Switch to mobile version

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

Post image for The frightening thing you learn when you quit the 9 to 5

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

BNL April 20, 2014 at 11:35 pm

David –
I agree with almost everything you said, although my opinion is not yet from experience considering I won’t have that first unpaid day for another 10 days.

The one challenge I have with this post is that when you talk about finding “work that you love” that it still implies some inherent human dependence on “work.” Sure, losing the boss for the first time (parent, teach, boss progression) is a great step to getting out of that mold, but why must “work” be part of the next stage? Jobs are relatively new when you consider the entirety of human existence. Or are you even referring to a literal job when you refer to work?

This is just something I think about a lot, as I approach my own looming retirement from my 9-5. I’d be curious of your thoughts, particularly since you are several months into your escape.

David Cain April 21, 2014 at 8:46 am

Well, paying the bills must always be a part of the next stage, and for non-financially-independent quitters some kind of work will be necessary. But when I’m talking about “work” I really mean it as something to do, to produce, to contribute. It could be art, or study, or volunteer work.

Alasdair Shepherd April 29, 2014 at 9:08 am

I’d argue that “work” has always existed. The “jobs” we’re all familiar with in this post-Ford world – the 9 to 5 with time off to go buy all the shiny things we’re making for each other – maybe not, but to work is to have a function in society.
We’re an inherently social creature – have been since long before the advent of this whole sentience kick we’re currently on – and even back in our hunter-gatherer days you were either a Hunter or a Gatherer. Or the tribe’s shaman, but even they served a purpose, whether you and I think it spurious or not.
And that extends up to the present day; even purveyors of pointless tat / filth / anything else a particular person might not approve of serve a function to someone.
If you quit your job and then do nothing for the rest of your life – which in my mind means vegging on the couch for forty years before kicking the bucket – you’ll probably go mad. I really do think there is “some inherent human dependence on ‘work’.” As David said, though, that just as readily describes art, study or volunteer work as it does having a job.
Even the big names in the Internet Early Retirement movement – Jacob from ERE, Mr Money Mustache, J.D. Roth of Get Rich Slowly, so many others – still “work”. They just do it for a purpose or a passion rather than a pay-cheque.

Astride Costa May 20, 2014 at 8:01 pm

If your doing something you love, its less of a work and more of a dream. Thats why it would take the time it takes for you to find this sense of work within your passion that creates the upmost freedom and financial stability.

Aditya Thakur April 20, 2014 at 11:46 pm

I too quit my job 2 years ago. But unlike you and most other people I did it without any plan in my mind. I worked as a sailor and after signing off from a ship I wasted a few months drifting around and then just decided not to go back. So I never had the cornfield moment because I was already working on contractual basis. I guess subconsciously I knew that if I quit sailing I’d pursue my passion of writing by becoming a freelance writer.

When I quit, I too realized this fact; the best thing about freelancing is that you are your own boss and the worst thing about freelancing is that you are your own boss. For the first year I struggled just to get my employee to show up at work. Going bankrupt helped.

I agree with everything you are saying. But recently I came across a thought which I haven’t been able to answer. Maybe you can help me.

If everybody does what they love then who’ll pick up the garbage? Surely there’s no one whose passion it would be to pick up the garbage or clean toilets? Can everyone in the whole world one day do what they love? Or is this only for the privileged rich and middle classes?

David Cain April 21, 2014 at 8:54 am

>If everybody does what they love then who’ll pick up the garbage? Surely there’s no one whose passion it would be to pick up the garbage or clean toilets?

No, not everybody can do what they love. I don’t see that as a reason to avoid doing it if you can. Not everyone can be healthy either, nor can everyone can be happy, but being unhealthy or unhappy simply for that reason would be pretty ridiculous, wouldn’t it?

It is helpful to be aware of your privilege (and privilege isn’t entirely a matter of economics — the greatest privilege is to be able bodied with no serious mental illness) but I don’t understand why some people associate guilt with privilege. Most people who have privilege let it go to waste, and there’s nothing honorable or compassionate about that.

mariavlong April 22, 2014 at 9:56 am

The garbage “obstacle” is pretty bogus in my opinion. If everybody was more judicious about their waste and about what they consume, there would be very few truly crappy tasks because of individual responsibility to creating a healthy non-addicted to excess community.

Michelle Coughlin April 22, 2014 at 3:17 pm

The couple who cleans my home work for themselves. They support their 3 children on the income they make from their cleaning company. They do find great pleasure in their company, the freedom to choose their clients, to work when they choose, etc. They are very happy people who are passionate about their work and do a good job. Why shouldn’t people love to clean? Or to pick up trash…is it so different than delivering mail? I find this train of thought difficult to comprehend. Many people in the service industry love their work. Must a task be intellectual in order to be loved? Can’t a physical pursuit be satisfying and enjoyable?

Zoe L April 21, 2014 at 9:14 am

hey there, I’ve had that same thought about the garbage.. I wonder to what extent exercising privilege in this area (finding a way to do what you love for work, in a self-aware/purposeful way) is related to others not being able to exercise theirs, if at all. What do you think? I wonder if it’s not a bit naive to assume that it’s a win-win scenario..

Aditya Thakur April 21, 2014 at 10:31 am

I speak from the side of do-what-you-love but I have to say, this thought has bothered me a lot.

Let’s say that those who can should do what they love. That means at least some (or most) will still have to do what they don’t love. We can try to not feel guilty about it. We can say, hey I can so I did.

But I think the question of doing what you love only arises when you are at a certain level. You live in a society where you have decent facilities and security and health safety and know you won’t starve to death. You have enough educational qualifications to do something if worse comes to worst. But if you are born in say Africa you have to worry about health and war and day to day food and clean drinking water. Then you take whatever job you can get. You never think about doing what you love. Or maybe you are lucky enough to find some time to do it on the side.

I think the real answer is that everybody can’t do what they love. If you can then you must because it’s really a big privilege to have in this world. You are really lucky and yes you shouldn’t have to feel guilty about it.

Everybody can’t do what they love so if you can, then you must.

Garrett April 23, 2014 at 10:13 pm

Howard Thurman said, “Don’t ask yourself what the world needs. Ask yourself what makes you come alive and then go do that. Because what the world needs is people who have come alive.”

I like to think that if more people followed Thurman’s advice, fewer people would essentially be forced to do work they despise. That would slowly but surely diminish exploitation and hopefully place more emphasis on real wealth instead of what David Korten calls “phantom wealth”: http://livingeconomiesforum.org/phantom-wealth

Derek April 21, 2014 at 12:35 am

I quit my life of employed servitude in 1996. I had had enough of watching people with a supposed senior ‘rank’ to me (they were paid more for their time) display their incompetence, greed, lack of care day in day out. There were so many of them in the large shipyard where I worked they drowned out the few ‘good guys’ so I hatched a plan to take redundancy and open a bonsai nursery in the small town where I lived.
Planning everything except where the customers were coming from (hindsight) I leapt to freedom in Nov 1996… except it turned out to be a leap into employing myself. As employer and employee I had the worst of both worlds.
I had had 18 years being employed and then I employed myself for a further 14 years. In 2010 after my mother died I quit again.
This time I had no plan I just quit but this time I felt it was the right thing to do. Hindsight shows me that the 1996 quitting was simply a way of getting out of ‘tick tock’ (the time for money exchange which is designed to strangle human creativity).

It’s taken me almost four more years of quite literally doing nothing to come to accept that my feelings are better placed to guide me through life than my mind is. My mind hoovers up enormous amounts of information, stores it and then forgets where it puts it all so it lives in a frantic motion of past thinking and future thinking seemingly unaware of the fact I and it actually live in the moment. My feelings simply appear and make suggestions which are appear to be physical and mental and at the same time appear to be in another place.

Now my direction is to make a life upon the land. The first intention is to feed my family and provide them with water, power, warmth, shelter and enough money for daily needs whilst giving them the opportunity to be as creative as they wish and find their own paths to happiness. Once that has been set in motion the next intention is creating so much abundance it has to be shared with as many other people as possible. Once that is under way then I can practice at becoming nothing. (with a thank you to Stuart Wilde for that insight).
I have no intention of retiring or quitting again. It has taken me fifty three years to figure this out but hey we are all on our won paths and we are right where we need to be at every moment of it.

A Longish ramble but thanks for allowing me to share, big love.

David Cain April 21, 2014 at 8:57 am

Good for you for making these bold moves. Most people just think about it.

Matthew Anderson April 21, 2014 at 1:20 am

I love this article so hard…

You’ve managed to put words to a sensation I experienced for the entire first year of working for myself. For a while I felt aimless, even though I had a very deliberate plan when leaving my old career. It was hard to put a finger on, and even harder to explain to others.

Ultimate freedom was terrifying at first, and I found myself paralyzed. Eventually I started to grow accustomed to designing my life, and it has continued to get better every day since I emancipated myself.

I’ve been writing about my experience leaving my old career behind as well. It’s something I urge nearly everyone to consider, but I think it should be considered very carefully. Without a very deliberate plan, things could quickly disintegrate into chaos for some people.

Thanks for the article, David! I’m looking forward to checking out New Escapologist.

David Cain April 21, 2014 at 9:02 am

Even if it doesn’t go according to plan, you learn a hell of a lot about yourself. I am still learning all the little skills it takes to be self-employed… the endless decision-making and second-guessing. I have grown more in this past few months than any other few months.

Matthew Anderson April 22, 2014 at 9:09 am

You will absolutely learn a ton about yourself! I guess I was just coming from a standpoint of thinking that it’s important to have a good plan in case you can’t earn any income for a while.

I’d hope that most people have a buffer saved up before they leap, and that they’ve tried to make some income in their new venture before diving head first into it, but it can be easy to get swept up in the romantic view of things.

Either way, the challenge has tested my limits and broadened my horizons much more so than any other experience in my life.

Odi April 21, 2014 at 1:57 am

I submitted my notice about a month ago without any plan. I may decide to work for myself but I’m not sure yet. The day I submitted my notice, I thought I was gonna have the cornfield experience but instead I got depressed for weeks. And I’m deeply wishing that I’d have a boss that would give me directions. Anyway, thank you for sharing your experience. This is interesting…

David Cain April 21, 2014 at 9:04 am

It’s hard to predict what will happen in big life moments. Take some time, it’s worth it.

Anne April 21, 2014 at 2:28 am

Thanks David – love the article. I retired 3 years ago, very suddenly: having resigned myself to having to continue working for several more years, at 57 I was offered a voluntary redundancy package and within 7 weeks was free. It’s taken me till the past few months to really begin to work out how best to manage my time, to balance routine and self-discipline with freedom and spontaneity in such a way that I live in reasonably clean and orderly surroundings (because that affects my mood profoundly) and have good food to eat, but also have space to write, create, read, reflect, socialise, relax. I’ve recently started a blog reflecting on the continuing process. I’d always expected to have lots of notice of my retirement and time to prepare, and the abrupt transition was a shock, but in fact I don’t think anything does really prepare you for the sudden and total change that you describe, from a life dictated by organisations and other people to the freedom (and responsibility) to shape your life and time for yourself. It’s not the same for a retiree, of course, because the pressure to earn isn’t there, but that responsibility for shaping a worthwhile and fulfilling life can still feel quite heavy as well as exciting and exhilarating.

David Cain April 21, 2014 at 9:07 am

Yes. It wasn’t so much the responsibility to earn that shocked me (although that does have its own weight) as much as this weird existential feeling of having your life finally freed for your own use, and not knowing how to do it. I felt like I had never been given so much responsibility before.

Albathin April 21, 2014 at 2:32 am

David – i’ve been a big fan for a few times now. This post struck a chord even though i’m no stranger to your message. You’re really spot on regarding the subject of children. I see it almost daily in the lives of my friends who are married and have children of their own. Keep up the great writing.

David Cain April 21, 2014 at 9:07 am

Thanks Albathin.

Andrew April 21, 2014 at 2:44 am

David, thanks again for posting another article – reading your posts on Mondays (here in New Zealand – you should come back sometime!) is one of the highlights of my week. Keep up the great work :)

David Cain April 21, 2014 at 9:08 am

I would love to come back!

DiscoveredJoys April 21, 2014 at 3:13 am

Like Anne I took early retirement (even younger). I had no need to earn money because the business I worked for had repeatedly offered voluntary redundancy over the years and I had saved and prepared for the opportunity, should it present itself…

I rapidly realised that I never wanted to work *for* anyone else ever again. Even so it took a couple of years for the new freedom to sink in. One realisation was that as a non-worker, a non-contributor, you lose ‘status’ in the eyes of those still working. You have to shake yourself free of ‘their’ expectations. That can be more difficult than you might think… we are social animals and we can’t avoid the chatter of the ‘troop’, or the lowing of the ‘herd’, or whatever collective noun appeals.

There is a huge temptation to do something socially recognised as ‘creative’ just to avoid having to bear the collective disapproval of doing nothing socially useful. It’s easier to say that you are ‘retired’ as most people understand that. They envy your freedom even though they disapprove of your non-contribution.

Ignore them, the herd is big enough already.

David Cain April 21, 2014 at 9:09 am

It is a shame that many people think the only contribution you can make to society is a financial one. I hope you don’t let them get to you.

Jacqueline Golightly May 7, 2014 at 5:42 am

Brilliant Anne…I’m fielding the “what are you going to do all day?” jibes and was tempted to describe the things I do to care for my son as an almost excuse for leaving my career.

“What do you do?” is the question that comes straight after “What is your name?”.

I agree that saying retired provides some diplomatic immunity to the negative feedback of saying “I do whatever I want to do when opportunity and time allows”.

My husband is hunter and I am gatherer. For the last 27 years I was wife, mother, civil servant. I’m now housewife, grandmother and carer but people still focus their opinion of my persona on the fact that I no longer tackle meaningless targets for the Insolvency Service.

My plan is to stay amused at the idiocy of it all. :-)

Jacqueline Golightly May 7, 2014 at 5:44 am

Sorry, I meant to direct my message to DiscoveredJoys regarding Anne’s experience.

I’ll get better…I promise.

Vilx- April 21, 2014 at 3:22 am

There’s one thing with all this “working for yourself, not someone else” movement that I haven’t been able to properly comprehend. Maybe you can help?

The idea comes from my current line of work – software development. When you work in software development you soon realize one important thing – software is fucking complicated. It takes a LOT of time to get it done. Even a tiny tool like Windows Calculator would probably take a single person a whole year to properly write and debug.

Which is why any serious software development happens within TEAMS. The larger the software, the more people you need on the team to be able to complete it in any reasonable timeframe. A single person can only do so much work.

And this is the same with a lot of things – movie making, construction work, running a hotel, car manufacture, etc.

So how does this fit in with the “do what you love, work for yourself” movement? If your passion lies in a solitary profession like writing – well, great. But what about the work that requires teams? If everyone on the team was striving to achieve independence… how would that work?

Every team needs a leader, so for all the members of it, they will invariably have to work “beneath” someone. And how would finances be divided? A project usually has just one stream of income, which has to be divided among the team members. So there will have to be one person who actually gets the money and then divides it.

To me, this sounds a lot like what a company is. Where’s the difference?

David Cain April 21, 2014 at 9:11 am

“Do work you love” and “Work for yourself” are not necessarily the same piece of advice. You can do work you love for someone else, and you can do work you don’t like without a boss.

I think it would be great to do work you love with a team. I would like to do that someday.

Vilx- April 21, 2014 at 9:30 am

True. Still these two things are almost always intertwined when somebody writes about them. I’ve never seen an article that would separate them. It’s like some kind of unwritten rule – “if you want to do what you love and achieve financial independence, you need to quit your job and go solo! It’s nearly impossible to do it while being In The System; while working for The Man! Self-employment is the right and only way!”. I guess that’s why I got confused.

Hmm… shouldn’t it really be the other way round? That most occupations would be better done in teams? Financial Independence and Doing What You Love are both good goals that people should try to achieve, but they don’t automatically mean that you need to quit your job, right – in fact, both might be better and easier achieved WHILE working at a company, no? You just need to find the right company.

Aditya Thakur April 21, 2014 at 10:35 am

Maybe in such jobs where many people are required, doing-what-you-love/work-for-yourself means to start your own company and be the boss and have a team below you that works for you?

Vilx- April 21, 2014 at 12:32 pm

Well, running a company takes a whole different set of skills than just doing one of the jobs at the company.

Jacqueline Golightly May 7, 2014 at 5:54 am

Hi Vilx,

I’ve had experience of working solo to pursue a goal of acquiring social care for my son. It’s a lonely business and requires real conviction not to give up.

I’ve also tackled similar issues as part of a team too. This provided a less isolating campaign but control of the outcome was devolved to the point of less satisfaction for a control freak like me.

I suppose it’s not only about leaving an establishment or working alone or even whether particular occupations benefit from group or solo contributions. Personality and preference will play a part in how effective we all are at achieving anything.
My sister can’t do the ironing without music blaring and surrounds herself with facebook twitter and real friends.
I like peace and quiet and a hanful of deep relationships. Working for a big organisation or setting up as a one man band may help or hinder our emotional requirements and therefore you’re right in saying neither scenario is perfect for all.

Lara May 13, 2014 at 6:33 am


I consider myself fortunate to do work I love, which happens to be in a pretty big non-profit.
Same with my brother, who is also in software development. He loves working on the big projects that bigger companies get that require teams, and he wants to be on the ground creating the software, so being self employed would take him away from what he loves. As Vilx said, management skills are a different type of work.

Not to say that neither of us would ever become self-employed (I wouldn’t be surprised if that’s where I end up), just that currently the work we love doesn’t fit in a self-employed model.

I really like this article – regardless of whether you’re in work you love / despise, employed / self employed – learning to create your own structures in life is one of the most freeing things you can do (I’m still struggling!)

Mars April 21, 2014 at 4:47 am

Very interesting perspective from an escapee! I wondered throughout how I would weather the freedom…

I’ve had self-motivation to pursue a few interests, one of them personal finance, for which I could read books, research and write about for hours.

But when my husband and I took a few months off between jobs, we ended up sleeping until 10am, lounging around in PJs until 12, having breakfast for lunch etc. I would spend most of the day browsing articles on the Internet, playing some games/watching movies, and maybe going out every now and then for coffee/shopping.

Since it was a short term thing, it wasn’t too much of a waste to destress from work burn-out, but I don’t think I could have continued long term. It was a relief to get back to work, to actually doing something constructive each day.

So balancing the two experiences, I’d say I’m going to struggle after I leave…. until I learn how to be independent.

+1 to Vilx’s comment above – as a software developer myself, I hear you!

Also, would it be possible for everyone to find fulfilling work, even if they remained employed under a company/team of individuals?

Surely there will be some significant number of individuals left doing the cleaning, managing, stock-taking, McDonald selling, whatever miserable or just plain boring job you can think of?

David Cain April 21, 2014 at 9:14 am

I get really depressed if I sleep in and don’t accomplish anything during the day, so that helps to keep me in line. I guess whatever your daily routine is, you learn what makes you happy and make the necessary refinements.

No it’s not possible for everyone to find fulfilling work. All the more reason to do it if you can. See my reply to Aditya’s comment above.

Chris @ Flipping A Dollar April 21, 2014 at 5:03 am

“Unless you love your work, your workday probably feels something like a giant brick sitting in your salad.” Well shit. This hits me hard in the stomach. You described my every day of work with one simile.

David Cain April 21, 2014 at 9:15 am


Miroslav April 21, 2014 at 5:25 am

Prtty much what I got a glance of the last few moths. I finished my Bc., couldn’t find a job for 6 months, and got to a point where I’d rather eat a live tarantula than painstakingly carve out just one more cover letter. Now I’m studying for admission exam for a Master’s program in computer science. Don’t know what that will change, but I guess it’s better than some survival shit job. During both the job search and studying, I wasted incredible amounts of time, because there were no deadlines to meet and nobody to give out assignments.

It stemmed from my previous way of life, of coure. I used to question the school a lot, and always wanted to do something more engaging. I wasn’t a Harvard Ph.D at 8 or anything, but I remember figuring out division on my own, asking the teacher for more examples of a math excercise I found interesting, and noticing that you can have even and odd numbers. But the grudging worksheets, curriculum set in stone that I had to chew through no matter how well or poorly I did, and parents who acted as if how well I managed to solve 40 boring addition problems without a calculator or write a letter 60 times in a row was the most important thing in the world clobbered all initiative or interest right out of me. By the 3rd grade, I accepted that my life means halfassing or cheating through the assignments they give out in school and receiving food and computer in return.

David Cain April 21, 2014 at 9:18 am

I noticed a huge difference in how I perceive time. When I didn’t have much discretionary time, and hour felt a lot longer. Now I often presume I need at least a half-day to get anything significant done, which isn’t true but it still feels like it.

Erin April 21, 2014 at 7:12 am

“Man is born free, and everywhere he is in chains.” Rousseau

I have not quit my job because I have children and I think you are correct that some of us try to find meaning by raising a family. I am trying to work up the courage to let go of my job and my pension and have faith that we will be OK.

I’m not sure all children a subordinate to their parents, it depends on the way the parents are parenting really.

Do you ever think about privilege when writing posts like this? I think there are only certain people of privilege who can even contemplate this as for many, it’s a struggle just to stay alive, even here in Canada.

David Cain April 21, 2014 at 9:20 am

On the topic of privilege, here is my reply to Aditya:

No, not everybody can do what they love. I don’t see that as a reason to avoid doing it if you can. Not everyone can be healthy either, nor can everyone can be happy, but being unhealthy or unhappy simply for that reason would be pretty ridiculous, wouldn’t it?

It is helpful to be aware of your privilege (and privilege isn’t entirely a matter of economics — the greatest privilege is to be able bodied with no serious mental illness) but I don’t understand why some people associate guilt with privilege. Most people who have privilege let it go to waste, and there’s nothing honorable or compassionate about that.

Caitlin Kelly April 21, 2014 at 7:33 am

I’ve been freelance full-time as a writer since losing my last staff newspaper job in June 2006; at 57, I doubt I’d be able to get another job, even if I wanted one. And sometimes, I do. It’s hardly for lack of the ability to discipline myself; typical workdays (sitting alone at home) are 10-5, as slavishly producing as in any office. I probably work longer hours (and am far more lonely) than I ever did in any of my jobs — I’m a fellow Canadian, so one of those was at the Globe and Mail.

I agree with many of your points but there are many downsides to working for yourself: isolation, loneliness, cashflow (everyone, fucking EVERYone in my industry thinks nothing of paying late, when bills arrive every month and must be paid on time), lack of intellectual stimulation.

The coder above raises a really valid and important point, teamwork. I recently spent 8 paid days working in the field in Nicaragua with a team of five and was much happier than I have been in a very long time. I miss being part of a team: laughs, mutual support, ideas, shared emotion about the work you’re doing.

Few jobs are ideal. Working for yourself is very pleasant for those, as I am, who are intrinsically motivated and who value — and can productively use — autonomy. But there are many other needs beyond autonomy. Negotiating $$$$ and rights with my clients has become so onerous and unpleasant and relentless I’d rather just suck up a paycheck and let someone else deal with these assholes for a while.

At your age, you have the choice to remain independent; past the age of 50, probably 45 in the U.S. where I live, good luck with that. You’re on your own — and likely earning (as I am now) 50% of my last decent salary, twice as tired for half the cash. No, not ideal. Not ideal at all.

I save 15 to 20% of my income every year, (try doing more, really, if you live in any costly area; my husband’s job is here) and it’s no fun, no matter how necessary, which it is. If all you do is work to pay basic bills and save $$$$, life gets grim pretty quick.

David Cain April 21, 2014 at 9:24 am

There are a lot of tradeoffs and many of them can’t be seen until you’re there. It can be isolating. If I don’t make sure I interact with other people, it doesn’t happen.

I think this is appropriate:


Jay April 21, 2014 at 8:31 am

I can only add my personal experience, which has many of these elements and now is going on about 7 years. One day in 2007, making six figures with two small children, I abruptly quit my mundane “brick” job – thinking this would be the push I needed to do something else, something more meaningful. Well it seems I didnt have the skills(or didnt give it long enough) to morph into a self employed role. I wasted some time, then began interviewing in the same field. Fast foward 7 years later and I’m still in the same field, three jobs later and they are pretty much the same. I disagree somewhat about children. Most probably don’t have the children to find purpose, but once you have them they do create a responsibility that keeps you in place you’d otherwise not be work-wise. Anyway, I’m now convinced that I need to develop the personal and professional skill set first before my next cornfield moment. My contentment comes from putting together actions steps every week towards my goal, my cornfield moment. Hopefully when I reach it soon my preparation will position me for long-term success. Just curious, if any others have had more success this route, or with leaving and then finding your path, having more time and focus to do it?

David Cain April 21, 2014 at 9:31 am

If you can make actual progress every week while you are still employed, then do that. My job, in its last year, became extraordinarily busy and I no longer had any energy outside of work. So instead of building my business on the side, growth kind of halted, and that’s why I quit when I did.

Kate April 21, 2014 at 8:34 am

I think work IS the new cornfield…in previous centuries, you were a farmer so you could eat. You didn’t have to like it, but if you wanted to live, you did it.

Now the corporate drone is the new farmer. (I’m one. It sucks.) And until we advance up the ladder enough to escape paycheck-to-paycheck living and put money by, there’s little chance of freedom for us – even for those that didn’t have conformity pummeled into them in school.

The best thing I can teach my children is: start a retirement fund when you turn 18. Sooner if possible.

Vilx- April 21, 2014 at 8:56 am

Have you read http://www.mrmoneymustache.com? Perhaps you could find some ideas there that would help you.

David Cain April 21, 2014 at 9:34 am

I second Vilx’s suggestion of Mr Money Mustache. How long you save for retirement is important, but how much you save (in terms of what proportion of your income) is more important.

Take a look at this:


BrownVagabonder April 21, 2014 at 8:57 am

I’m happy to hear every single time anyone has made the leap and escaped. It is like watching a movie in which you are rooting for the hero/heroine and they escape! It is gratifying and also encouraging. I’m so excited for your journey and I can’t wait to see what else you do with it. It also encourages me to keep on following my path as there is a light at the end of the tunnel. One day, I too will be able to escape from the 9-5 shindig and make my own way in life.

Michael Eisbrener April 21, 2014 at 9:10 am

This post should be required reading for everyone annually from first grade forward. Thank you David.

Jordan Bates April 21, 2014 at 9:14 am

“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.”

I’m with you as far as never making peace with that most unwelcome Pavlovian bell called an alarm clock. However, as to the next sentence, you seem to imply that *everyone* who doesn’t “escape” traditional employment ends up cynical, bored, and seeking escapism. I can’t imagine that this is true. I think there are many honest organizations for which people work and find great fulfillment. I’m still drawn to the freedom of entrepreneurship, but I’m also often attracted to professorship or being part of an inspired, spirited team working on an important project.

David Cain April 21, 2014 at 9:28 am

That is true, not everyone ends up cynical and bored. Keep in mind that I wrote this article for a magazine about escaping corporate servitude.

Garrett April 23, 2014 at 9:56 pm

For instance, I work for an organization dedicated to helping young adults transition into healthy independence. But I have to agree with David Graeber that a huge percentage of jobs are bull shit jobs: http://libcom.org/library/phenomenon-bullshit-jobs-david-graeber

Klarita April 21, 2014 at 10:02 am

I somehow, not entirely by deliberate decision, started working as a freelancer at the ripe old age of 21 :D My total experience with employment is less than 5 years before I moved on to getting paid strictly for what I actually do. I am still bound by deadlines, but I decide whether or not I want to take them on. 15 years later, I find the notion of returning to being an employee completely absurd. In fact, now I am looking for a way to work even less and enjoy life even more (although I’ve been doing pretty well as a hedonist these past 14 years – and I don’t consider the term “hedonist” an insult). And Raptitude is always an inspiration :)

Helen April 21, 2014 at 10:18 am

Interesting discussion. I am one of those people who doesn’t do well in large organisations, probably because I grew up watching my mother be ground down by one. I’ve been self-employed most of my life — plenty of stress but rarely a dull moment. I’m doing a skilled trade now so there is no real “down time”. Wherever I go, there are people who want to talk shop as soon as they find out what I do. Which also means there’s no such thing as a “staycation”. Home is work and work is home. So, unless you’re a monk or yogini, relaxation is something you mostly do off-site. So before you quit work, I urge you to open a getaway account. Every check you get for services rendered, save a little of it. When you’re young a few hours R&R will recharge your batteries. As you get older, however, a week is best.

Chris Gammell April 21, 2014 at 10:31 am

I recently made the jump myself, about 2 months ago.

It has been odd so far, I agree that every day feels like a Wednesday. I work in a field that is very bifurcated (electronics) on the job front. You either work in corporate your whole life or you are a contractor/consultant for your whole life. Making the jump was odd because there was no defined path (most consultants started that way) and not much of a support system in the middle ground. In fact, I had even asked to go part time in the interim between my switch and was outright denied. Ah well, pulled the band aid off sooner.

One piece of advice that was lobbed at me when making the transition that stuck was that you will ALWAYS have a boss. Sometimes it’s just not Bob or Sally; it’s your customers (or your freelance editors, or your consulting clients). This can be good or bad, of course. The motivation factor and the, “Oh crap, I need to feed my face at some point in the future” factor both get you moving in the morning. But customers usually do their yearly review with their dollars or with walking away and they don’t regularly remind you to finish your TPS report.

So yeah, ebbs and flows. Each has its challenges and tradeoffs. I’ve been enjoying it so far and it seems you have too!

David Cain April 21, 2014 at 7:13 pm

One piece of advice that was lobbed at me when making the transition that stuck was that you will ALWAYS have a boss.

I have heard this too and while it’s true to some extent (you are always accountable to others in some way) it really is quite different from having a boss. You design the terms, you just have to make them work :)

Einz April 21, 2014 at 10:58 am

Cheers for the nice article! Although I agree with most of what you said in this article, I find myself in a little bit of a conflict. I’m 24 years of age, I’ve been studying something where I could see myself working for a bit in the future, but it’s something I’d rather not be doing. Since I’m 4 years in, I’m just going to graduate it. For the first three years I had absolutely no idea what I’d like to be doing in the future, but now that I had a year off, it’s starting to dawn on me.. I have some sort of idea – ultimately, I want to become my own boss, but most likely not doing what I’m doing now. That’s is engineering. The plan though is to get my first proper job experience in engineering, use the perks of the high salaries and make my degree count, but while doing that I hope to start taking baby steps working on my own dream – that is to become my own boss, and hopefully get my thing working. Nevertheless I will try hard at my 9-5 but I believe to be far more productive working for myself.

David Cain April 21, 2014 at 7:14 pm

I think everyone has to go through an “I don’t know what the hell I’m doing, so I’ll just do this for now” phase. Maybe all the phases are like that… :)

Michael April 21, 2014 at 11:17 am

At 42, I’m now 8 years free from 9-5 (well, 7-6 actually… I envied the 9-5’ers). Best thing I ever did.

It did take time to overcome that “I’m doing something bad” feeling! And “cave-man-ism” did set in. Not just shaving weekly instead of daily but mentally “not shaving.” Like what happened to Michael Keaton’s character in Mr. Mom.

My top 2 tips on how to stay sane:

1) Go to the gym everyday:
a) Your body needs it, especially if you’re keyboard-bound most of the day.
b) Your mind needs it … endorphins, seratonin, etc.
c) There are people there.

2) Keep a simple to-do list:
a) Cross off at least 1 or 2 small items each day.
b) Do at least 1 hour of work on your “main” thing.

“If one advances confidently in the direction of his dreams, and endeavors to live the life which he has imagined, he will meet with a success unexpected in common hours.” ~Thoreau

Mel Tan April 21, 2014 at 11:21 am

It’s a nice article that you wrote and I think it’s a meaningful expansion for yourself. Although I don’t think your experience is necessarily the same for everyone else.

I am travelling right now in Vietnam and there are many people struggling just to make a living, and put food on the table. I think your case my apply mostly to westerners in a privileged position. I think the Vietnamese also have goals, but their 8h/5d workday or sometimes even 16h/7d is a means to an end. It may be their children, it may be for their grandparents.

Not everyone finds joy in farming, ensuring plumbing in our homes work, generating electricity, etc. but someone has to do it or we all will have issues.

I like what I do… sometimes it’s 9-5, sometimes it’s 70 hours/week. I would rather see work move towards result oriented rather than numbers of hours for those in the knowledge worker field, rather than factory production style… but contracts don’t seem to be written up that way for individual contractors.

P.S. I have been a independent contractor for 8 years. I’m converting back to an employee for a period of time because it will help with my goals. Just because you work 9-5 doesn’t mean that a person inherently has no goals.

I hate the new find work you love mantra right now because it actually devalues a lot of work people do. That love and fulfillment should be all that someone gets paid if it’s something they love to do.

David Cain April 21, 2014 at 7:17 pm

Everyone’s experience is different, of course. Keep in mind this article was written for a magazine whose readers are typically white-collar aspiring corporate escapees.

I don’t agree with the (increasingly popular) argument that looking for joy in your work somehow “devalues” unglamorous work. In fact I wrote an article about it here:


Jacqueline Golightly May 7, 2014 at 6:37 am

Maybe the trick is to try and find joy and value in the unglamorous work. My son is a severely autistic 21 year old. He is 6ft tall and powerful.

There is nothing more unglamorous than wiping a man’s backside or brushing his teeth or shaving someone using who is using their fists to stop you. However, I totally get what doing these things for him provide his life with. Being clean and comfortable are fundamental to his wellbeing. My job has immense value and therefore the task isn’t glamorous or even joyful but is is deeply satisfying.

We’re missing a point if activities are abitrarily defined as joyful or glamorous and I don’t think David is making that distinction. Being satisfied that the work is worthwhile and that by doing it you’re making a difference is perhaps the key to finding peace with life.

Dakota April 21, 2014 at 11:36 am

Great article! I absolutely agree that the system we grow up in does not prepare us to be entrepreneurs. When I quit my engineering job six years ago and struck out on my own, it took over 9 months before I created anything that adhered to my values and used my skills. I’m lucky to have built a business that survived the brief depression and succeeded beyond my expectations!

The section of your post that spoke most to me was escaping the vapidity of work to have children, which I totally agree with. That takes a lot of courage to say, and I’m glad you haven’t taken a bunch of flak for it – that says something about your readership! My wife and I are in the stage of our lives where everyone we know is procreating, and we’re on the “no” side of the fence. We’re financially solid and can now do whatever we’d like with our skills and time thanks to my business and using Mr Money’s techniques for FIRE. Such a good time to get out and change the world ourselves, rather than raising an eco-warrior.

Keep up the great writing. It has been fun following your journey!

amy April 21, 2014 at 12:46 pm

Thank you for the excellent article. What you describe is exactly why I chose to homeschool – and further, to unschool – my daughter. Now at 14 she wakes up (when she wants, which is weirdly at dawn) and knows immediately what she want to do for the day. She is an artist and spends many hours painting and drawing each day. She has chosen to take a couple of community college classes to increase her skills. Of course, she does not have to support herself so the choices are perhaps easier for her. I think the important thing is that she does make choices, she likes to be busy, and her choices, for the most part, are pretty smart.

My husband had always been a self-employed musician, very disciplined and in love with his work. My daughter has a good example!

The part you wrote about having kids struck me pretty hard. I like my job, but I am not passionate about it. I have no idea what my passion is, aside from my daughter. And that is kind of sad.

Morgan April 21, 2014 at 1:06 pm

There’s nothing sad about having your main passion be your daughter. We should be so lucky to live in a world where more people made your choice. It sounds like you’re raising a kid who will know exactly what her passions are (if she doesn’t already).

My wife and I both quit our jobs as public school teachers after 10 years to be home with our three kids. Our new “job” is raising resilient, happy, functional humans that will be a net positive to the world and we’re really good at it, and it sounds like you are too. To fund this “job” we sell stuff on Etsy. We’re OK at that. That’s fine, because it’s just a means to an end.

Our income was immediately cut in half, but somehow we have more left over at the end of every month. Hmmm…. More importantly we’re more content and calm than everyone we know that’s still in the profession.

I think you found your passion.

John April 21, 2014 at 2:22 pm

David, I catch your drift in this piece. However, I think it gets a bit sticky when talking about parents’ guidance. Parents that care will teach you right from wrong and genuinely want to see you succeed. Something I’ve noticed since I’ve been away from home now for 7+ years is the fact that many of my viewpoints have differed from my parents. I have a dichotomy in my mind that struggles when I go back to visit: do I voice my different opinion and risk offending them or simply act like I agree? I’ve learned that the basic structure they gave me was awesome, but it’s hard to follow their bias and advice all the time now that I’m older.

David Cain April 21, 2014 at 7:22 pm

I remember how good my dad was about not telling me what opinions to have. He would always say something like “Some people think X, and some people believe Y.” He was definitely very opinionated but I was aware that he would prefer I think for myself than agree with him.

tallgirl1204 April 21, 2014 at 3:29 pm

Thanks for this. You have put into words a primary difference between my husband and me– I adapted early and well to pleasing my teachers, my professors and my bosses. My husband was a rebellious student, a terrible soldier, and worked in a trade where he primarily worked independently. He lived simply, saved $$$, stepped in and out of working when it was convenient, and when we met and had a child, he was only too happy to become a SAHD. He does way better at it than I would– he enjoys the freedom he has to plan his own days, and he still will take on trade work IF he likes the person, approves of the project, and can bring our child along. Otherwise his days are full, Mr. Money Mustache-style, of raising our kid, gardening, house remodeling, and helping friends with projects.

I have never understood his cavelier (sp) attitude toward authority and structure, but your article is helping me how the rebellious 3rd grader became the man– and it also helps me appreciate his determination that our son also choose how and when he will submit to authority. I had never heard it all put together so clearly.

h April 21, 2014 at 4:02 pm

You should read “Doing Nothing” http://www.amazon.com/Doing-Nothing-History-Loungers-Slackers-ebook/dp/B003GY0KS4/ref=sr_1_2?ie=UTF8&qid=1398113856&sr=8-2&keywords=doing+nothing

It is an interesting take on what it means to do “Nothing”, and how hard it can be.

I understand that you are trying to do Something, but sometimes it’s good to understand a thing in terms of its contrast.

Cascade April 21, 2014 at 4:56 pm

As a person aspiring to be a concept artist in the game industry, this is a very good wake up call. I adore all your articles!

Franko April 21, 2014 at 6:19 pm

How about everyone takes a turn at cleaning the toilets and do your own rubbish, jesus its simple!

David Cain April 21, 2014 at 7:25 pm

I spent time cleaning toilets for a living. And picking fruit and shoveling dirt and hammering stakes and lifting boxes. I think it’s good to do something awful at some point.

cooperzale April 21, 2014 at 8:30 pm

We are sucked into a conventional wisdom and path of least resistance around ranking, hierarchy, and privilege!


Drew April 21, 2014 at 11:38 pm

The trick is to “do something” just long enough, until you can afford to quit and “do nothing” (or at least transition to doing less). How long is long enough? Well, that depends on how adept you are at avoiding the pitfalls that consign you to a life of servitude in the Salt Mine.

I’m actually ecstatic that so few people realize this. There needs to be a class of people who are hell-bent on shopping their way to happiness…boats, RVs, bigger TVs, bigger houses, more furniture…bring it on! Without people who are slaves to their consumption, nobody would be left to do the programming and pick up the garbage, and nobody would start the public companies that sell truckloads of stuff to the crazed masses, thereby creating opportunities for Escapologists to invest in dividend stock.

Soma April 21, 2014 at 11:43 pm

Ever since I discovered it, Raptitude has had a strange and comforting synchronicity with the events in my own life–I find this article on my first day of funemployment, after spending the weekend having a similar revelation: that this is the first time in my twenty-nine years that I am truly in charge of my time.

And so far, it feels right.

Jacqueline Golightly May 7, 2014 at 7:03 am

I just found my job description…funemployment should be one aspect of a new careers training scheme for school leavers. It seems odd that we’re taught academic skills but so much misery is caused by poor financial acumen. If young people could be made more aware of how the cost of something impacts on all areas of their happiness and wellbeing then more people may be able to have fun and follow their dreams. Understanding APR, compound and cumulative spending etc could give so much more to a young person’s life choices than knowing what crop rotation is!

Luke April 22, 2014 at 10:17 am

I used to work a very strange part-time schedule that involved graveyard shifts on Friday and Saturday nights. I had an incredible amount of free-time – the most free time I’ve ever had as a working adult – and I was pretty good at using it productively. I ended up making more art and music than any other point in my life. But I was on the exact opposite of the conventional schedule, so pretty much all my free time was spent alone, and that ended up taking a huge emotional toll. My girlfriend, friends and family all worked normal 9-to-5 schedules, so during their weekends I was always either working or sleeping, and eventually it really got to me and I began to feel really emotionally messed up (though I’m sure the unnatural sleep cycle had a lot to do with it too).

For me, that span of time brought into the relief the fact that in the modern human world, individualizing your life necessarily ends up involving a component of self-exile. Being any “nonconformist” and being a “deviant” end up being very close to the same thing, practically speaking.

And its not just the logistics of schedules either. When you’re doing unconventional things with your time, you find that you have a lot less common ground with your friends. Nowadays, when my friends get together to hang out, the main subject ends up being what we’re doing at work, trading stories and funny observations, and all venting to each other about the daily grind. When you break away from that but your peer group hasn’t, you lose a significant solidarity with them (this was even true when I was still working but doing really unconventional work, so I imagine it would be more true with self-employment). The more unconventional your pursuits become, the more common ground is lost.

Solidarity is a very emotionally valuable thing to have in life – in my opinion, the loss of that solidarity is an even bigger potential dilemma of “escapology” than the loss of regimen, because it seems possible to recover a sense of regimen through retraining. To regain solidarity in the same way, you’d have to take everyone else with you…

Eric April 22, 2014 at 11:14 am

Hey, I have same feeling about jobs, and I have similar experience about escaping. I am very agree with that: make a long term plan, find something you love and valuable to others to do.

Elizabeth April 22, 2014 at 1:00 pm

It’s very true that the greatest privilege is to be able-bodied. The last time I had a real full-time job was 2010, but for a few years after that I made a decent living doing contract work. My sole job duty was staring at a screen and clicking a mouse, and of course I didn’t have any health insurance. I was spending most of my disposable income on chiropractors and physical therapy, and I had the kind of RSIs you would normally see in a garment factory worker. The employers told me to shove it when I asked for disability accommodation, and I realized that if I didn’t stop I was going to need hand surgeries that no one would pay for. I realized that I kind of liked having sensation in my fingers and that the only way I could protect my health was to control my own work situation. Employers only “care” about your health to the extent that it affects their workers comp premiums or the amount of widgets you produce. They really don’t give a crap about the long-term damage they’re doing, because by the time it hits you will probably be gone and it will be too late for you to sue them. Conclusion-opposable thumbs are a terrible thing to waste.

Kabamba April 24, 2014 at 5:54 am

Yesterday I mentally gave myself anther 10 year before trying to escape. Maybe I need to reconsider. :-)
This is a brilliant article this one is.

David Cain April 24, 2014 at 1:24 pm

Ten years is a long time and anybody’s life will look really different then than it does now. I’m sure you will reconsider many times over the next decade whether you plan to or not :)

But I do think escape is something that should be done on a long timeline. It allows you to arrange everything to your advantage. I wish I’d started planning ten years ago.

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:


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 (http://livingeconomiesforum.org/real-wealthliving-wealth) and less on what he calls phantom wealth (http://livingeconomiesforum.org/phantom-wealth).

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: http://www.neweconomics.org/publications/entry/a-bit-rich.

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.

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!

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 (http://www.neweconomyworkinggroup.org/visions/living-wealth-indicators/gdp-flawed-measure-progress). 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: http://www.jeffvail.net/2006/04/envisioning-hamlet-economy-topology-of.html. And this: http://www.jeffvail.net/2006/04/rhizome-central-place-theory.html.

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: http://www.resilience.org/stories/2013-09-03/our-democracy.

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.

Jacqueline Golightly May 7, 2014 at 7:12 am

Mark..you wrote exactly what I was thinking…I just couldn’t get it down! Thank you.

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.

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…

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 :-)

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.

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: http://koobazaur.com/freelancer-tips-for-getting-work-done-while-keeping-your-sanity/ .

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.

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

Lien June 1, 2014 at 1:12 pm

Hello, Neat post. There is a problem with your website in internet explorer, would test
this? IE nonetheless is the marketplace leader and a good part of other folks
will omit your fantastic writing due to this problem.

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.

Comments on this entry are closed.

{ 12 Trackbacks }

Desktop version

Raptitude is an independent blog by . Some links on this page may be affiliate links, which means I might earn a commission if you buy certain things I link to. In such cases the cost to the visitor remains the same.