New Yorker Cartoonist Emily Flake Gives You Permission to Write and Draw Jokes at Hillsdale Workshop Experience
The Workshop Experience Weekend in Hillsdale returns for its sixth year with over 26 hands-on classes, and one of the most compelling is a two-hour deep dive into the art of the gag cartoon.
Emily Flake has been drawing cartoons for The New Yorker long enough to know where the labor of her whimsical craft actually lives. It’s not the draftsmanship. It's the joke.
"Ideas are far and away the most important part of the whole process," she says. "The art serves the idea. Either you can draw it yourself, or you can have somebody else draw it. But the paramount thing for me is the jokes."
That conviction is the engine behind "How to Write and Draw Jokes," a two-hour workshop Flake will lead on the morning of May 31 at Taconic Ridge Farm in Hillsdale, as part of the sixth annual Workshop Experience Weekend. The event, organized by the Hillsdale Workshop Alliance, runs May 30 and 31, and spans more than 26 classes, demonstrations, and experiences spread across a constellation of distinctive local venues.
A self portrait by Flake.
Flake runs the workshop primarily as an idea-generation class, using the structure of a single-panel cartoon only as a vehicle for the larger mission: sending people home with tools they can actually use to extract their creative ideas from inside their brains. Timing, composition, what makes a joke land. The craft in service of the concept. And she's candid about what a two-hour session can and cannot do. It isn't, she notes with dry precision, going to get anyone into The New Yorker. The point is something more fundamental, something she says adults rarely give themselves.
Permission to Goof
"Adults really need permission to try," she says. "A two-hour one-off is kind of a perfect cover for that." The class becomes a sanctioned experiment, a low-stakes occasion to poke around and see what's there. And what's often there, Flake suggests, is more than people expect. Everybody, as she sees it, has something quirky and funny rattling around inside them. The workshop is just the occasion to let it out. For those who want to go deeper, she also has an interactive deck of cards on the subject called Joke in a Box.
Flake has been a staff cartoonist at The New Yorker since 2008 and also writes for McSweeney's, the New York Times, and the Wall Street Journal. She has written for television, and teaches a graduate seminar called Drawing for Writers at the New School. In her free time she founded St. Nell's Humor Writing Residency in Williamsport, Pennsylvania, a program she launched during the pandemic after crowdfunding the purchase of a three-story brick house in the birthplace of Little League Baseball. St. Nell's offers free two-week residencies to women, non-binary writers, and people of marginalized genders working in any humor discipline, from stand-up and satire to cartooning and screenwriting.
Jim Carden, a coordinating member of the Workshop Alliance and owner of Taconic Ridge Farm, which hosts many of the weekend's events, has been championing Flake's inclusion since hosting her at one of his Brooklyn performance venues. Carden owns Union Hall and The Bell House, where he met Flake. He thought she’d be a slightly offkilter addition to the always impeccably curated workshop lineup.
"It's amazing, because you don't even have to be a good illustrator for this," he says. "I think a lot of people have great joke-telling skills but don't think of themselves as fantastic illustrators. This class creates an opportunity to explore those skills in an easy way."
What Else to Know About the Weekend
The Flake workshop is just one of the distinctive offerings on the schedule, but the weekend as a whole reflects something Carden has been helping build toward for six years: the idea that this region, sitting two hours from New York City, can offer a kind of hands-on creative learning that's hard to find anywhere. "I've always loved rural living," he said, "but to live in a rural setting where there's so much art and culture close at hand, to me, is just the dream come true."
That mix is on full display across the two-day lineup. Some of it has already sold out. Dan Pelosi's meatball-making class at HGS Home Chef is gone, as is Molly Levine's late spring pasta session and the Saturday knitting class at Nobletown Fiber Works with Lizz Hill Wiker. Margaret Roach's open garden event sold out as well. The appetite, clearly, is there.
But plenty remains. On Saturday morning, Norah Maki leads an introduction to bookbinding at Taconic Ridge, a class the organizers had been trying to land for years. Participants make a hand-stitched, soft-cover journal from scratch. That same morning, also at the Farm, Diana Rupp teaches the art of pressed flowers, and Luke Sarrantonio leads a forest and fungi ecology walk with a mushroom gardening Q&A. Over at Nobletown Fiber Works, Margot Becker takes participants from raw fleece all the way to spun yarn. Saturday afternoon brings Aaron Zimmerman's generative creative writing workshop, designed for writers of any kind who want to get better at starting, and a one-day choir experience led by Kenter Davies.
A one-day choir experience led by Kenter Davies.
Sunday sees Kevin West's cooking class on garden-fresh herbs at HGS Home Chef and Holly MacCammon leads a genealogy session focused on Revolutionary War-era ancestors. The afternoon opens up into nature, with a geological survey of the Hudson Valley with Robert Titus and a bird observation walk with Ben Nickley.
And then there is the weekend's first-ever class for children. Held Saturday morning at Tiny Hearts Flower Shop, it's a flower arranging open house where kids pick their own container and build something with a little guidance.
After a decade of writing for RI (along with many other publications and organizations) Jamie took over as editor in 2025. He has a masters in journalism from NYU, a wonderful wife, two kids and a Carolina dog named Zelda.