Sam Holstein

What I Want To Write Doesn’t Make Money on Medium

My favorite writer is Alan Watts. Watts is considered a philosopher or a theologian before he’s considered a writer, but he’s only able to communicate penetrating insights about the nature of existence thanks to his superb writing skills. He uses his ability to tell a story to tell stories which illustrate deeper truths that direct, literal sentences could never communicate. It’s a terribly difficult skill to master, and the skill I most want to master in this world.

The problem is that Watts’ style of writing wouldn’t do well on Medium, and Medium is how I make money.

What’s popular on Medium is a highly stylized yet casual style of writing about traditionally taboo topics like sexuality, prejudice, and mental illness, a la Shannon Ashley or Gillian Sisley. In my opinion, it’s a hell of a lot easier to write headlines for this style of writing. Ashley has an article with the headline I Had A Threesome And It Was Awkward AF. Clicky headline, clicky article, no problem there.

Not so with Watts. My favorite essay by Watts, possibly my favorite essay by anyone, is titled The Finger and The Moon. It’s about how all religious systems are merely the finger, and the real object of religious systems is to get you to look past the finger and at the moon. Once you see the moon, you can drop the finger.

It’s a beautiful piece of writing, but if it were posted on Medium under a pseudonym with no followers, I don’t think it would get any traction. Why? Because that headline is vague as fuck. It’s exactly the kind of headline I scroll past, rolling my eyes and thinking “It’s probably some half-edited anecdote about a night the writer got drunk or something,” not anything worth reading. The reason we all make this assumption is in the internet age, writers who write well tend to also give their pieces clear headlines, like Surrounding Yourself With Positive People Isn’t Always The Best Choice or Experimenting With Poetry Makes Me A Better Writer.

Watts excellent philosophical articles have opened my eyes to so much about the nature of existence, but I find it virtually impossible to write a clicky headline for this kind of work. I certainly can’t for mine. I have written countless pieces with winding narratives — most of which I don’t publish because I am totally unable to figure out how to title and sell them.

From a business point of view, this is a bad sign. An entrepreneur with a good product he totally can’t market is typically actually a bad entrepreneur because he’s created something no one wants.

But I know some people want this product, because Alan Watts books still sell and David Foster Wallace’s most popular article ever is called Consider The Lobster, for fuck’s sake. That headline would make Neil Patel’s toes curl, yet it’s a landmark in literary history.

There is one thing I can see these philosophers all have in common.

They spent the better part of a decade cutting their teeth.

Wallace, Watts, Ryan Holiday, and even John Gorman all spent countless hours writing stuff that was mostly garbage before even beginning to get anywhere near something resembling philosophical.

Does this mean I have to spend years cutting my teeth writing unremarkable garbage before becoming the kind of writer I really want to be?

It looks like the answer is a qualified yes.

I’m qualifying that yes because I don’t believe in the traditional ‘write every day’ advice writers give each other.

I used to play golf competitively. I had been competing for eight years and was being circled by Division I recruiters when I quit. One of the most important lessons of golf is that practice does not make perfect, practice makes permanent. If you go to the driving range and practice a terrible, hinky swing, you’ll just make a habit of your hinky swing. It’s literally worseto go to the range and practice a bad swing than it is to not practice at all.

I’m no competitive writer, but I suspect writing is the same way. If if I wake up every day and write clicky drivel, all that will happen is I’ll get real good at writing clicky drivel. To write philosophical narratives, I have to practice writing philosophical narratives.

Which is a problem. Nobody on Medium pays you for that shit, so I’ve avoided publishing anything like that thus far.

But it’s time for me to put that fear away. After all, nobody becomes a writer for the money.