Freelancing Ain’t All Wine and Roses

My recent hiatus from freelance writing culminated in an existential crisis that I now think was actually about money.  It’s interesting how money—getting it, keeping it, losing it, worrying about it, hating it, enduring its fraught passage through our lives—often seems to be the underlying rule and mean in situations we first thought were about love or fate or right choices.  Life might not always be about money.  But lately I’ve had a hard time seeing when it isn’t.

The realization hit me while I was cutting banana trees for my neighbor.  Every freelancer encounters dry spells and every dry spell brings angst, a spate of dreadful job applications, and self-imposed austerity measures which help far less than you think they should.  In the middle of that, volunteering to prune banana trees should be therapeutic.  It some ways, it is.

In others, it only drives the nail of precarity deeper into your skull: what am I doing when I should be looking for a new paying project?  What am I doing volunteering for anything?  What is my age?  What choices have I made that put me here?  How much am I to blame?  How do I set this worry and anger aside so I can get back on the hustle?  Will this petty opportunity cost return as top ramen and hot dogs, holy T-shirts and rent anxiety?  Where will I be this time next year?  And will I have all the teeth I have now?

These are questions freelancers never want to ask but inevitably do.  This is the fear that only those with money have the luxury of being generous.  This is how your world gets smaller, how you end up optimizing every moment for work instead of living a life.  So I pruned my neighbor’s banana trees with a Ryobi P519 Reciprocating Sawzall in high tropical humidity and tried not to wallow.

Heavy yard work can be good for the soul, especially work that involves razor-sharp power tools.  Still, through the whole day, my inner existential calculator-self-critic-time-clock was hard at work dredging up a range of facts, assumptions, and figures that all led to the same thought: kindness is stupid when you’re broke.

Unfortunately, by that reasoning, so is art, writing, music, libraries, museums, public broadcasting, kite flying, junior college, cooking, learning languages, community theater, and any other thing that brings joy and meaning to someone whose emotional life isn’t completely constrained by making a buck.  It’s what the ladies’ self-help success guru, Penelope Trunk, used to say when she’d argue that graduate school in the humanities should require a trust fund. In her reductive materialism, culture and self-expression are supposed to come with a price tag like everything else.  And if you can’t afford it, well, get back in your cage.

The commodification of kindness and creativity is something I hate as much as anything I’ve ever hated, a set of beliefs about the world that I vehemently reject.  Of course, I do.  I’m a former English teacher.  I have a hard-earned PhD in the subject.  I write books.  And those skills also feed me as a freelancer, even if the life I lead is a bit like that of a low-stakes professional gambler.  Nevertheless, poverty sucks.

I dislike large parts of capitalism, at least, the post-industrial variety carried into my generation by the Boomers.  But I do think my fellow Gen-Xers doth protest a bit much.  My parents’ post-WWII generation did the best they could and, in many cases, that was pretty great.  The people around me, born in the early 1970s, who came of age in the late 80s and early 90s, also did their level best.  Put into the widest global perspective for our time, we had it pretty good.  And I believe in hard work.

Everyone I knew growing up in lower-middle-class southern California shared that belief and mostly survived.  Many of us, especially the arts and humanities types, went into debt and paid an enormous psychological price to do the things we felt called to do.  And we seemed to enjoy a much smaller return on those efforts than that of previous generations.  But we still shut our mouths and tried to make a living.  I guess we’re still trying.

But millennials?  Gen-Z?  I’m not sure I know what form of life they are.  Terms like “self-entitlement,” “performative victimhood,” and “Twitter mob” do come to mind.  When I interact with them socially or read about them as a group, I come away feeling like I’ve encountered an undulant mass of mewling, protoplasmic, always-online identity cosplayers.

I know that this is not true and that sweeping generalizations are inherently invalid.  And I suspect generations largely aggregate into the same qualities and quantities that have always existed; though, I’d be hard pressed to come up with an earlier analogue for Instagram catgirls,  and gig sensitivity readers. These generations are tomorrow’s freelance writers and Uber drivers. And there will be so many more of them.

At the same time, I wonder if people hitting the workforce now, in their 20s and 30s, with crippling debt, a lingering pandemic, and the hottest temperatures in recorded history, have the same inner fallout when they can’t find work.  I wonder whether they even want to work the way I have, the way I still work?  Do they doubt themselves, even after decades of professional experience?  Do the former English majors sometimes reach a point where they swear they’re giving up the thankless writing life (because, let’s face it, the last thing the world needs is another writer) but find themselves coming back to it again and again like an addiction?

I have no doubt that some of them will come around to my way of thinking while cutting banana trees and flirting with heat stroke: maybe what the world needs is not what I need.  Maybe a writer’s job is not to be respectable and flush, but to write and avoid getting flushed. Maybe no matter how many trees I prune, I know I’ll be heading back to the writing desk sooner or later, dental plan or not.  If not today, then tomorrow.  If not tomorrow, then next week.  If not next week, then never.  Because in this game, there is no victory scenario, no rest, no stopping until they put me in the ground.