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The frightening thing you learn when you quit the 9 to 5

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As most of you know I quit my day job last fall to transition to making a living through my writing.

When I was preparing to give my notice, I met a UK-born writer named Robert Wringham, who publishes an independent magazine for workforce escapees such as myself (or those who are thinking about it), called New Escapologist.

I loved it immediately: it’s smart, advertising-free and perfectly square. Given that I was in the “great escape” chapter of my own story, he asked me to write a piece for the magazine, which appears in the latest issue. I’ve reposted it below (edited slightly to fit a blog format.)

The months following my escape consisted of one lesson after another, as I expected, but the biggest lesson was quite a shock — and it’s something all 9-to-5ers should learn as early in their lives as possible. This piece is my warning to would-be escapees who are eternally waiting for the right time.


After leaving a jobsite, I drove to a nearby field and parked my car facing a row of corn. It was afternoon, on the day that I’d picked to finally do it, but I was still nervous. I sat there for about half an hour before pulling the trigger.

I phoned my boss and told him I was leaving the company to work for myself. I’d rehearsed for a confrontation, but he was very professional and understanding. The moment I hung up, laughter exploded out of me, like I’d just gotten a joke told to me years ago.

The drive home was euphoric, as I expected it would be. But two weeks later I would discover an unsettling side-effect of having been an employee so long. 

I enjoyed the weekend after my final office Friday as normal. However, the following Monday happened to be a holiday, which I quickly realized carries absolutely no benefit to the self-employed man. My former colleagues were getting paid to do anything but work, while for me it was simply another day. If I chose not to work, it was my loss and only mine. When you’re self-employed, every day is Wednesday.

This feeling of absolute responsibility for the outcome of my working life was a new feeling. It dawned on me that before I quit my job at 32, I had never really experienced a self-directed period of my life in which I was actually trying to accomplish something. At 29 I went backpacking for nine months just to see what it’s like to be me in other countries. It was an unforgettable experience but it didn’t involve any goals or specific intentions.

Aside from that rewarding but relatively aimless period, I was always either a full-time employee, a student, or a dependent child. This meant I’d always had a) someone telling me what I ought to be doing, and b) a network of reminders, best practices and potential punishments that together almost guarantee a certain acceptable range of outcomes. The worst that could happen is that I’d gradually advance along the current ladder, as long as I did a reasonable job at coloring within the lines provided.

I didn’t realize it until the lines were no longer there, but this type of subservient arrangement trains a person to need others for direction. When I woke up that first Monday, free for the first time to build a life on my own terms, I began to realize that I have exactly zero experience doing that.

Few of us do, because we’re born as subjects to the authoritarian figures of our parents, and from there we’re funneled straight into the education system, which steers us directly toward the employee workforce. In each of these systems, we are subordinates whose work is likely to be unrelated to our own values, on schedules that are always determined by someone else.

We’re trained to need bosses

It seems inevitable, then — though completely insane — that for the first 33 years of my life I was never the one determining the basic day-to-day structure of my life. When you only take full control of your life less than a decade from middle age, it’s alarming to find yourself allowed to actually put your hands on the wheel. There’s a conspicuous absence of instruction, and it feels strangely like you’ve done something bad.

Thirty years of conditioning is extraordinarily difficult to overcome. Most people, when they emerge from the conventional child-school-workforce tunnel, are almost entirely untrained to manage entire weeks and months in which the bulk of one’s time isn’t committed to serving an institution of some kind.

Given all my life experience, subservience is the quality in which I’m most highly trained, and I suspect I’m a pretty typical case. A friend of mine is a blogger turned New York Times-bestselling author, and he told me much of the reason he hasn’t left his corporate job is because he’s aware that without the structure imposed by a job, he’s liable to devolve into an unwashed caveman, eating cold cereal three times a day and gradually forgetting how to talk.

His fears aren’t unfounded, in my experience. I notice I shave less often, my hair has grown long enough to cover my face, and my lunch is often just apples and raw almonds. There are days I don’t go outside. It’s been three months since I sat and laughed in the cornfield, and I am only now beginning to adhere to a day-to-day workflow structure of my own design. Each day is a blank page with no outline indicating where the crayons go. I have to decide what to draw, how ambitious or humble it’s going to be, and what it’s all going to add up to over time.

This is exactly why we all ought to be thinking of our escape from kindergarten on. I wish somebody had pulled me aside and told me that the education system and working culture I’m going to be marched into are places that are ultimately going to need escaping from, because otherwise I’d never quite get a chance to run my life. These institutions may be useful for learning the fundamentals of language and human interaction, but they’re generally inhospitable for the finding and doing of the work that’s most important to you.

The giant brick sitting in your salad

I’m convinced now that nobody gets away with settling on work they don’t care about. The nagging banality of having to do irrelevant work five-sevenths of your days is not something that will eventually leave you alone. Nobody ever makes peace with with the ringing of their alarm clock. We either make a calculated escape, or resign to becoming cynical, bored — and worst — dependent on constant entertainment for relief, because our work does little but drain us.

Independence has to be practiced throughout life beginning as early as possible, because by the time we recognize the need to escape, we’re extremely dependent on the day-to-day controls provided by school and work culture. This makes change a steeper proposition with every year that goes by.

Among other depersonalizing habits, resignation is perpetually being trained into us until we do finally make our escape from institutional life. At the beginning of your life, you must resign to what your parents allow you to do. Then you must resign to the tedium of twelve-plus years of public schooling, and from there you naturally believe you must resign to the banality and irrelevance of whatever work is required for you get the next paycheck.

Many people deal with the vapidity of their jobs by having children, because parenting lends an immediate seriousness and purpose to one’s role on the planet. Providing for a child is an act that feels intrinsically meaningful to a human being, and so devotion to your job, even a dull one, can become an extension of devotion to your role as a parent, giving meaning to the hoops to be jumped through at work.

But not everyone wants their primary contribution to the world to be in the field of parenting, and even for those who do, the job still feels like a necessarily evil done only to make this passion viable. Unless you love your work, your workday probably feels something like a giant brick sitting in your salad, and in my experience this doesn’t go away until you do.

Much better than resignation is to make a long-term plan to find work that is valuable enough to you that your typical day is a fulfilling one, and valuable enough to others that people will pay you for doing it.

I dream of a future in which this is the norm — where everyone expects to spend as long as it takes to find fulfilling work. The resignation rate for us, presently, seems extremely high. Imagine the difference, not just if you found your own work fulfilling, but if almost everyone else did too. Products would be better and we’d buy fewer of them. And the people selling them to us would be proud instead of indifferent, because their work and their joy would no longer be confined to different parts of the day.


If you have escape on the brain, you would probably really like New Escapologist. It’s full of escape stories and practical advice on how to become a fellow fugitive. You can check out the blog here

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Nicole April 28, 2014 at 4:53 am

Wow! Amazingly articulate, powerful, and moving! You are a brilliant writer and I literally laughed out loud at the caveman comment. As a fellow escapist going on her 6th month free from the clutches of corporate America, your words fully resonate with me! Bravo, sending this to people who need the motivation!

Beatrice Marta April 28, 2014 at 3:16 pm

Wonderful thoughts! THANK YOU!

It’s been 4 years since I’ve embarked on this journey; BEST decision I’ve made so far cause it has taken me through some very exciting experiences. I’ve learn some amazing things along the way and I’m definitely sticking around to see what’s next.

Must admit, even when I was employed in the same field I am still working at the moment( interior design), I felt I could do so much more if I wasn’t part of that type of a hierarchy. Somehow, I never resonated with that convention, which is why my parents don’t understand the reasons I can’t have a “normal” job like everybody else.

There is something so empowering and super scary at the same time about being totally responsible for yourself. Sure, not knowing when/how the next bill or meal will be paid for can be quite intimidating but it is in those moments one can find enormous and unimaginable sources to move forward and become stronger, wiser, more aware and creative … you name it.
I think this kind of a choice is one of the best ways to evolve.

I’ve never enjoyed designing as much as I do now, who knows if that is what I will be doing for the rest of my life, perhaps this is not even important; the things I know for sure are the criterias I decided to live my life by and spending my precious time on the things I love while being of service are on the top of the list.

So, for those of you have quit the 9 to 5 : WELCOME ABOARD!
and those who are thinking of it : TRUST YOURSELF & DON’T WORRY + YOU’RE NOT ALONE, WE’RE HERE:)

Sophia April 29, 2014 at 1:51 am

As long as one has to earn money by working, one always works for others in some way, as one depends on others to buy one’s products and services.

The mode of working for others may change, but not the fact that one works for them, depends on them.

jamie flexman May 1, 2014 at 2:10 am

It is a strange feeling to severe the ties from your 9-5 and suddenly feel like you’re adrift in the big wide world. I quit my job almost 2 years go and I remember that final week (I had to give notice) as being totally stress free. It was liberating.

I didn’t really know what I was going to do but I had a feeling it would be guitar related – and so it turned out. I’m now a guitar tutor and for the first time, my own boss. It’s weird, but I couldn’t ever go back to that world again. Not that I’ve tasted what it’s like to go solo.

But you’re right, the weirdest part is definitely not having anyone to answer to or to tell you what to do. Learning discipline took a while, but I think I finally managed it.

Genevieve Hawkins May 3, 2014 at 9:57 am

Love this. I’ve been self employed for so long I no longer understand the concept of a “real job.” Every day is Wednesday, indeed. My “work” schedule is usually determined by my 14 month old child’s sleeping patterns. I might be working at 4 AM on a Saturday. I might take three days off in the middle of the week. In the slow season, I might take a month off.
The deeper question is what is considered valid “work?” Is taking care of your child valid work? Or tending a garden? Or writing a blog? Seems to me that the very rich and the very poor don’t work.
Here in Thailand food grows out of the ground, fish swim in the sea, chickens and ducks run in the road. The temperature never drops below 70 degrees F. So working for food (or even shelter, which can easily be built) is not necessary. So many reports focus on how the average person in a third world country lives off (whatever tiny amount, say $2 US) per day…they don’t mention that basics may be covered already.
I’m not sure if many people in first world countries would know what to do if groceries stopped being delivered to their local store, if water stopped coming out of the tap, or if the electrical grid just shut down…
It takes a while…take a deep breath…life is change…

Jacqueline Golightly May 7, 2014 at 5:18 am

Hello David,

I am a 45 year old good girl gone bad. As your article says, we are programmed from birth to commit to complying. In the West this means acquiring things we don’t need with money we don’t have in order to keep society moving via “being good for the economy”.
I pleased my parents with excellent academic grades. I joined the civil service at 18 years old and combined trying to make sense of counting widgets for the government with raising a family including a very disabled son.
I got out a month ago. I have no such Stockholm syndrome to my employer of the last 27 years. I feel like I climbed out of a window and I’m now running for the hills. It’s exhilarating and I feel more alive and in love with life than I have ever done.
I find your observation that it is hard to acclimatise to being captain of your own ship very interesting. I suppose I would add that working is not the only responsibility we have in life and maybe those lucky enough to be free from caring commitments or financial hardship may find creating a routine difficult once performance targets and punishment through pay are removed as carrot and stick to our existence.
I have a considerable burden due to my son’s severe autism. However, I am also very fortunate in having done as others on here have suggested and I planned for an uncertain future at the start of my career and therefore I have security enough not to have to replace paid employment with self employment. I am free from the whole hamster wheel of doing things to have things equation.
I have not been highly paid..I’ve just had little interest in tat. I have always bought good quality food and being warm, dry and occupied have been my goals for my now grown up family.
I see a direct link between removing the addiction to consumerism and being truly free from doing things we don’t want to do. If productivity is still important to leavers ( and if we’re being truly radical, does it matter) then maybe a way of measuring life well lived is in how we spend our days not how we can spend our money.
There is no amount of money that can “produce” or “purchase” what I will have done today. I made breakfast for my husband, I put washing on the line, I took my father to hospital and I read your thought provoking post. I’ll make a casserole and then watch a good film on my own this afternoon from a hundred i have recorded for free on TIVO. I’ll feed my husband son and grandson tonight. I’ll chat to my husband and visit my father with a newspaper and flask of soup. I’ll have a warm bath with my meditation music ( I like tibetan rain from Youtube) then I’ll watch a drama and news with my husband before bed. I’m not stressed, I have the housework done, I’ve cared for my family and myself and I get to ponder things like a good storyline or a lyric that resonates.
I’d say…work hard, spend less, get out quick and live long and prosper on the things that matter!
Thanks for making my days even more enjoyable. :-)

ANDREW C May 18, 2014 at 4:17 pm

hey thanks a lot for the article, i don´t know how I got here, but it let me assert that quit my job was the best decision i have ever made, congratulations on your article, through your words generate many feelings.
greetings from Ecuador

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R July 14, 2014 at 4:12 pm


I’m on the verge of giving my notice in i.e this week, from a fairly comfortable job with all the perks. I do enjoy alot of my job, but i feel if i’m doing this for the rest of my life, i will only look back in regret. I want to pursue my dreams. However, the more i think about how my life will be outside my organization, where i have made friends and there is a community, the more i become fearful. Another thing that i’m starting to fear and also feel is loneliness, away from the flow of he big city commute and then talking to work colleagues. Not sure if i can do this. I’ll let you know how it goes.

Jean August 8, 2014 at 2:58 pm

“This feeling of absolute responsibility for the outcome of my working life was a new feeling. It dawned on me that before I quit my job at 32, I had never really experienced a self-directed period of my life in which I was actually trying to accomplish something. ” This is really sad.

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