Question: "How do I improve my humor writing?"

A young person asks. I answer.

This week, a young person in the first blush of her career asked, “How do I improve my humor writing? I will send you a Cuban cigar.”

Because bribes work, I spoke to her at length. As my answer was predictably detailed, and probably somewhat surprising—and in the hopes that each one of YOU will send me a Cuban cigar—I will share it here.

Boilvar Belicoso Finos if you can, but I’m not prepared to be snotty about it.

Let’s begin with the proper context. This is not advice to become successful. If you want to have a big Twitter account, go find another big Twitter account and write like that. If you want to be a TV writer, go watch a bunch of Black-ish or Big Mouth or whatever, and write like that. If you want to get into The New Yorker’s Daily Shouts, same thing.

It is not difficult to do these things; it is not easy, but unless you’re uncommonly unlucky (and that does happen), all it takes is focus, a decent ear, and perseverance. That kind of writing is commerce, and there’s nothing wrong with that (and a lot right with it). But, as many times as I’ve wished it were, commerce is not my beat. My beat is art, for better or worse.

The advice below is my best guess at how to get good at the art of humor writing. What “good” means, is up to you. “Good” may not be successful, and it may not be recognized. But it will be, according to your own definition, “good,” and that’s a worthy pursuit.

• • •

Obviously, you’re reading a lot of stuff, whatever kind of stuff you like. Maybe you’re taking classes, or in a writer’s group—I was personally a bit wary of both of those things. A class is often only as good as your teacher, and a writer’s group, if you get a bad bunch, could move you in exactly the wrong direction.

First, the obvious answer: fill notebooks. When I was a young writer I used to buy a college-ruled, spiral-bound notebook for about a buck. Then I’d carry it with me, and write it full over the next three months. I still do this when I’m visiting my parents in Michigan. For me, there is something magical about a fresh, new 99-cent spiral-bound notebook with a unicorn on it.

Proust had his madeleine, I have spiral notebooks from Barney’s Market in New Buffalo, Michigan.

Later, I carried a Moleskine in my back pocket, because I found that I didn’t have to work out ideas at length. I could just write “Orson Welles and Che Guevara,” and write it up when I got home. These days I don’t carry a notebook at all; I might jot something into Notes on my phone, but generally whenever I sit down at the computer, the dog comes.

Anyway, you want this notebook to be cheap, and a little shabby, and a place for your youngest, most free self to come out to play. Think of it like sneaking off to your old elementary school playground at midnight, and fucking around on the swings, the slide, the monkey bars. Throwing doughnut holes at passing cars and running away giggling when the cops show up.

A comedy writer’s notebook should be full of false starts, doomed notions, and things you’d never say in public; in this most audience-determined form of writing, your notebook is only for you. And the act of writing it by hand is important, too. For me, handwriting is hard, my hand cramps, the pen smears, every word takes a bit of subtle effort…which makes me really focus on the idea, if only for an extra moment.

Typing isn’t merely too easy, it also skips a step—it turns a raw idea into something that looks finished. Writing out by hand means that if something has promise, you have to flesh it out further by typing it; and that step invariably allows me to deepen the idea and play with it.

Do I still have any of these old notebooks? No, and I don’t mind a bit, because I have the books and articles that were born in them. My notebooks were disposable, and that was the point. Even the thought of keeping them would’ve tightened me up considerably.

• • •

Then, there is the common answer to this question, which is, “If you want to get good, write a Substack” (or blog, or Tweet, or whatever). This is actually a lousy idea, for several reasons.

A beginning humorist is pliable. They have some ability, and a vague notion of wanting to make strangers laugh, and they are exquisitely sensitive to praise and criticism.

So praise for, or criticism of, the wrong things, that is, feedback from the wrong audience, can actually ruin a young writer. Most—and I mean 90%—of all the humor writing I read on the internet sounds the same. It is the same types of premises on the same types of topics, delivered in a similar voice. Even when it’s well done, even when it’s popular, there’s nothing special there.

If there is one thing killing humorous prose, it’s this infernal sameness. Some of this problem stems from aspiring humorists reading this stuff and mimicking it…but I’m convinced that some of it comes from praise from audiences with lousy taste.

Unless you’re already formed as a writer, and experienced enough to make a standard topic your own, writing humor about dogs or cats or changing your kid’s diapers, or writing in the voice of The Onion or McSweeney’s, is dangerous. Especially if you’re gifted—if comic writing comes naturally to you—the easy praise you’ll get for doing the easy stuff, might keep you from becoming really great.

I still remember a quite uncomfortable conversation with a fellow who ran a big humor site on Medium. He was justifiably proud of the traffic it generated, and did not understand why I didn’t want to publish a bunch of it in Bystander. How could I explain that “good” is fine for pixels, but paper requires something more? Paper is finite and physical—it insists on a kind of discipline alien to the web, and rewards it, one hopes, with a kind of permanence. Whatever else we can say, The American Bystander will lurk quietly in the bowels of nuke-insulated libraries at Yale and Harvard, long after the founders of Medium have fucked off to Tahiti and every page on their site has been rendered unreadable by some bit of new code in the latest internet browsers.

Particularly as a developing humorist, you want praise from the right people. Who are the right people? Often, people in the business you admire. For me, that was Mark O’Donnell, Ian Frazier, Sean Kelly, Harvey Kurtzman. Reach out to professionals; often, they will answer (especially if you bribe them).

But they don’t have to be big names. Mostly, you want people with good senses of humor; people who read carefully and have active minds—who really engage with your work; people who are like you in some fundamental way or, if that’s impossible, seem to understand what you are trying to do. Find people with good taste, and write for them. My Uncle David. My friends Jon or Dave or Josh. When they said something was good, I could trust it.

In a world of vast, vast content oversupply—especially of light, voicey writing about daily life—you must force yourself to go beyond. Unlike the late Eighties and early Nineties, you won’t have a cadre of hardassed, every-square-inch-is-precious editors holding you to an impossible standard; I hated them then, but I appreciate them now, precisely because I write Benchleyesque humor as easy as breathing. Daniel Menaker never admitted that he’d made a mistake not scooping Jon and I for The New Yorker, even after I was literally running the finest literary humor magazine of the 21st Century, and God bless him for it. Dan had his opinion, goddamn it, and nothing hones a worthy talent more than an old man in the way.

(I surely have played that role for many. I’m truly sorry, and you’re truly welcome. :-)

Social media will be satisfied with good. Most writers will be satisfied with that, too, especially if it comes with a little money. I think that if you write humor at all, you should try to be great. Whatever that means to you.

For me, that meant Robert Benchley, Doug Kenney, Alan Coren, Jean Shepherd. From the age of 12 on, I hunted those guys. Stalked them. Maybe I got them, maybe I didn’t—that’s not for me to say. The point is, make your own pantheon, and force your way into it.

• • •

None of this is my secret trick, which will by now be obvious: read old stuff and steal everything you can. Most funny writers are not scholars about it, so this is an advantage you can exploit. Go dig into old collections of short humor, see what you can repurpose for your own work.

Here are some ones to start with: Laughing Matters by Gene Shalit; Russell Baker’s Book of American Humor; The Big Book of New American Humor; A Subtreasury of American Humor, by Katharine and E.B. White.

Most of these pieces will feel dusty to you, out-of-date. Good. That means there’s sufficient distance between those styles and approaches, and the ones current today. That is: stuff you can steal. Read contemporary stuff for pleasure; read old stuff to larceny.

Read the work forensically; what is the writer trying to do, and how do they use the facets of writing to achieve it? Language and voice, sure, but also sentence length, piece structure, punctuation. Are they warm or cool? Friendly or prickly? Are you a co-conspirator, or a detached viewer?

If you do this too much, your work may start to feel a little out-of-step with the current era. Don’t worry—just keep writing, this is only temporary. Eventually you will metabolize what you’ve read, and it will give you a big bag of tricks very different than your competition with brains full of Twitter memes and Rick and Morty. They may get the jobs, but you will be on your way to becoming yourself.

I remember one day in 2001, when one of my favorite young writers from The Yale Record came up and said, “Have you ever read Fred Allen?” I had to admit that while I knew the name, and that he was a popular radio host and columnist in the 1940s and 50s, I’d never read the guy. “You should check him out! I’ve been carrying around a book of his letters for a week!”

Tellingly, this person did not go into professional comedy, though if he had, he would’ve had a very fine career at the highest levels. He intuited, quite correctly, that professional comedy is not what it once was. As it has become a respectable alternative to law school, it has attracted more and more of those kinds of brains, very smart and very ambitious, but very conventional. The George Meyer’s of today—or the Brian McConnachie’s, or Doug Kenney’s—will more easily be found in a tech-related field, something like video game design (where my young friend ended up).

Which leads me to my final point, on this Friday evening as this morning’s acupuncture treatment ebbs away and sleep is calling: perhaps the most important facet of improving your comedy writing may be getting so good you realize it’s not for you, at least not professionally. That’s not a failure. In fact, it can be the deepest kind of success. The goal is to have the kind of life you wish to have, and to look back on it with great satisfaction…as you smoke a fine Cuban cigar (hint, hint).

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The notoriously clean-living MICHAEL GERBER has, as a goal of middle-age, decided to cultivate a few harmless vices—of which advice is most assuredly one. You can write him for more of it at Publisher@americanbystander.org.