7 Inspiring Things I Learned During My Weekend With the Oatmeal

A year ago, I spent a weekend with one of the Internet’s most popular — and notorious — creative people: Matthew Inman, the artist behind the viral comic sensation I was writing a story for Wired, following Inman around New York as he explored the late scientist Nikola Tesla’s laboratory.

Having followed Inman’s work for several years, I had a certain picture in my head of who he was and what he was like: clever, quick on the uptake, crass. But after spending time with the guy, I realized that, like most people, there’s more to him than meets the eye. My story focused on online vigilantism, and Inman’s reckoning with the power his massive fanbase gives him (and how he’s used it for good). But the man himself is much more soft-spoken and thoughtful than his drawings of foul-mouthed dinosaurs might lead you to believe.

Sure, we spent some of the time talking about lasers and grizzly bears. Below, however, are some of the more inspirational things I learned while driving around Long Island with The infamous Oatmeal:

1. The fastest way to grow an audience is to consistently create content that people will talk about.

Inman wasn’t a smash hit on his first try. He spent months writing and drawing comics, honing his skills, and split testing what worked and didn’t. He built up a backlog of material, consistently producing comics on a reliable schedule even when hardly anyone was reading him.

When he found a formula that resonated with audiences, his work spread quickly. The key — and the thread that today ties all of his work together — was in telling stories that people couldn’t help but talk about (usually because they agreed or disagreed so vehemently). When that clicked, his audience grew 10x in a six-week period.

2. Technology makes individuals matter.

Inman’s fanbase is larger than many small media companies, and most corporations. It’s only recently that it’s been possible for individuals like him to build media-scale audiences unto themselves. But just as importantly, it’s his focus on individual readers that won him a lot of his early fans. In the early days, Inman tried to reply to everyone who wrote in or commented on his work. Sometimes those were snarky replies to detractors, but often they were grateful and encouraging. That won him rabid support.

3. Work is 10x easier when it’s 2x as fun.

You’ll ride out the bumps in the road if you’re going somewhere awesome. If you’re not excited about where you’re going, you’re much more likely to bail before things take off. Inman was unhappy, and only moderately successful, in his work as a marketer and programmer before he became a comic artist. Today, he’s a #1 NYT bestselling author and has been able to buy his sister and her kids a house.

It’s easier to stay motivated enough to build that backlog of material while nobody’s paying attention, to spend extra time on the details that make a huge difference, when you’re passionate about your work.

4. Creativity is borne of structure.

If I tell you, “Quick, draw something funny!” chances are you’ll have a hard time coming up with something. But if I tell you, “Quick, draw something funny about your boss!” you’ll be able to invent something much faster. As Jon Stewart once told NPR, “Creativity comes from limits, not freedom. Freedom, I think you don’t know what to do with yourself. But when you have a structure, then you can improvise off it.”

Inman has created a system that works for him, with characters and techniques and a story formula that allows him to be funny without feeling overwhelmed by the blank screen in front of him every morning. (His formula, essentially, is to hyperbolize common frustrations (or celebrations) in everyday living, and to illustrate them in a BuzzFeed-style (or, you might say, BuzzFeed uses his style) list format.) <– (That was some crazy parenthetical nesting!)

Inman carries Moleskine notebooks wherever he goes, and when he notices an interesting fact of life, he scribbles it down. “I type it into a giant file, called like Oatmeal’s Massive Comic File, and kind of type an outline of it,” he told me. And then, like a screenplay, he creates text outlines of the jokes before turning to his graphics program to illustrate.

Of course, this leaves plenty of room for experimentation, which is essential. But it’s the constraints of what he will and won’t do that lead to the creative breakthroughs. This is the case with any kind of innovation, not just comedy.

5. Surprise is the key to memorability.

We laugh at the unexpected. No one understands this better than a comedian. If you want people to remember you, surprise them. Inman does this in his comics and offline as well.

Inman told me that at conventions “people come up to me, and they’re like, can you draw me a kitty, riding a millennium falcon, over the Battle of Helms Deep in Lord of the Rings.” When they ask for those things, he says, “I’ll draw something awful, you know, like a cat vomiting.” Sure, it’s disgusting. But his fans remember it. And it makes them laugh. (It’s a certain kind of humor, for sure.)

Learning to tell good stories is one of the most valuable skills in life and work. And the best stories are full of surprises.

6. Life is the best source material for any story.

Inman’s comics come from the shared frustrations of life, like printers jamming or annoying social media users. But as his work has evolved, he’s drawn a lot of cartoons about pets, family, and things he loves. Life is relatable, its stories inherently shareable. And like #4, it leaves room for more thinking about telling a great story and less clawing your brain for ideas.

7. It’s OK to evolve.

Inman started out drawing comics of dinosaurs eating senior citizens; now he draws heartwarming stories about his trusty dog surviving house fires. As I mention in my Wired piece, his audience has shifted from irreverent teenagers to librarians, cat people, and so on. And that’s ok. He’s still the same guy. His audience is just bigger now.

We, too, shouldn’t be afraid of letting go of some things in order to move up to our next great thing.

contently, creativity, featured, Jon Stewart, Matthew Inman, New York Times, Nikola Tesla, NPR, The Oatmeal, Wired, content marketing

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