Waking Up

We’re thrilled to share our latest collaboration with you, featuring longtime Waking Up artist and New York-based illustrator Jason Chatfield.

Jason’s work focuses on the joys of process, rather than the completed artwork. Taking pleasure in doing rather than finishing has been a consistent theme in his artistic process for over twenty years.

"These lessons in meditation have become hand in glove with my creative process, opening doors in my mind I didn't know existed."

Jason Chatfield

Waking Up member since 2019

Process Over Perfection

Since 2021, Jason has illustrated more than 100 portraits to support Waking Up Conversations. Each is made by hand using a hybrid process of dip-pen ink line and wash supplemented with digital finishes, specifically Kyle T. Webster's Photoshop brushes, which Jason says “brilliantly mimic real-world tools.”

Jason pulls inspiration from the work of David Levine and fashion illustrators like David Downton, aiming to capture each guest’s personality and spark in their portrait. His biggest challenge, he says, was developing a style of portraiture that could adapt to many digital touchpoints—from dark mode to light mode, and large to small screens.

The real magic in Jason’s portraits, however, comes from vibrant color splatters, which give each portrait a lifeforce.

Playlist

Conscious Classics

As a longtime Waking Up user, Jason shared a small selection of his favorite lessons, meditations, and Moments. If he was in a karaoke bar, he says, these would be his go-tos—the songs he knows by heart. He hopes they stick in your mind in the way they did his.

Listen to Jason’s Introduction:

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Limited Edition T-Shirts

Our collaboration with Jason includes two t-shirts and phone backgrounds, all in his signature style and available now in the Waking Up Shop.
Shop the Collaboration

Or find new art for your phone…

About Jason Chatfield

Jason is an award-winning Australian cartoonist, author & comedian based in New York.

His work has been regularly published in the New Yorker and MAD Magazine, as well as books published by Penguin Random House, Simon & Schuster, and Harper Collins. His art has been exhibited in France, the UK, Australia, and all over the US. He is the portrait illustrator for Waking Up and the Essential Sam Harris series.

His best-selling weekly newsletter, New York Cartoons, has become a Substack Featured Publications for 2023 and 2024. At age 23, he became Australia's most widely syndicated cartoonist and later served as the youngest President of the National Cartoonists Society since 1946.

His latest book is dedicated to his dog and studio assistant, Morris.

Website:
jasonchatfield.com

Substack:
newyorkcartoons.com

Instagram:
@newyorkcartoons