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.