comedy writing

Case Study: How To Build A Writing Career

The following is part of my Case Study series of articles in which I offer specific advice to a Connected Comedy VIP member based on their personal goals. If you’re interested in being the subject of a Case Study article, email me.

Connected Comedy VIP member Conn Williams is an Australian who recently moved to Boston, started doing standup about a year ago, and told me he’s ultimately interested in “writing for cinema and TV.” He’s been writing (or as he put it, “trying to”) for nearly 10 years and faces a very common problem.

Here’s how he described it:

“I have started a million projects, but rarely do I get anything finished, certainly never to a marketable point. Project ideas I have vary from novels, movies, sitcoms and documentaries.”

As with most things, there’s no one single way to build a comedy writing career, but I do think there are some mindsets and specific things you can do that will help you get to where you want to go. Following are a few suggestions for how I’d recommend approaching a writing career – and while these are directed toward screenwriting, most of them are just as applicable for your budding standup career as well.

1. It Only Matters If You Finish

In describing your writing background, one sentence stood out to me that rings true to most people who initially pursue a comedy career – “I have started a million projects, but rarely do I get anything finished.”

This is something everybody faces in the beginning, but it’s the most important thing you need to change in order to succeed at whatever you want to do.

What you start is meaningless. The only thing that matters is what you finish.

A finished screenplay that’s terrible is more valuable to you than an unfinished screenplay that’s good. Writing is a tough discipline and no matter how talented you are, the chances are you’re never going to be happy with early drafts of your work.

But you can’t let that prevent you from actually finishing that work.

Abandoning projects creates a cycle that prevents you from making progress – you don’t learn as much as you will learn by finishing things and you wind up jumping from project to project without having anything finished to show for all of your time and efforts.

Don’t worry about perfection, make finishing the project you set out to write your first goal. And take satisfaction from accomplishing that goal – even if your work isn’t great, it’s a huge accomplishment just to complete a screenplay or novel.

Again, most people DON’T finish things. So just by getting to the finish line, you already start to separate yourself from the pack of wannabe writers and are closer to becoming a professional writer.

The other amazing thing that happens when you finish something is that it creates momentum to fuel your next work. As you become a writer who finishes what you start, your skills will improve, you’ll become less critical of yourself, and you’ll learn what it takes to actually write for a living.

You never get paid to start things, you get paid to finish them. So the sooner you learn to finish, the better.

2. Read Scripts. Watch Movies. Repeat.

If you’re serious about a writing career, then you need to read as much as you write. Read the kinds of screenplays that you want to write – it’s not enough to just watch movies.

Screenwriting is its own unique form and you’ll learn a lot by seeing how other writers do it. And analyze what you read – break down the way writers handle scenes, characters, and plot structure. You’ll be amazed how much you can learn when you look deeper than just watching a movie.

Speaking of which, it’s especially helpful to read scripts and watch the movies simultaneously – you’ll get a feel for how the writing translates to the screen and vice versa. If you’re writing a movie (or TV show for that matter), remember that you’re ultimately writing “actions” – even if it’s dialogue heavy.

Studying scripts in concert with the final filmed product will help you learn how to do that.

Also, while the above advice is mainly for film or TV narrative writing, the same applies for novels, sketch, or any other kind of writing you’re interested in. Study how others do it and then put your own spin on it.

3. Tap Into The Online Writing Community

The biggest advantage to trying to build a writing career now compared to a decade ago is the incredible volume of resources available to up and coming writers now online to learn more about the craft.

There’s a HUGE community of professional (and hopeful) writers online and an almost infinite number of blogs, message boards, podcasts and more that feature discussions and advice about how to become a better writer.

This is an invaluable resource (if you access it) and I recommend you deeply immerse yourself in that world. You’ll be able to learn tons of valuable lessons (for free) and you also may find yourself developing relationships with other writers in the community who can help you in a variety of ways down the road.

If you want to be a writer, then one of the first things you should do is become a part of the writing community.

Here’s a few specific recommendations of things you might want to check out, though there’s certainly a lot more out there.

The Scriptnotes Podcast

Reddit’s Writing and Screenwriting subreddits

The Writer’s Bloc Podcast

The Creative Spark video series

10 Influential Screenwriting Blogs

4. Produce Something

While it ultimately may take a lot of money and somebody else to fund your movie or TV screenplay, write something small and figure out a way to actually get it made.

Whether it’s a short film, a web series, play, or even a scripted podcast, figure out a way to write something you can turn into a finished, created, “real” product that exists in the world.

You can team up with other producers, filmmakers, and actors – you don’t have to do it all yourself, but it’s important to go through the process of seeing your words come off the page and be brought to life.

Doing this will provide multiple benefits for you. You’ll learn a ton from seeing the difference between writing words on a page and how they’re actually performed and shot – that will ultimately help the quality of your writing in the future.

You’ll also benefit from having the opportunity to see how an audience (even a small one) reacts to one of your creations – that too will help your writing.

Maybe most importantly, you’ll get to have some fun seeing the things that came from your head become real and that will give you some much-needed momentum boost to encourage you to keep writing. There’s something about seeing creations become real that motivates writers to create more.

And finally, if you actually put something out into the world, you never know what new opportunities it may create. Maybe your video will go viral, maybe your web series will develop a following, maybe somebody influential will see it and want to work with you on something else.

5. Take Whatever Work You Can Get In The Industry

In addition to spending a lot of time writing, you’re going to want to find ways to make connections with other people working in the industry because ultimately you’re going to need to get to those people in order to sell your script or get yourself hired to work as a writer.

One of the best ways to do that is to take any jobs you can find that are remotely related to the industry you want to work in. Don’t worry if it’s not necessarily a writing job, if it puts you anywhere near anything that you’d want to be involved in, then go for it.

Working on the crew of a production or getting coffee as an assistant for somebody may seem like a waste of your time, but it’s not. It’s an opportunity to get to know people who are in positions that can ultimately help you and you’ll find yourself surrounded by other people who have similar goals and connections. Do whatever you can to just get in the door at an entertainment company and then figure out the rest from there.

For an industry that’s so huge, the entertainment business is a surprisingly small world – everybody kind of knows everybody – and today’s assistant is tomorrow’s studio head. Take whatever job you can find – even a part time gig where you work for free if you have to – to put yourself into that universe. It will ultimately pay off in a big way down the road.

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5 Things You Can Learn From Saturday Night Live’s Youngest Writer

Author and comedy writer Simon Rich, the youngest writer ever hired on Saturday Night Live, recently appeared on the James Altucher podcast for an interesting look at his approach to writing comedy.

In the conversation he shares his thoughts on writing vs. standup comedy, how he comes up with stories, and why he believes emotion is everything.

You can listen to the full episode here, or read up on some of the highlights below.

1. You Have To Be A Superfan First

At around the 9-minute mark, Rich discusses how he got his start in comedy writing and how he believes most people do – by being a superfan first. He points out that for most people who “make things” for a living, it starts with them being obsessive fans.

Rich grew up watching tons of comedy on TV, particularly noting how he would obsessively watch sketch shows like Mr. Show and the Upright Citizens Brigade TV series.

“I was always trying to copy my heroes,” he says.

But his biggest influence was The Simpsons, noting at the 46-minute mark of the podcast that, “Everything I believe about comedy I learned from The Simpsons. In my mind, it’s the most perfect work of art.”

2. You’re Probably Either A Standup Or A Writer – Very Few People Are Both

At around the 17-minute mark, Rich weighs in on the differences between performing standup and writing comedy, and explains why he believes people are rarely good at both.

Calling standup an “extremely hard skill,” he points out that you can be a good standup and not a good writer and vice versa – there isn’t necessarily any overlap in the two comedy art forms.

For himself, he realized early on that he was drawn more to writing than performing so he chose to focus on writing.

“Usually, standups love performing – they can’t wait to get on stage,” he says. “It’s a very different thing than what I do.”

3. Everybody Tells The Same Stories

At around the 23-minute mark, Rich goes into a very interesting explanation of how he actually approaches writing.

“A lot of what I do is taking an old story I love and making it my own with a twist,” he says.

He goes on to explain that some people believe there are really only a couple plots that exist in the world and that every story is a variation on them. He believes there’s more like a dozen plots out there for people to reinvent, but agrees that everybody is pretty much telling the same stories in different ways.

Rich approaches his writing by looking for the emotional core of a story and finding ways to amplify that emotion, which is where the comedy is found.

“I start with a visceral emotion I have felt [in real life],” he says. “If it feels universal, I’ll write about it. I try to write about emotions not in the way they actually occurred, but in the way they felt. It feels much more high stakes than it is.”

For example, a broken heart in a relationship might not actually be the end of the world, but it feels like the end of the world. So he writes about it being the end of the world.

Later in the podcast, Rich adds that once you hone in on the stories you want to tell you can continue to tell them in different ways forever. “Some people write the same story for their whole lives,” he says.

4. Comedy Is Vulnerability

At about the 30-minute mark, Rich talks about how important he believes emotion is to comedy writing – and especially vulnerability.

“At the core of every comedy premise there needs to be some vulnerability, somebody has to be weak,” he says.

He goes on to talk about how challenging it is to incorporate an emotional connection into sketch comedy writing, which is one of the reasons he’s currently adapting one of his books into a sitcom instead of a sketch show.

He points out that audiences have a tendency to write off sketch shows and not allow themselves to become emotionally invested in them because you’re constantly reminded that what you’re watching is fake as a result of the characters constantly changing.

He contrasted that with a sitcom, where viewers get to know the same characters and develop an emotional connection to them relatively easily.

“Every new SNL cast member is hated at first because the audience doesn’t recognize them,” he says. “With a sitcom, by episode two or three you know the character. They always look the same.”

5. It’s Never Too Late

At about the 54-minute mark, Rich offers some words of encouragement to other would-be comedy writers who may be unsure of whether they’re making any progress or if they’ve waited too long to chase their dream.

“It’s never too late,” he says. “But if you don’t love sitting down and writing then you definitely shouldn’t do this because that’s what it is. But if you think you might like it, then you should sit down, write, and find out.”

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