Why did I chain myself to work, and do I let myself go?

When I was 19 years old I went full-throttle into the corporate world. The internet boom was a massive wave rolling over the planet and I had a surfboard: skills to build technology that businesses were desperate for. At that young professional age, I knew more about the internet and systems than most working adults. Tech was my obsession – it was pure luck to be at right place and time, with the right interests. The job market accepted me with open arms.

Initially no job felt like “work”. It was an opportunity to learn, play, and grow. It was fun to routinely impress employers and colleagues with what I could make technology do, or solve problems that seemingly nobody else had the will or interest to. Each day was a competition with myself to be better than the day prior. Success was validated through promotions, awards, and new job opportunities. The majority of my mental experience was flow state. As a result, my work ethic was insane.

Nearly two decades and hundreds of technology projects later, having worked in a variety of businesses and industries, I sit here reflecting on how my motivation and reward system has shifted over time. Gradually, the fun game I started my career with morphed into management responsibilities, more noticeable stress, and 20+ year commitments to pay debt. I no longer begin most days with deep enthusiasm to learn and create things, but rather, immerse myself in risk governance responsibilities… risks *I* am responsible for bringing into the world as a consequence of technology I created, and managing teams of people I hired. Do I miss the fun – is that the source of an impulse to leave? In a small way, yes, but in the big scheme no – the fun was merely a means to arrive here.

In the spectrum of human suffering, am I in great pain? Is my life threatened? Clearly not.

So what’s the problem?

Now that I more fully comprehend what a traditional “full-time job” is – everything that it provides and does not provide – is this really the bargain I wanted to lock-in through age 65? Don’t we all have a deep obligation to explore various aspects of ourselves, and therefore need be honest and acknowledge when that process is stuck or severely limited by the constraints of our current life template? Deep down, intuitively, there is great protest and resentment in ignoring this dilemma. The conclusion now seems obvious – ANY traditional job will command 40-60 hours (or more) of the best hours of your life, per-week, until age 65, which does not offer the vast open space that is most conducive to creativity, free thinking, self-discovery, and deeply immersive passions. Is that not insane?

Let’s explore the obvious reflex-arguments against this epiphany:

Counter-Argument #1 – Deep satisfaction and self-development occur as a byproduct of passion – therefore if you “love your work”, you find harmony. It’s time to change jobs.

Is it the job I have right now? One might suggest a job change is in order – to bring new challenges, growth, and satisfaction. The truth is I’ve done that before… 6 or 7 times. While yes, it is wildly invigorating to start a new job and climb another rung, I would counter that’s not scratching the real itch here. I would agree that sure, if one is lucky and deserving, a job *may* provide: skills, character development, intellectual and creative challenge, a community, a feeling of contribution to society, a roof over your head(s) and full belly. In my case, fortunately, all of those boxes are checked. But are these really all the spokes on the wheel of life and human potential? And if you agree that they are not, can you really thoroughly explore the other spokes with your remaining free time? I would argue that true discovery takes more time, space, and reflection. Which brings me to the next counter-argument…

Counter-Argument #2 – Time management is the issue. To explore your inner-life more fully, optimize your use of free time on nights, weekends, and vacations.

OK, let’s do some SIMPLE math. Let’s assume you get ~7 hours of sleep per night, and devote ~10 hours per day to work (including preparation, commute, small breaks, and emailing off-hours). This obviously varies from person to person, but it only needs to be approximate for this point. If we view our week as a 168 hour pie… let’s see how much we actually get for ourselves in a typical full-time work situation. ~30% (48 hours) is sleep, ~30% (50 hours) is work, and ~40% (70 hours) is “Free” time. 70 hours of Free time per week… sounds great, right? An emphatic NO, from me. That number is deceptive… “Free” time is NOT equal to “Golden” time – when your mind is at it’s absolute best, fully committed to what’s in front of you. Where does Golden exist, then? Mostly at work, then the weekend.

• Out of 70 Free-time hours, 35 of them are scraps on workday mornings and evenings. In the morning, you may be at your best, but your mind is most likely dominated by the work day ahead. In other words, not the best time to learn that new language or immerse yourself in playing piano. You can force it, of course. Then, in the evening, you are exhausted, head full and spinning from the day. After you’ve run a mental marathon, do you really have remaining brain juice for personal endeavors? And if you do, will you be your best?
• The other 35 hours of “Free” time falls on our beloved weekends. We all know – Saturday is a slice of heaven — from the instant we wake up, there is potential to spend every waking minute focused outside of work. Sunday is ALMOST as wonderful, were it not for the fact that come evening time, we automatically start thinking about the day ahead…

My point: Weekday “Free” (35 hours per week) time is junk. Fragments. It’s better than nothing, but a lot of work to take advantage of for very little return. Weekend “Free” time on the other hand is golden, right? But it’s SO scarce – over the course of a lifetime. That segues to one more important point I want to make about free time: From personal experience it takes at least 3-4 consecutive days to *truly* disconnect from a stressful job and set your mind free. This is what makes vacations so simultaneously sweet and disturbing. In one hand, when you finally feel relaxed, there is nothing better. In the other hand, how can you not ask yourself: why do we organize our lives this way, to only experience this a few times per year? Bottom line – the majority our free time is delivered in microdoses. In the long run, using this time to explore personal potential is akin to filling an Olympic swimming pool with an eye dropper.

Counter-Argument #3 – First world problems… It is a privilege to contemplate from this position. You are ungrateful.

Is this a failure to appreciate all of the comfort, safety, and security I have in my life? Am I betraying my colleagues, professional friends, and insanely privileged western society with this contemplation? On the contrary, I am extremely grateful for all opportunity I’ve been given, and have expressed that gratitude with unconditional commitment to my professional life for two decades. I understand sacrifice and hard work – 90 hour work weeks, chasing professional accomplishments with superhuman conviction, to the point where the “work” has been at the center of my psychological universe. At the heart of this reflection, though, is an important question that calls out to everyone at some point: what’s this life all about? For me, the aim of well-lived life MUST sit beyond comfort, security, and professional accomplishments. Further, this aim sits in contention with the traditional work/life template. This is something I feel called to examine and resolve. This is not about being grateful or not.

Rage against the machine – Is the “System” to blame?

What do I do with this conclusion? Blame the system, start a Fight Club and tear it down? No – as much as I believe the capitalist “system” lures us toward being myopic cogs in a machine that grinds away until we’re old, I don’t believe a bunch of evil geniuses are wishing this destiny upon us. (For example: The owner of my company, an amazing, good, genuine human being who wants to do right in the world. Grinds away at work, day in and day out, just like me. Is he taking advantage of me? No… he’s in the same boat — an equally devout member of this business religion.) Additionally, the “system” is what enabled me to learn skills, go into the world and get paid for those skills, and earn the privilege to sit here and write this. It’s not that the system is purely evil, rather there are ruts in the system to be very cautious about. It’s too easy to go sailing through life not understanding what happens when you get on the conveyor belt of adulthood. You’re on the belt excited to have income, your lifestyle inflates, you have debts to pay, and maybe you have dependents who rely on you. You accept the bargain of renting your mind/body until you’re cognitively and physically declining. Along the way, you’re tired, deprived of head space, filling the little free time you have with obligations and infinitely available options to tune out. Maybe you never had the luxury to recognize there was another option on the table. If only this were easier to grasp sooner. If only there was a mid-life mulligan for everyone. Even so, I do believe we possess the freedom to recognize and change things, if we wish.

If everyone thought this way – how could society function?

OK – so everyone break off the shackles of their 40+ hour work week to “contemplate existence and explore themselves”. What happens to the doctors and nurses? the policeman? All public services? What happens to Amazon prime, the grocery store, pharmacies, essential workers, everything society depends to run like clockwork, that currently relies on humans to show up, day in and day out, and do their part? Great question. What I am NOT suggesting is that everyone simultaneously wander around soul-searching for their entire lives. I am speaking after working for 25 years. It seems fair that every member of society must pay their dues somehow – contribute to the world while supporting their life. (Note – this is where socialism can creep in, which I am not advocating. I am in favor of governing capitalism to take care of people). My essential claim here, is that it seems way too easy to get stuck with the wrong priorities, and it takes a lot of effort and honesty to even notice when you do. There is no warning, no built-in release valve. The goal-post is: work till you’re 65. I wonder if there’s another way to construct society so everyone would get this benefit without having to have some sensational epiphany in mid life. It’s easy to understand why people often wonder about it. It’s easy to understand why sabbaticals exist, and why some companies are experimenting with a 4-day work week in an attempt to rebalance things. These are not widely available privileges. Perhaps they will be someday.

What now?

It seems the only choice for anyone in this position is to impose their own will and chart a new course. To where, it’s impossible to say. Something along the lines of living minimally and letting the mind roam. Paradoxically there is no map, and it’s hard to see very far in any direction until your boat is already unmoored. The only certainty is if you change nothing, then nothing will change. While the traditional lifelong slot in the capitalist machine will keep one fed and safe, and satisfy a few hedonistic desires of choice, it will infinitely accept one’s energy and cannot deeply nourish one’s soul in return. It can only provide narrow growth and financial wealth. One must be not be tempted to reside permanently here, but rather, remember it’s merely a utility to support a grander journey of life.

It is deeply unsettling to look out onto the horizon of your life and see nothing but a straight road that never turns and clear skies. Life without struggle, growth, and lighting-up undiscovered dark rooms in the metaphorical castle of the mind, is missing something. An abundance of safety is a pernicious threat to a life fully lived.

Related:

(One Year Later 👆)

Quotes on “Work”

“The difference between selling yourself into slavery and renting yourself into slavery in the ancient world was basically none at all, you know. If Aristotle were here, he’d think most people in a country like England or America were slaves.”
– David Greaber

“Unfortunately, too many people get caught up in insecurity throughout their lives, and stay there, missing out on the immense beauty in the world that is still left to explore and the possibilities for their own self-actualization and, ultimately, transcendence. We miss the ocean for the waves.”
– Scott Barry Kaufman

“How we spend our days is, of course, how we spend our lives. What we do with this hour, and that one, is what we are doing. A schedule defends from chaos and whim. It is a net for catching days. It is a scaffolding on which a worker can stand and labor with both hands at sections of time. A schedule is a mock-up of reason and order—willed, faked, and so brought into being; it is a peace and a haven set into the wreck of time; it is a lifeboat on which you find yourself, decades later, still living. Each day is the same, so you remember the series afterward as a blurred and powerful pattern.”
– Annie Dillard

“‘Slavery resides underneath marble and gold.’ Too many successful people are prisoners in jails of their own making.”
– Seneca (shared by Ryan Holiday)

“Most Americans, are deep in unnecessary debt, overweight and poorly nourished, inactive and stressed out, and self-sentenced to a mandatory career of unsatisfying work just to stay afloat. We constantly buy things we can’t afford and don’t need, and the majority of the trading we do does not increase our net happiness. And all of this is done with virtually no awareness of how we are affecting our own ecosystem – the tiny veneer of air and plants that is the only thing between us and the lifeless vacuum of space. In fact, it would be difficult to imagine a less efficient way to maximize “Utility” than what the modern consumer does.”
– Mr. Money Mustache

“We have got a system of schooling which gives it a completely different impression. It’s all graded, and what we do is we put the child into the corridor of this grade system, with a kind of “Come on, kitty – kitty – kitty.” And you go to kindergarten, and that is a great thing, because when you finish that you will get into first grade; and then “Come on!” First grade leads to second grade, and so on. And then you get out of grade school, you go on to high school, and it’s “revving up,” the thing is coming, and then you go on to college, and by Jove, you get into graduate school, and when you are through with graduate school you go out to join the world. And then you get into some racket where you are selling insurance and they’ve got their quota to make, and you’ve gotta make that. And all the time that thing is coming, it’s coming, it’s coming – that great thing –the success you are working for. Then when you wake up one day, about forty years old, you say, “My God, I have arrived! I am there.” And you do not feel very different from what you always felt, and there is a slight let-down because you feel there’s a hoax. And there was a hoax, a dreadful hoax: they made you miss everything by expectation. Look at the people who live to retire and they put those savings away, and then when they are sixty-five they do not have any energy left, they’re more or less impotent, and they go on and rot in an old people’s – senior citizen’s community. Because we simply cheated ourselves the whole way down the line. We thought of life by analogy with a journey, with a pilgrimage – which had a serious purpose at the end. The thing was to get to that end, success, or whatever it is, or maybe Heaven after you are dead, but we missed the point the whole way along.”
– Alan Watts (youtube version) (Branson reference)

“A friend of mine was working his ass off. I asked him: what’s your work life balance? He said ‘Work 80%, Family 20% and then I try to find some time to sleep.’ There’s no personal time, there’s no passionate time. Young people are often passionate about work, but you need to have some space in your life for things. You have to get to know yourself; Why does the mind think certain things? Why do you do what you do?”
– Jim Keller (Lex Fridman podcast)

“Most of our lives are spent finding parking for the job we don’t want to do. Melanie is not alone in that. And after any number of years, those routines accumulate. And that’s more or less your life.”
– Jay Caspian Kang – The Walls Close In

“I think the pervasiveness of feeling like work is a thing that we have to shut-off from – a thing that we can’t be our best selves – a thing that we have to get through on the way to the weekend – I think that is a humanistic sickness.”
– Dan Cable

“Aristotle thought there was a danger of our lives focusing on telic activities; a means to an end. The way he puts it is: ‘Work is for the sake of leisure, not the other way around’. We have a tendency to get locked into this mode where we are acting for the sake of something else, without ever getting the ‘something else’. Part of my work is trying to do, is to ask people to reflect on what the ‘something else’, is? What’s the thing that all of your busyness and acclivity is really for?”
– Zena Hitz

“A very common thing I hear [on regrets] is retirement. People will have worked really hard, set a retirement date, and then have often felt that their retirement had been ill health and they haven’t had the time to spend doing the things they’d hoped to.”
– Hospice Nurses, patient’s thoughts before death

“If you ask the worker what he thinks the best part of his life, he is not likely to say: “I enjoy work because it makes me feel that I am fulfilling man’s noblest task, and because I like to think how much man can transform his planet. It is true that my body demands periods of rest, which I have to fill in as best I may, but I am never so happy as when the morning comes and I can return to the toil from which my contentment springs.” I have never heard workingmen say this sort of thing. They consider work, as it should be considered, a necessary means to a livelihood, and it is from their leisure hours that they derive whatever happiness they may enjoy.”
– Bertrand Russell

“Presence is far more intricate and rewarding an art than productivity. Ours is a culture that measures our worth as human beings by our efficiency, our earnings, our ability to perform this or that. The cult of productivity has its place, but worshipping at its altar daily robs us of the very capacity for joy and wonder that makes life worth living.”
– Maria Papova

“There is a growing apprehension that existence is a rat-race in a trap: living organisms, including people, are merely tubes which put things in at one end and let them out at the other, which both keeps them doing it and in the long run wears them out.”
– Alan Watts

“I worked for corporate America for twenty years. My friend Bill worked for the same company and he had liver failure. A week before he was about to retire, HR called him, in hospice, and said ‘let’s talk about your retirement!’ He died ten days later… having never taken that sailboat he bought out of his driveway. He missed out on everything. He told me before he died ‘just don’t waste any time, Merle. Don’t waste any time.’ So I retired as soon as I could. I didn’t want my sailboat to be in my driveway when I died.”
– Nomadland

“You know my old saying, “Slavery was never abolished, it was only extended to include all the colors.” And what hurts is the steadily diminishing humanity of those fighting to hold jobs they don’t want but fear the alternative worse. People simply empty out. They are bodies with fearful and obedient minds. The color leaves the eye. The voice becomes ugly. And the body. The hair. The fingernails. The shoes. Everything does. As a young man I could not believe that people could give their lives over to those conditions. As an old man, I still can’t believe it. What do they do it for? Sex? TV? An automobile on monthly payments? Or children? Children who are just going to do the same things that they did? […] I still feel that something in me is going to remember (no matter how far I’m gone) how I’ve come through the murder and the mess and the moil, to at least a generous way to die. To not to have entirely wasted one’s life seems to be a worthy accomplishment, if only for myself.”
– Charles Bukowski

“I’m pretty high on the idea that maybe wage labor is an intermediate step in human society and wouldn’t it be great if we got past the point where it was widely needed. But that is much more a cultural question in the worlds we’re talking about here than it even is an economic one.”
– Ezra Klein