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


Carlos Saborío April 24, 2014 at 1:18 pm
David Cain April 24, 2014 at 1:22 pm

The “doing what you love devalues undesirable work” argument is a load of crap, as I explain here:

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Garrett April 25, 2014 at 11:15 pm

A person can strive to do work they love *and* be empathetic toward the underprivileged. Ideally, one’s work is enjoyable and constructive. Sadly, as anthropologist David Graeber points out, many jobs (like those in the financial sector) are “bull shit” jobs (see my response to Jordan Bates above). But I think there’d be less oppression and exploitation if more people could manage to follow the advice offered by Howard Thurman, who encouraged people to do what makes them “come alive.” And this would lead to more emphasis on what David Korten calls real wealth ( and less on what he calls phantom wealth (

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Garrett April 25, 2014 at 11:31 pm

I’ll just add that I can certainly agree that compensation is out of whack. The New Economics Foundation produced this brilliant article several years ago:

Having now read all of her article, Tokumitsu’s main gripe seems to be with the notion that enjoyable work isn’t work (she quotes someone from the Carlyle Group saying as much). And I get her point. But that in no way proves DWYL isn’t a worthy pursuit.

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Garrett April 25, 2014 at 11:41 pm

All that said, I dream of a return to a moneyless gift economy, which once dominated (contrary to the myth that humans bartered and then created money to simplify matters–read David Graeber’s book “Debt: The First 5000 Years”). Denying people essentials (that which has intrinsic value) on account of lacking a human construct with no intrinsic value (i.e., money) is one of life’s great absurdities and atrocities.

A gentle detractor April 29, 2014 at 4:33 am

Garett, I enjoyed reading Graeber’s article. I take his point.

However, don’t let’s get all huffy and judgemental about what jobs are bull shit. Are you so sure what you do isn’t one? What would happen if your tribe disappeared, eh? Children would stop becoming adolescents, or pubescents adults? Talk about horse shit jobs!

And only an ignoramus would imagine that if all private equity professionals disappeared there’d be no repercussions. Believe you me, we’d have a minor catastrophe!

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A gentle detractor April 29, 2014 at 4:48 am

I’m sorry, that came out sounding far more aggressive than I’d intended!

I don’t want to denigrate your specific profession, or Graeber’s. But I would discourage you from denigrating others’.

As sudden disappearance of corporate lawyers and PE professionals would affect us far more profoundly than extermination of anthropologists and counsellors to adolescents, as you’ll realize with a minute’s reflection.

Garrett April 30, 2014 at 12:11 am

There’s no denying that human societies (particularly those in “developed” regions of the world) have constructed jobs that have been made important. Likewise, there’s no denying that human societies have denied the importance of that which has intrinsic value. GDP is the dominant economic metric, but it’s more than flawed–it’s actually quite absurd ( That’s the point made by David Graeber, David Korten (who draws a distinction between real wealth and phantom wealth) and others.

A gentle detractor April 30, 2014 at 6:08 am

No, I’m not talking about money measures, not salaries, not GDP, but actual social worth, real usefulness. Take PE. PE plays a crucial role in owning and directing capital. If they disappeared tomorrow, the whole capitalist.system would shudder and totter. Likewise, corporate lawyers facilitate the work of, well, corporations. Let them disappear, and dishonored contracts and the like would deeply trouble us.

If these professions provide ‘indirect’ value, unlike say a farmer’s, might we not say the same of what you do, or what Graeber does?

(Just making a point, no offence intended. At a personal level what you do is great.)

Garrett April 30, 2014 at 6:36 pm

Again, the fact that various BS jobs and the very notion of what constitutes “capital” have been made important (i.e., their sudden disappearance would lead to temporary devastation) doesn’t make them inherently important. One can make an idol of something without it being worthy of idolization. To put it another way, what is and what should be (from a humane, compassionate point of view) are often at odds. And, yes, that’s an opinion. All any of us are sharing are opinions..

Garrett April 30, 2014 at 6:42 pm

What you seem to be referring to when you say “capital” is an example of phantom wealth. Phantom wealth dominates in our particular society, but should it? I don’t think so. Enslavement of fellow human beings once dominated, but we can all I agree (I hope) that it shouldn’t have. Again, what is and what should be are often at odds.

A gentle detractor May 1, 2014 at 4:09 am

Ok, I hear you. You’re basically the guy who, in an age of monarchy, is questioning the usefulness of the king. I agree with that, in purely idealistic terms, my own profession notwithstanding.
But what do you suggest, then? I don’t like oily politicians either, but they are necessary to democracy (the politicians, not the oiliness). Ditto capitalists in a capitaist society.

I agree neither is perfect, but democracy is the best political system we have, and capitalism the best economic system we have. Do you agree with that statement? (I agree there’s huge scope of improvement, but do you agree with that bare-bones statement?)

If you do, by definition, then, PE professionals and politicians become necessary and essential (the ecxact opposite of a BS job). And ditto corporate lawyers and the rule of law.

You just cannot do without these jobs in the present disposition. And what other disposition is there? (Or would you prefer a communist regime, or perhaps a return to the divine right of kings? Then we won’t need PE types — biut we’ll then need kings and KGB thugs!)

Garrett May 1, 2014 at 7:07 pm

First off, I’m not a proponent of any -ism. There is not, nor can there be, any large system that is purely this or that. As for communism, everyone regularly practices it on a small scale (e.g., a parent providing food for a child) if you use the following definition: from each according to her ability, to each according to her need.

I sympathize with left wing libertarianism (not to be confused with the right wing variety and free market BS espoused by the likes of Ron Paul), but I can’t subscribe to any -ism. And left wing libertarianism is not realistic at this time. To quote Noam Chomsky regarding the continued need for a federal government, “it’s completely realistic and rational to work within structures to which you are opposed, because by doing so you can help to move to a situation where then you can challenge those structures.”

Per Dunbar’s Number, our monkeyspheres are limited. So, I like Jeff Vail’s rhizome network idea that he expressed in a short book that you can read online if you like. It’s called A Theory of Power and you may wish to just read chapter 9. Or you can Google “Jeff Vail and rhizome” and find things like this: And this:

Democracy is only feasible on a very small scale. The U.S. as a whole is certainly not democratic, as Robert Jensen points out here:

But what to do, what to do. Well, live intentionally. Think globally and act locally–don’t just have a bumper sticker with that quote on it, but actually think globally and act locally to the best of your ability. That’s my advice and what I try to do–admittedly, I sometimes fail. Ultimately, I agree with Jiddu Krishnamurti, who said, “…if we would change society we must first change ourselves.” A friend said that he thinks empathy is the next rung on the social evolutionary ladder, and we – as a species – are clearly not there yet.

A gentle detractor May 12, 2014 at 12:12 am

Krishnamurti, eh? That’s the deep end of the pool, as opposed to the kiddies section we and this thread have been splasing around in!

I’ve read some JK, but cannot claim to fully understand him. But i do understand enough to realize his depth, to understand he’s no jargon spouting charlatan.

You raise interesting points. But, garett, arent we derailing our discussion, which was on what jobs are bs? :-)

but no problemo, after all our whole discussion was a derailment of the thread

anyway, nice talkin’ to you

ps sorry if this gets double posted, my last didnt show somehow so i retyped this

Mark April 25, 2014 at 8:57 pm

There seems to be a lot of discussion about loving the work we do. Someone raised the exact same question I once had – if we all do what we love to do, who will pick up the garbage or clean septic tanks? Before I continue, about me: I left my well paying federal government job 3 months ago because it was unfulfilling and I lived in a cubicle. Everything David has said along with other readers all resonates with me. I have taken things one step farther, and moved to paradise in Turks in Caicos. Back to the point…I recently took a personal development course by Darren Hardy titled “Insane Productivity”. In one of his teachings, he explains this issue we all have about doing what we love to do from his perspective, and it completely blew me away. The average person can actually love anything they do. There are 4 ways this can be: 1) loving the thing you actually do every day (how society traditionally make judgements) 2) loving HOW you do your work and taking great pride in the workmanship i.e. most house cleaners 3) if you’re working to support a person, a loved one, a friend 4) WHY you work the job you do. It doesn’t matter what you have to do, you’ll love it because the reason why makes you cry. The garbage truck man or septic tank cleaner can be applied to at least 3 of these 4 explanations of loving what they do. Does this help anyone else make sense of the argument? Love your writing, David. Keep explaining the world to us, and help us make sense of it all.

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Jacqueline Golightly May 7, 2014 at 7:12 am wrote exactly what I was thinking…I just couldn’t get it down! Thank you.

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Tobi April 25, 2014 at 11:32 pm

To me, it seems that most people who try to “find work that they love” will likely end up on the streets before that happens. Art and volunteering are great, but not if you want to eat. Or you have to dedicate the best years of your life to someone else just to grow a big enough mustache to save the downhill years for yourself, what a world.

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Duska Woods April 26, 2014 at 4:44 pm

Having been self employed realtor for many years I have hard time even imagining working 9 -5 job, but I can relate to what you are saying about breaking away for some kind of authority however illusory it is. I have to many interests, art, writing, design that self employment and flexible hours allow me to diversify. But, I do however have a great deal of respect for millions and millions of people who work at jobs to make the life for the rest of us comfortable. Some of those jobs are indispensable for the rest of us to have food, electricity, fuel, healthcare etc. Those 9 -5 workers are the invisible brave men and women who get up every day and go to their jobs weather they like it or not so that they can feed their families, send their children to school etc. I often think of this when I make these statement of not being able to imagine working 9 -5 job, because the truth is, if I had to I probably would. I am sure that the transition from the 9 -5 job to independent self employment is a big step in ones life and I congratulate everyone who gather enough courage to make that transition…

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Andy April 26, 2014 at 5:51 pm

Having made the jump myself in 2009, i can say without doubt that you won’t regret your decision. I still remember visiting my first client as a freelance web designer, and laughing to myself on the way home at finally doing something that i actually wanted to do. I agree with you wholeheartedly that out culture trains us for a life of yielding to authority, from parents to teachers to employers. The problem i face now as a parent myself is how to prevent my daughter from being brought up with the same ‘yes sir’ attitude that i was. Any advice from other parents would be greatly appreciated :-)

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A gentle detractor April 29, 2014 at 1:29 pm

Careful what you ask for! There’s a reason governments generally hate anarchic freethinkers. And freethinking children can be 10x worse than the worst anarchists, as you may yet discover for yourself!
(all right, kidding!)

On a serious note, you can try corporal punishment every time she dared to agree with you.

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Koobazaur April 27, 2014 at 2:02 pm


Awesome post that resonates with me; I’ve been working as a self-employed freelancer ever since I graduated (and even during my studies), which was almost 3 years ago. Even today I still have many days when I wake up and stare at my ceiling wondering “what am I going to do with my day…?”

One thing I wanted to add – overwork (and associated anxiety) can be just as bad as under-working. Back when I was in midst of releasing my first indie game, I worked like crazy (12hr days were uncommon). The fact it was my “baby project” just made it worse, because I didnt want to stop, even tho I could feel my brain burning out and needing a break. If you are curious, here’s a system I kind of settled on that helped me out: .

Still, I find it sometimes challenging to balance work vs. free time, and often feel I haven’t “earned” the relaxation time if I haven’t worked x-amount of hours. A leftover from school, a short 9-5 gig I did and general societal expectations, as you point out yourself.

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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!

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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:)

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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.

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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.

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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…

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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. :-)

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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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Lien June 1, 2014 at 1:12 pm

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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.

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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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