it will all turn out okay and someday I can quit my job ceremoniously for round 2 of adventure.

  • Jay c

    I quit my job to live on the trail permanently three years ago. The planned trails have been beset with problems, but those problems simply presented other, new opportunities. Such as the insufferable heatwave in the Italian Apennines which made the 400km hike too risky… I abandoned it and spent two lovely unplanned months on city tours in Tuscanny – Rome, Florence, Sienna, Sansepulcro, Arezzo etc. and learnt so much about the Italian Rennaissance. Or the two month Pyrenees hike which I had to abandon after waking up in hospital, but the doctor treating me and I fell in love and we have since spent wonderful times/holidays together in Paris, Biarritz etc.

    I recently met a great, inspirational Swiss guy in the Pyrenees who not only quit his job to hike permanently, he actually GAVE AWAY all of his possessions AND his house!! A modern day Francis of Assisi? All he owns are the clothes he wears and what he carries in his sack. He’s had to quit his planned hike (he’s “only managed 4,500km so far”) due to joint problems, so is resting for six months at First Nation reserves in North America before continuing his epic hike to Jerusalem. He said (quoting Churchill) ” Plans are there to be changed. ” I guess what I’ve learnt is that yes,plans don’t always work out, but freedom offers new opportunities and experiences.

    Ive met so many people on the trail who’ve ‘taken the leap of faith’ to step off the tread mill. I wasn’t reckless about my decision, I have a contingency plan, have rented out my home successfully, and when consulting my accountant/financial advisor about the plan he said “Jay, you would be surprised at the amount of clients we have on our books who pack in a perfectly good job to live their dream, whether they want to buy a boat and sail around the world, cycle across Europe, climb mountains, whatever, you’re not alone.. Go for it!!”

    The guy that fuelled my plans was a guy who decided to become “Of no fixed abode” since losing his job, and he’s done some inspiring stuff.. He said (encouraging me to take that leap of faith) “In your circumstances, the only thing that can stop you is YOU. Don’t let emotive fear stop you”.

    Ive never been happier, and in my early forties, I can see myself living like this until I’m no longer physically capable. I’d say to anyone thinking of quitting their job for a new life, no matter what that new life may be, don’t be reckless or foolhardy, get financial advice, be prepared to change plans on the journey, and that there will always be stresses and problems in life no matter what. And good luck to those who conquer their emotive fear, make that leap of faith, and go for it!!

  • Seamus Murphy

    We love it, because secretly we want to do it, if we haven’t already. It’s that simple.

    As for the people commenting on people with safety nets, there are loads of people without who still do it. So stop bitching.

  • Steven

    I’ve done this a few times, and it has always been rewarding. If I could do it again, I would:

    1) Have bought a house when I first started working. For although my career has not suffered, I am priced out of the housing market in many cities now.
    2) Saved a lot more money when working, and put it securely away in a 401(k) or similar, as I’m a little behind on retirement savings now.
    3) Gone minimalist a few decades earlier, as all the stuff you buy just holds you back in life.

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