Jason Chatfield’s Infinite Well, A Cartoonist’s Life, A Comedian’s Timing, A 21-Year “Overnight Success"

Jason Chatfield is an award-winning cartoonist, author, and stand-up comedian based in New York City. For 16 years, he wrote and drew the 102-year-old internationally syndicated comic strip Ginger Meggs. His work has appeared in The New Yorker, Esquire, MAD Magazine, Variety, Wired, and more. He’s a former President of both the National Cartoonists Society and the Australian Cartoonists Association, writes the award-winning Substack New York Cartoons with over 19,000 weekly subscribers, and serves as the portrait illustrator for Sam Harris’s meditation app, Waking Up.

But what struck me most in this conversation wasn’t his résumé — which he will massively downplay by the way. It was his discipline and entrepreneurial drive that sets him apart.

Jason talks about treating creativity like a business. About working from a calendar instead of a to-do list. About how jokes evolve from overheard subway moments to stand-up bits to New Yorker cartoons to full book series. And about what it really means to build a creative life over decades, not days.

We talk about failure, imposter syndrome, about backing yourself anyway, and about why chasing algorithms is a losing game compared to serving the people already in the room.

He’s an absolute beast of a creative force.

If you’re interested in the arts not just as expression, but as a way of living, building, and sustaining a career, this episode is for you.