This hilarious New Yorker cartoonist has the best advice for how to use self-doubt to your advantage

About a week ago, after having the violent realization that I’ve been doing everything wrong, I came across a blog written by a guy named Jason Chatfield. As it turns out, Chatfield, comedian/vice president of The National Cartoonists Society/cartoonist for The New Yorker and Mad Magazine, is a productivity machine that knows the failure epiphany I was currently experiencing, in the biblical sense.

Raised by a single mom, in a small duplex in the suburbs of Perth, in Western Australia, he learned very early that the only effective tactic against self-loathing is consistent output. “There is any number of books you could read to try and convince yourself that ‘you’re worth it’ and ‘worthy of your success’ etc. but ultimately it’s you that has to attach your name and worth to your work –and find a way to get comfortable with it,” Chatfield told Ladders.

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The blog that inspired our interview revolved around the importance of assigning deadlines. When you leave tasks in the care of a to-do list, you tell yourself that these tasks should get done but not that they need to.

To encourage accountability, Chatfield works from a calendar. Every assignment receives a target date, once it gets completed, he notes the amount of time it took him to do so, so he can better estimate windows of completion for similar errands in the future.

Sage advice, though, in truth, the medium post that animated our chat ended up being the jumping-off-point for an honest discussion about working through unrelenting self-hatred. We eventually returned to the importance of deadlines, but the scenic route yielded a lot of valuable (and relevant) insights.

Phantoms of expectation

Growing up, Chatfield’s free time was divided evenly between making people laugh and sketching cartoons in his room. I wondered if the luck of landing a job that pays him to do both came with any sort of comparable pressures.

“I think a lot of creative people who earn their living doing what they love have to deal with a combination of impostor syndrome, fear of where their next paycheck is coming from and fear that they will wake up tomorrow and their ideas will have all dried up,” Chatfield told Ladders.

The fear of being found out exists across all industries, though the conventional tricks never seem all that considered; the bulk of them are just dense-wordy riffs on the little engine that could.”Believe in yourself,” is a vague piece of advice that only really applies to a small minority. I think it’s more comforting to know that most of us are right about our incompetence. Ultimately, anxieties will always stand between us and a finished project. It doesn’t really matter if they’re based in truth or come from within, we have to learn to work in spite of them. Chatfield believes his ability to silence the beckon of self-sabotage, was authored by his mother, as he watched her navigate self-employment against the odds in order to provide for him and his sister in their tiny duplex.

“I witnessed some first-grade freelance hustle. My mom now has a successful, thriving business 25 years later and remains my model for work ethic. I started my freelance business at a drawing board in my tiny bedroom of that same duplex 15 years ago,” Chatfield recalled.

“You can make good work if you hate yourself very much”

But managing to live a  productive life with full-blown masochism isn’t just about suppressing it; you also have to learn how to weaponize it. The self-prodding that keeps many professionals from getting a good night’s sleep energizes Chatfield to prioritize daily tasks. When looking at a list of things that need to get done, he asks himself: “What’s the one thing you need to do today that will let you go to bed tonight without staring at the ceiling, stressing that you need to do it?” Those things get done first. Chatfield then applies, the measured strategies featured in his monthly blog, “it’s never answering every email in your inbox before getting started. Working from a calendar also kills procrastination because it not only tells you what you have to be doing now but tells you exactly what you’re going to be doing next.”

Jason Chatfield
Jason Chatfield

Pitching is a consistent feature of Chatfield’s day. Without knowing it, he echoed one of the things I’ve always found the most difficult about it: “How do I get this idea across without my colleagues finding out that I’m a loser-idiot?” Chatfield expounds,

“Pitching should be a death-row alternative for murderers. Every Tuesday at 11 AM, I go in person to the World Trade Center and pitch 10 drawn-up ideas to the Cartoon Editor of the New Yorker and inevitably get maybe one in ten put through to the Editor in chief. The odds of getting a cartoon in the New Yorker are crazy. Last year I pitched 387 ideas and they bought 12 (that’s pretty good for the New Yorker.)”

Warding off phantoms of expectation requires an appetite for honest and sometimes dispiriting feedback. Chatfield takes the commentary of his colleagues in stride, irrespective of its nature. The desire to make good work, has to be greater than the fear of disapproval.

“I have a daily comic strip that goes out 7 days a week to 34 countries, translated into different languages. Over 12 years I’ve figured out what the editors and readers do and don’t like, through the slow process of feedback and development. So I have a ‘comic strip’ editor in my head,” said Chatfield.

Playing to your audience

This similarly applies to his process as a stand-up comedian, where his editors are his audiences. “As a comic, you know something isn’t working if people aren’t laughing; it’s a fairly basic feedback process.” This was particularly relevant to me because of how often I assign undeserved credence to the tiny defeats that are necessary to actualizing lofty ambitions.  Chatfield believes many of us confuse, self-hatred and arrogance. When I relayed to him, my awful method of pitching ideas, the majority of which leave my mouth as rambly-incoherent-nonsense infected-jargon-from-an-Asylum-escapee, he suggested I try pitching ideas, under the assumption, there was no way anything I said had the ability to convince anyone of anything they didn’t already know or think. This way, our ideas come out more honest, and with less wordy baggage.

Chatfield was introduced to this ideology, via an accomplished writer, Elizabeth Gilbert and her book  Big Magic: Creative Living Beyond Fear. “The best advice I could give as a ‘key’ to anything, is to approach it knowing that nobody owes you anything. You may well have worked hard at something, but the world really owes you nothing in return. Doors won’t magically open for you and work won’t miraculously get done for you. You have to be ready to make the most of every opportunity as if it’ll be your last,” Chatfield summed up at the end of the conversation.

Be sure to check out Chatfield’s meditations, in all of their incarnations. And if you get a chance to see him live at a comedy club in New York City I highly recommend you do. He knows how to work the audience.

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