Earning my bread
On work, money, and escaping the machine from the inside
This is part of the third writing series by a group of men writing on Substack that includes myself,, ,, , and . This series is about work and money.
I was around nine years old when I began to wake at five AM, and roll out of bed and down the front stairs to wait in the fog for the sound of the boxy brown Chronicle truck grinding up the Sanchez Street hill. The guys in the truck would drive around with the sliding door open, and as they rolled past my corner without quite coming to a stop, a warm bundle of morning papers would thump onto the concrete sidewalk at my feet, ready for me to fold and band before starting my route. That was the same year that I went to City Hall to get a business license so that my friend Zach and I could do business by mail with TSR Games for Dungeons and Dragons dice and books, filling orders from our classmates and that we recorded on a ten-cent carbon-newsprint notepad.
The money I earned from the paper route and our little mail-order business went to packets of Hubba Bubba and Now ’N Laters, 12 ounce bottles of Coke, quarters for the video arcade, and skateboard wheels. I suppose my sister and I did get some sort of allowance, but I’d already figured out that if I really wanted much freedom in the world—especially as a city kid growing up in San Francisco and not somewhere out in the countryside—I needed my own money. Cities are born of commerce, and cash is the blood that runs in their veins. There’s nothing to hunt or forage. I got the message from the start: everything takes—or makes—money.
Although usually equated as roughly synonymous, making money isn’t the same thing as work. I never thought of myself as particularly driven, and I was not the type to put his nose to the grindstone in an effort to prove my moral fiber. I have put in long hours at some points in my life, but there’s a difference between earned compensation and the way work works—and whether you’re working for yourself, or someone else. I don’t mind doing the work, but the idea that we’re supposed to just sign up for some job—they used to be listed in the classifieds, in the back of those same papers that I delivered—and spend most of the hours of most of the days grinding away in exchange for a paycheck always seemed suspicious, at best.
I mean, really, my work-related motto has always been “fuck work,” meaning at the very least that work sure shouldn’t suck, and also very much that working full time is far from ideal, healthy, or even sane. Still, you have to have your shit together. You gotta pay the bills—and then somehow manage to get ahead, at least in the long run. Nobody else is going to do it for you. It’s every man, woman, and child for themselves here, with very few exceptions.
I’ve had some bullshit jobs, like filling in spreadsheets in a factory that made those sickly-sweet flavored syrups used to make so-called Italian sodas and flavor the ice-cream sundaes that pass for coffee drinks at chain cafes, but overall, I’ve had a hand in writing the description for most of the jobs I’ve ended up with, and far more of my work has been self-employed or running the very modest little business that I started back around Y2K and managed to sell in 2015. The fact is that by focusing on earning and freedom—and also by not having kids or ex-wives, and by living fairly cheap—I managed to move on from the conventional working world then, at the age of forty-five. It’s not that I was suddenly able to never work again, but the offbeat, unplanned entrepreneurial program that I somehow cooked up from an early age worked well enough that, by now, I’ve been outside the machine for most of my life.
That said, the reason this has all been on my mind lately—and also for the extended hiatus from the keyboard (thank you, dear readers and subscribers, for your patience)—is that, guess what, I got a job! I wasn’t really looking, but I had been feeling more and more the inescapable truth that despite what I managed to sock away, I’ve only had a trickle of income for nine of my so-called prime earning years. And y’know what else? The life of a writer can be pretty lonely—and pretty self-centered. I was getting a little tired of my own voice, and as the end of last year approached, I found myself wishing for an opportunity to get involved in something other—and larger—than my big ole bear self.
I don’t know if it’s really true, but it’s always felt to me that as often as I’ve heard of others getting invited to join some promising enterprise, it wasn’t ever me being asked. I’m sure that part of the reason is just that I don’t know enough rich people, and that only those of us who have already achieved an unusual degree of financial success can even contemplate making a salaried invitation, but it’s also because of how we all tend to compete more than cooperate with one another—perhaps especially as men.
As much as I’ve sought collaboration over the years, it’s been very, very rare to get past the point of ideation into anything like co-creation with another man, due to a potent combination of need, striving, ego, and envy. True or not, another man’s success often felt like it came at the potential expense of my own. After years of working on building closer relationships with other men, I find that this feeling has been mostly replaced by the warmth of brotherhood, and I find myself less interested in spending time with guys with whom it still surfaces.
And so, what a delightful surprise and striking contrast to find myself on the receiving end of what I’ve so often wished for—an invitation, in the form of a request for help—and not just for the pleasure of being of assistance. I know we’re all supposed to know what we want to do, and I sure have spent plenty of time trying to figure that one out! I’ve also spent plenty of time doing exactly—and only—what I want to do, and yet now, with this new gig, I find myself in the middle of something not entirely out of the realm of the imaginable, given my history as a San Francisco native, a lover of cities and geography, a student of urban planning, and as an entrepreneur—but that just appeared along my way, unplanned and unexpected. Very much as I was wishing for, working as part of someone else’s business for a change defocuses me and instead puts me very much amidst the turning of some other set of gears.
In Michael Singer’s The Surrender Experiment, he describes himself as someone who “tried as hard as I could to break free of myself for years” with meditation and other spiritual practices, but who didn’t find a deep and lasting freedom until he applied that same paradigm of selfless surrender to unforeseen, and even unlikely invitations in the realm of work.
In America, we’re expected to craft a path entirely of our own making, with the assumption that not only is this the right and best way to achieve our own happiness and fulfillment, but also that of society as a whole. As I think anyone who’s been around the block a few times knows well enough, things don’t always work out that way. Both Stoicism and Daoism offer remarkably similar guidance that takes us in a very different direction in our search for meaning and purpose: as long as we manage to live well and find a way to be useful, that search is effectively fulfilled. It doesn’t always have to be about me.
In much more everyday terms, it sure does feel different to have some money coming in again. After years of feeling like a strange combination of made guy and ever-so-slightly skint, I’m free again to step out in the city, fill the tank, buy a round, and even go on a trip that involves booking a hotel instead of just sleeping in my van. It feels different, and it feels good—and, especially coming back to the world of work after such a long hiatus, it’s very clear to me that a big part of what feels good comes from being able to spend money on conveniences that are largely compensation for having to spend so much time at work in the first place.
I can afford to spend twenty bucks for lunch sometimes as opposed to eating rice and beans four days a week—but I like rice and beans (nothing wrong with the Nicoyan diet!)—and the whole reason that I end up eating out more often now is that I’ve traded some away some of my cooking time for work time. Much the same, I’m more aware than ever that my desire for little treats like a groovy Lion’s Mane latte, an after-work drink, or an hour-and-a-half massage on a Friday evening is largely due to the need for some relief from the tax that work extracts, no matter how interesting or engaging, or how grateful I am to have been asked.
Earning money from anything not closely related to writing might take some of the shine off of the life of a writer, but it can also be precisely that which enables the life of the writer. We all need grease for gas and grub, and I’ve always appreciated the common-sensical “barbell strategy” as advised by Nassim Taleb for writers in particular: “…look for a sinecure…then spend their spare time writing, free to write whatever they want, under their own standards.” What he calls the “businessman-scholar situation” certainly seems more workable than the much– and mistakenly– romanticized myth of the starving artist—and this is the path that I’ve followed myself, although I’d chalk it up more to a lack of courage and imagination as a younger person than any sort of plan in particular. I don’t know whether Chuck Bukowski would say that he chose to work as a postman until he could make enough to survive as a writer, or whether Henry Miller’s side gig as a fortune teller quite qualifies, but these are just two of many, many examples. In my reading, it’s actually much harder to find anyone who can claim to be pure in their pursuit of their art. Perhaps the distinction is meaningless—after all, one of the practical definitions of when art becomes real is when someone else is willing to pay for it.
At least for me, it’s also something of a question of discipline. While living cheap and dedicating oneself to the art certainly feels like a harder go, the reality is that even working half-time distracts me enough from the creative realm that it requires another measure of determination to work enough to make life easier and still actually get any writing done. As with so many other things in life, both are true. There isn’t a single answer that suits everyone, and in actuality it’s not so much a matter of making choices before the fact about how we’re going to make things happen as how things appear, looking back on how they’ve happened to us along the way.
Work can also be a form of what Steven Pressfield calls Resistance—something that feels worthwhile, important, and necessary, but that’s really a one-step-forward, two-steps-backwards ratchet holding us back in our creative journey—and even moreso these days with the prevalence of modern productivity tools like Asana, Monday, Trello, and Basecamp. Let’s face it, remote work would hardly be possible without these nifty online systems, but they’re also a way to make completing arbitrary tasks seem like fun. Tasks, subtasks, milestones, and due dates multiply like small mammals in springtime, and each comes attached to a cute little checkbox that provokes a rewarding squirt of dopamine. Work was already addictive in terms of its delivery of money in exchange for bits of our soul, but now we’ve gamified task completion into yet another slot machine that over-delivers short-term satisfaction for the Scarcity Brain while keeping the odds squarely in favor of the house.
Our long-standing story about work is that it’s the path to the American Dream, but what work wants is for us to work more, not to get ahead, let alone break free. Work offers the promise of identity, but most mainstream professions require us to subsume much of our individuality to earn the flag of belonging. Given that until relatively recently ‘work’ as a socio-economic construct was mostly the cultural province of men, I don’t think it’s coincidental that work so closely mirrors the hegemonic nature of traditional masculinity. Most of us still carry many generations of accumulated learning that to be a man at all, we have to conform to what it means to be a Man, thus giving up our individual expression thereof. Work—and “manhood” as most often understood—offer extrinsic definitions or layers of identity at the expense of the intrinsic self. Perhaps the more modern model of a multitude of masculinities can also be seen as a more entrepreneurial way to approach identity. DYOR people—DIY, and FIRE—LFG!
Returning to work has me experiencing again firsthand how much work does contribute to my sense of being someone in the world—and also what it's like to have part of my brain consumed by work. Getting invited into someone else’s business is a deep honor, and something that I didn’t hesitate to say yes to—and it’s also giving me a fresh look at the real value of my time. I’ve loved the process of turning myself into enough of a writer over the past few years to make that part of who I am—and it’s impossible to deny that having a bit more cash in my pocket also makes me feel more engaged, and more whole.
As much as I’ve always been an entrepreneur, and proud of it, I’ve struggled with the way that our culture speaks out of both sides of the mouth about work, money, and entrepreneurship. Even now I always make a point of carefully explaining that I sold my business, but it wasn’t a big business, and certainly not a Silicon-Valley-type megabucks tech business. It was an old-fashioned American small business, but even that clear fact doesn’t entirely inoculate me from being someone who made it… and isn’t working quite hard enough!
For all the ways there are supposed to be to win here in America, we sure cook up a lot of ways to lose. Don’t earn enough—you lose. Earn too much, and, surprise!—you lose. Let me just say it right here: earning money isn’t a bad thing, and I feel like proof enough that one perfectly fine way to escape the rat race is from the inside. I’d rather co-opt the levers of power than retreat, only to spend my time chewing the wires of the cage.
Of course, I’m not driven to “work.” Fuck that.
I’m driven to live as much, and as close to how I feel as my heart will allow. It’s been a challenge, and it gets more interesting every year. That’s what keeps me earning my bread.
The “Work and Money” Series
See also our first series on Fatherhood, and our second on Recovery.
References and Further Reading
Nicoyan diet — Secrets of the Blue Zones (Netflix)
Barbell strategy — Nassim Taleb, Antifragile
Discipine — Bowen Dwelle, How I confused "discipline" with getting told what to do
Myth of the starving artist — Chase Jarvis: Creativity Is Our Birthright on the Rich Roll podcast
Resistance — Steven Pressfield, The War of Art
Search for purpose — Bowen Dwelle, The False Grail
Dao / The Path — Christine Gross-Loh & Michael Puett, The Path: What Chinese Philosophers Can Teach Us about the Good Life
Growth — Bowen Dwelle, Let’s Kill “Content” and Reclaim Growth
Addiction and the dopamine cycle — Michael Easter, Scarcity Brain
Hegemonic masculinity — David Buchbinder, Studying Men and Masculinities
Entrepreneurship — Bowen Dwelle, Early days in the advertising-industrial complex, and why nobody wants to pay for writing.
My own book: An Ordinary Disaster
Last year, I serialized chapters from my memoir as a work in progress here on Substack. I completed the manuscript in the early fall, and it’s been resting here on my writing desk since then. My current take is that the introduction that I wrote after having completed the text promises a bit more than the book delivers; either way, (of course) I have a fair bit of editing to do. Don’t worry—I’m not gonna let it sit for too much longer. One way or another, the book will be out this year.
Speaking of books, check out The Crew, recently published by my friend Michael Mohr.
Substack Writer meetup in SF, April 22
We held the first Bay Area Substack Writer Meetup back in December and it was a great success, with nearly 30 writers mixing it up live, in person! I’m hosting another one on April 22 — please join if you are in the area!
Sign up here → https://lu.ma/2mfnfscb
Questions for you
What’s your own relationship with work and money?
How have you found jobs—more by looking, or opportunistically?
What do you think about being a “starving artist”?
How much does your work contribute to your sense of who you are?
What’s been new and interesting for you in the first part of 2024?
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I really like the point about the number of ways we’ve cooked up to lose. We all think we need to be exceptional, the .01% outcome, and sometimes it’s a really seditious act to just say, “I’m going to win by not pursuing that.”
Great thoughts and reflections. I’m so happy that you’ve found something comfortable and that works for you. You sound happier even through the words on the screen. And as Dee said, I’m with you on dropping the ego and only hanging with people who don’t need to prove themselves. Although for a long time I needed to prove myself.
Especially appreciate this point: "In America, we’re expected to craft a path entirely of our own making, with the assumption that not only is this the right and best way to achieve our own happiness and fulfillment, but also that of society as a whole.... It doesn’t always have to be about me."
I was thinking about this and couldn't find a way to work it into my essay, but the seemingly limitless possibilities for professional success in America can be paralyzing. What looks like freedom -- chart your own path -- can just be exhausting if you don't have a bright idea for that path. This is not to get into the invisible barriers that give the lie to the American Dream, but I think about the incredible stress associated with figuring out your next move as an American. It's a mixed blessing, because you wouldn't want to have your path chosen FOR you, the way it was for medieval peasants, but there is also freedom in a kind of communal definition of purpose, like you experienced with your friend's invitation. It's not up to you to figure it all out. There is a need, someone asked for your help, and you can give it. I think it used to be more like that.
Case in point: in my hometown, if you went to college, you were able to get a job, no questions asked, with the Forest Service. This was a government program designed to bring rural kids home for the summer, and it worked. Zero stress involved. When I tried to send some of my own students on a similar path, the whole game had changed. Now there was a database that you had to enter your information in, even if you had a personal contact at one of the national forests (as I did). Ostensibly, this was to be more inclusive, and I can understand resisting the old boy network. And yet it also seemed to needlessly complicate things. There weren't going to be impoverished urban kids applying to jobs in rural Montana. It seemed that a personal recommendation ought to open some doors, simplify things. I actually think this is how most business insiders still work -- on referrals, rather than cold applications or queries -- and it can be maddening if you're on the outside looking in. But why not leverage personal networks if you can? It's one way to avoid staring blankly at your future with no idea what you should be.