On Not Writing

“A man may write at any time if he set himself doggedly to it.”- Samuel Johnson

You know you’re something of a writer if you’ll do anything to avoid writing. I’ve waged a lifelong battle against the craft going back to childhood. In one of my earliest literary memories, I’m seated in my room at a little desk writing away about some fantastical Hobbit-like creature. But after a few minutes, I become so worried that someone will see me writing that I get up and lock the door, a forbidden act in the Boyle household. What if someone found out that I was … a writer? Were my stories worth preserving? And worse, what would happen if someone actually read my writings?

Even as a child, the act of writing felt embarrassing and shameful; something that I should hide from the outside world or stop doing altogether. That a child can intuit the artist’s curse so early in life is an indication that it’s a cultural condition, passed down by generations that ostracized poets and philosophers who could have had more productive jobs as salesmen.

The simultaneous indulgence and danger of writing that mires the fortunes of many artists is well-documented, even among our literary heroes. It’s confirmed by the thousands of books that claim to help writers overcome two distinct fears, which lead to the same outcomes: procrastination, half-written pieces and other forms of “I’m thinking of writing a screenplay…” that end with mere conversation.  From “The Artist’s Way” to the more political “Persecution and the Art of Writing,” the two poles of artistic repression—neurotic self-consciousness and the genuine fear of persecution—are always enough for us to put down our pens and say “perhaps I should vacuum the house instead.”

But I never completely rid myself of writing. In my most productive moments, I created valid excuses to do it. During my 20s, “not starving” became the solid reason to suffer embarrassment and/or persecution for the publication of my thoughts. And let’s be honest, embarrassment was a more common worry. Among my first projects as a cub reporter was writing blurbs about the annual winners of The Washington Post’s Peeps Diorama contest. Here’s my all-time favorite “Zero Peep Thirty.”

I suspect I became a reporter because writing for money seemed far less shameful than writing for fun. I joined The Washington Post at age 24, and my marriage with The Post made me legitimate.  It was the first time I felt free of shame, but also the first time I felt fully conscious of the danger writing poses. The culture desk at any publication can lead one straight into a minefield. I took great pride in writing for The Washington Post Style section, the former bastion of New Journalism that allowed reporters to indulge themselves with linguistic experimentation that put them closer to the edge of what one shouldn’t say. Or perhaps just closer to an editor’s ire: I benefitted greatly from budget cuts-turned-copy editor firings that allowed me to leave overwrought flourish in my copy. Behold, 5000 words on Vanna White, sweaty men and the origins of big box retail!

Tom Wolfe got his start at the Style desk, and as one of my literary heroes, I often reminded myself that sitting near his desk was both a privilege and a burden. He seemed to have no shame alliterating his thoughts for a broad and game audience that gave him leeway for mistakes. Somehow, I too needed to find the courage to dance along the dangerous line of telling the truth without causing too much offense or losing my job.

The irony of this fear is that I was set to lose my job due to a broken business model long before I would lose my job because of my dangerous prose. I left The Post to go west for a better life, and in the last few years, have had neither the excuse nor courage to write anything of value.

Which brings me to Substack, a product that has been called many things by many tech people, except what it is for writers: a shame reduction tool, a valid reason to write, and a movement that allows writers with creative phobias to overcome the self-consciousness that stops us halfway down the page. It also allows writers to approach danger and self-consciousness head on. Unlike anything I’ve used before, it has productized the writer’s experience, encouraging the timid to write on deadline despite lacking the editor shouting over your shoulder.

I’d also like to think of it as a place to confront danger—and to learn, convincingly—that your readers want you to dance at the edge of precarious ideas. And as a reward for embracing the fear of persecution? Money! Potentially much more of it than most writers make elsewhere. Though this former reporter will not be monetizing her newsletter, it’s the first product I’ve wanted to use to keep me honest about my irrational fear of writing. And, perhaps, I might finally overcome it.


So welcome to The Rambler, named after my favorite work by Samuel Johnson, one of the most prolific newsletter writers in history. Johnson had no time for people who didn’t write, nor did he have the time to not write, which is how he became so talented at the craft and left us with enduring wit and works. He wrote without self-consciousness and was worthy of the cancellation that he would have experienced today.  

In the vein of Johnson, my dispatches will be both short and long, somewhat irregular and in dire need of editing. I expect most of them will be about technology, culture and philosophy, but allow me to meditate on the obscure once in a while, in honor of Mr. Johnson’s cavernous mind. I’m allowing my professional writer friends to instill the fear of deadlines in me, but there’s one place, dear reader, where you can help: affording me the freedom to make arguments I can’t make elsewhere, knowing full well they could offend and cross the invisible lines I don’t see. I expect most of these ideas to be half-baked and not worthy of your outrage, but have mercy should I overstep. Consider this my blanket mea culpa.

There’s no greater pain or joy than publishing one’s mind. And there’s no greater burden than a smart audience that anticipates your work and exposes its limitations.

Thank you for embarking on this experiment with me.

-K. Boyle

(Note: I have a day job at a venture capital firm. Absolutely nothing I write should be taken with any seriousness whatsoever, and it DEFINITELY does not represent the views of my partners or the good people who employ me. The Rambler is not intended as an offer of securities or as investment advice or investment recommendations of any kind. Also, nothing I say here is indicative of any past, present, or future investment or business activity of the venture capital firm with which I am employed. If you wish to communicate with me about anything connected with said venture capital firm, please contact me there.)