Advice to the Young Humor Writer

My advice to the young humor writer who wants to improve at humor writing.

I sometimes get asked by young humor writers for advice. I pretty much tell them all the same thing: I don’t know anything. Stop bothering me. But they pester me until I relent and give them something resembling advice. In the interest of saving myself time, I’m putting it all down here for future reference.

Dear Youngster,

The thing that’s helped me the most as a writer is asking the question–and please pardon my language– “Would anyone give a shit about this?” If I can honestly say that people would, I write it. If I can’t think of a reason anyone in the world would care, I don’t write it.

Now, “Would anyone give a shit about this?” sounds like common sense advice.

But let’s break it down.

“Would anyone…”
This means you should consider the audience. Does your idea have an audience? Who is the audience? Will they agree? Disagree? Both are good. Book authors, screenwriters, columnists – they all know their audiences. If you don’t know who yours is, think about who you would want to be your audience and what would be interesting to them.

I know that writers often say they “write purely for myself,” but those authors generally have gigantic followings already and live in large writer mansions by the time people ask them for advice. Of course they write for themselves. Now. They didn’t always. The liars.

“…give a shit…”
What is your intended audience not getting enough of? What would they enjoy? What would they share with each other? Be brutally honest when you answer these questions.

Because YOU wrote it doesn’t mean the heavens will rain page views down on your 8,000-word take about how lame the Oscars were this year. Don’t hope or expect an audience to react BECAUSE IT’S YOU writing it, and don’t become disappointed if no one reacts or likes it. Negative feedback is the best feedback of all.

“…about this?”
“This” is your work, and it has to be good. It should be funny. It should include the unexpected. It should be well-written with perfect grammar and spelling. “This” should make you laugh when you read it or think about it. If it’s not funny to you, why would it be funny to anyone else?

Have you ever seen a stand-up comedian bomb? It’s horrible to watch. It makes me want to hide under the table until it’s over. Nine times out of ten it’s because they’re telling jokes even they don’t think are funny. Enthusiasm about your own work is infectious, provided it’s good work. If it’s not good, enthusiasm wanders into the realm of derangement, which is also funny but the target of your humor becomes your own dignity. There are better, juicier targets out there because as a wannabe humor writer you are most likely bereft of dignity.

I say this all because, having browsed through your website, I see you writing a lot for yourself but not with a reader in mind.

You obviously have things to say about the world, and the fact that you reached out means this is more than a passing interest to you.

So if you’re serious, here’s what I would advise:

1. Read all of the humor writing you can, online and in books. Look at what these authors are doing structurally–not just the funny lines, but how the humor is built and constructed. Deconstruct until you understand all of the invisible writer tricks that allow writers to be so clever. Then look at what they choose to write about. Are they talking about things they think, or are they going out and experiencing life and telling interesting stories that happened to them? They’re probably not doing much of the first and more of the rest. The more active choices you make in life and the more you leave your desk and do things and then return to write, the higher the ceiling for your comedy.


2. Write all the time. Even if you don’t publish it, write. When something strikes you as truly funny, build off that idea. I have notebooks and Word docs filled with terrible, terrible ideas that no one — thank God — will ever see. But I needed to get all of those crummy ideas down on paper before the good ones came out. I still do a lot of crummy writing. But the more writing you do, the faster you can spot when it’s crummy. Here’s a screen-grab from my Word doc of rejected ideas:


This idea is mildly humorous, but it would need to make fun of celebrities, not people living in their car, who are a group of people who don’t deserve ridicule. Does the world need another article bashing celebs? Not really. So into the reject pile it went.

3. Cultivate an audience. Make 10 hardcore fans. Then 50. Then 100. Go where the people are – Facebook, Twitter, Tumblr, etc. I even publish on LinkedIn, that thing everyone with a job knows they’re supposed to be on but just can’t bring themselves to join. I crank out a quick column, and I pick up new followers and grow my audience.

4. Be as real as possible in your writing. I enjoy McSweeney’s and The Onion, but for the individual blogger there is more humor in reality than in exaggeration. Anyone can comment on pop culture or write a fake news story, but you are the only one who can tell your stories and who cares about the specific things you care about in the way that you do. The things that make you unlike anyone else on earth are your advantages as a writer.

Think of a Venn diagram – where your interests and an audience’s interests overlap, that’s your sweet spot.

For my American readers who failed math and are the reason we’re losing ground economically to Asia, here is a Venn diagram:

Venn Diagram

There are a lot of folks who want to write humor, and you’re in the game because you’re doing it. But the trick to get better is to really immerse yourself in it and be brutally, brutally honest when you write and ask yourself, “Is this funny?” and “Would anyone give a shit?” If you’re right more than you’re wrong when you answer those questions, you’ll improve and there will be sweet writer boats and huge writer mansions waiting for you in the future. Good luck.



The Freelance Game

Writer Joe Donatelli drops knowledge on how to succeed at the Freelance Game.


A lot of people want to know how I did it. How did I rise to the middle of the freelance writing game? They come up to me on the street and they’re like, “I want what you got. I want an eight-year-old compact car, an old PlayStation and a streaming-only Netflix account—I want to live the life.” And I’m always like, “Slow your roll, young buck. There’s a lot about this game you don’t know.” It’s not all bylines and Facebook Likes. This is work, and it’s not easy.

For example, when you’re employed full-time by a company, you never have to ask it to pay you on payday. You just get your money. But when you work for yourself, you have to remind companies all the time to pay you your money. If it was up to them, they would keep it and spend it on a new office chair or something. So that’s one thing about The Freelance Game many people don’t realize. Everything a human resources department does, that’s on you now. Don’t know Excel? You better learn it, son, or your invoicing system will be a catastrophe.

That’s just one practical aspect. There’s also the mental challenge. You set your own schedule. That means you can wake up at 5 AM and have all your work done by 2 PM if you want to. Or you can 9 to 5 it. Or you can sleep until noon and work into the night. But it takes discipline. You have to sit your butt in that seat and put in the time. The urge to Facebook or do the dishes or drink the finest Trader Joe’s brand rum all day can be overwhelming. It’s the ability to focus on the task at hand that separates the writers like me who can afford to vacation once a year in the state where they grew up from those who can’t. When I’m on that domestic flight in the economy section eating peanuts from a Ziploc bag I brought from home, people know I’m a baller.

Some people say The Freelance Game will spit you out and break you down. Yeah. I’ve seen it happen too many times. People can’t hack just barely making enough money to stay alive. They want the fresh threads, big house, the Escalade with the putting green. That’s the mountaintop, and not everyone will reach it. So they quit The Freelance Game and take jobs as teachers or whatever. Those jobs pay more and can be very rewarding, but when’s the last time a teacher worked all day in his underwear without getting arrested? Money isn’t everything.

So what’s the key then? How do you do it? Like I’ve said, be organized, put in the work and don’t quit. And there’s another thing—the biggest thing. It’s who you know. People like to pretend it’s their writing skills that land them great gigs, but the truth is a mediocre writer who knows an editor will get an assignment over an outstanding writer who doesn’t know an editor almost every time. That’s not fair, you say? Then get the hell out of The Freelance Game! Fair? You care about fair? You chose the wrong, profession. The only fair you should be concerned about is a job fair.

Meet people. Make connections. Good help is hard to find. If you can deliver, you will get hired again and again, and your editors will refer you to other editors, and you will get assignments out of the blue. That’s when the real money starts rolling in—the we-can-afford-an-apartment-with-two-bathrooms money. Tiny stacks on tiny stacks on tiny stacks. But that’s not going to happen on Day 1, Week 1 or even Year 1. Keep on your grind and maybe someday you can be like me – rolling in so much paper you do not qualify for Affordable Care Act subsidies. The high life.

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Joe Donatelli is a freelance writer and editor. You can follow him on Twitter and Facebook