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.

Join Tad Crawford—author, publisher, and attorney—as he explores the emotional core of his latest novel, A Woman in the Wild. Through the journey of its protagonist, Thea, Tad reflects on family estrangement, the healing power of nature, and the tension between creative instinct and practical reality.
Tad’s multifaceted career includes decades of work supporting writers and artists, notably as co-author of The Writer’s Legal Guide: An Authors Guild Desk Reference, a foundational resource on copyright, contracts, and publishing law. His background as an advocate for creators informs this deeply personal and literary conversation.
The episode also touches on the ethics of AI, the philosophy of money, and the role of storytelling as a means of understanding and healing. A thoughtful exploration of creativity, independence, and what it means to build a life on one’s own terms.

Join us in this captivating episode as we sit down with Paulette Perhach – an acclaimed author, essayist, and writing coach. Paulette shares her journey of helping writers through her innovative tools and community initiatives, such as the Writer's Mission Control Center and The Finishing School for Writers. Dive into the emotional aspects of the writing process, the struggles with ADHD, and the importance of community in overcoming writer's block. Paulette also discusses her viral essays, the evolution of her writing career, and her unique perspective on balancing creativity with the business side of writing. Whether you're a budding writer or a seasoned author, this episode is packed with insightful advice and inspiration.