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Writers are Losers

5 min

It's easier than ever for writers to earn good money, but don't get it twisted: You still must dare to be a loser.

We live in a strange era where words and dreams and realities constantly crisscross in befuddling ways.

Take the concept of writing.

Historically, choosing to be a "writer" has generally meant choosing to be a loser.

That’s pretty much the bargain. One takes freedom and exercises nonconforming self-expression, but in exchange, one gives up just about every reliable road to money and status.

Obviously, some number of writers in every time and place strike it rich, but such a result has always been so statistically unlikely that in virtually no case could it ever have been a reasonable expectation. Thus, even most of those writers from previous eras who struck gold nonetheless crossed through, at some point, the psychological act of choosing to be a loser.

Edgar Allen Poe could have had a successful life working for the family business, but he chose to be a writer. He was never able to support his family, got into binge drinking, became deranged, and died at 40.

Ernest Hemingway, despite his romantic masculine image having aged rather favorably, ended up a loser. His mundane failures of character are well known and need not be repeated, but Burroughs has an interesting take on Hemingway. In his essay "Creative Reading," published in The Adding Machine, Burroughs writes:

“Style can become a limitation and a burden. Hemingway was a prisoner of his style. No one can talk like the characters in Hemingway except the characters in Hemingway. His style in the widest sense finally killed him. 'I’d shoot down my own mother,'' he wrote in a letter to a friend, 'if she was a mallard and I could lead her sweet and clean with no. 4 load.'"

Hemingway chose to be a writer, even if it meant killing his mother to obtain a good sentence. As Burroughs notes, Hemingway sold out to Hollywood (by his own admission), his final works were lame commercial projects that betrayed his original spirit, and he died a cowardly fraud at his own hand.

Go back further in time and my point is even more obvious. In 18th- and 19th-century Europe, writers often lived in garrets. This fact is not always understood: Garrets were tiny unfinished attics at the top of buildings. It was closer to what we would call "homeless" than to what we would call "renting an attic." Don't imagine "staying in someone's attic," imagine sleeping on a roof with rats, with just a sleeping bag and little rain cover.

Victor Hugo, Knut Hamsun, Chateaubriand, Balzac, just to name a few, all spent some time living in garrets. They chose to be homeless because they chose to be writers. We know their names today so we find it difficult to process, but they chose to be losers. Each one had hundreds of contemporaries who also chose to be losers, but those contemporaries really became losers. Since they chose to be losers and became losers, we never hear about them. So again we underweight this invisible evidence—that choosing to be a writer essentially means choosing to be a loser.

It's always been like this, and it still is like this. I wrote about this recently in The Struggle of the Independent Scholar.

The Struggle of the Independent Scholar
“I want to leave academia, but I need money.”

But today, a certain number of people have figured out semi-reproducible ways to get rich and famous by writing. It's still very rare, statistically, but it's less rare per capita. The other big difference now is that the path is permissionless. Winning the approval of some gatekeeper was formerly a hard requirement, which would often require as much effort and attention as the work itself. So on one level, there's never been a better time to be a writer.

On another level, the new situation is more confusing than anything else, and it might even have a net-negative effect on overall writerly productivity.

Because there are now several dozens of self-made writers who figured out how to get rich and famous, it now looks like choosing to be a writer does not necessarily mean choosing to be a loser.

But in fact, the psychological requirement has not changed. If you set out to be a writer because you want to be rich and famous, you're almost guaranteed to fail—you'll either become rich and famous, with your writing as a shallow pretext, or you'll fail to stick with writing when you realize that writing is for losers. If you stick with writing after you realize it's for losers, you are delivered a unique, secret raffle ticket reserved for the select few in this dubious class. But you're still a loser! And if you say your chances are good for that lottery, you're probably an insufferable dork as well. Of course, privately, you may know with certainty that your chances are high—destined, even. But that's not really an empirical prediction, that's more like faith.

Moreover, looking at the rich and famous writers of today can sometimes give one the impression that now there is only one single category of writing success. In fact, members of that category often pay severe costs in other dimensions, and it's not at all obvious they've found the global maximum or final ideal.

We know it's not the only equilibrium. It's a matter of rationally decomposing the necessary moving parts, and coldly calculating whether one can live a different kind of writing life and make decent money, perhaps with unique advantages over more visible models.

I'm pretty sure I've carved out a unique equilibrium myself, and the reason I'm pretty sure is that I still can't tell if I'm poor or rich. Everyone else I know who I would consider a successful independent writer is either much richer than me, or else it's not a professional pursuit for them (i.e. not their main source of income). I'm the only person I know who is a full-time writer/"creator" and is also just a member of the hard-working middle class (i.e., there's still a fairly linear relationship between my labor and my income.) It's very weird and psychologically fraught. I compare myself to my successful independent writer friends and I feel like I am poor and struggling. I compare myself to typical professors or traditional book authors and I feel pretty rich.. The honest truth is that I don't really identify as either. I don't really know which view is more correct. I move around the world with a genuine feeling of classlessness. Not from any enlightened consciousness, but purely from sociological disorientation. The disorientation is caused by the absence of a single peer group. In its place, multiple fragmented peer groups that do not recognize each other. The independent man today has no single yardstick recognized by all of his various, partial peer groups.

But I'm as free as they come. I'm undeniably on my own path and I'm paying the bills. I've really optimized so hard for the most open-ended freedom possible (probably too much so, I'm starting to think). Of course, this could be pure cope, a way to rationalize why I'm not more successful. Perhaps I'm a vapid writer and I'm bad at business. I'm at peace with the possibility.

Maybe I am a loser. But I'm definitely a free man, and I try my best to write what seems true and important.

However my future pans out, I would still take this trade any day of the week.


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