#86 The Way of an Author and Illustrator: Finding Inspiration in Art Featuring Bob Eckstein

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Author/cartoonist Bob Eckstein


I met Bob Eckstein for the first time last summer at the Writer’s Digest Conference. I was honored that he drew me, along with many of the speakers at the conference. We connected again when we were both faculty for the Erma Bombeck Writers’ Workshop this year (Bob was the Artist in Residence). Bob was a firefly there, adding his particular talent and sparkle to each event he covered with his fabulous drawings, cartoons and illustrations. But there is so much more to Bob’s story, and I am delighted to share it here.

In This Episode:

  • How Bob started his unlikely career in writing 
  • Advice for writing stories from a different lens
  • Pivoting in your career to discover new forums for your work 
  • Bob’s live drawing process and how to learn, and grow, while remaining authentic
  • Emerging into a state of playfulness with your work
  • Bob and Estelle’s actionable tips for writers 

Watch on YouTube

About Bob

Bob Eckstein (he/him) is an award-winning illustrator, writer, and cartoonist for the New Yorker, New York Times, Reader’s Digest, Smithsonian Magazine, Atlas Obscura, and many others. His Footnotes from the World’s Greatest Bookstores was a New York Times bestseller and made many ‘Best Of’ 2016 lists and continues to be an ‘Amazon Most Wished for Title’ years later. He is also the author of The History of the Snowman, The Illustrated History of the Snowman, and The Complete Book of Cat Names (That Your Cat Won’t Answer to Anyway). 

His work has been exhibited in the Cartoon Art Museum of San Francisco, Smithsonian Institute, The Cartoon Museum of London, and many others. Eckstein has spoke in over a 200 TV and radio shows like Good Morning America and places like NYPL, Miami Book Fair, The Norman Rockwell Museum, and The Grolier Club. He teaches writing and cartooning around the world including School of Visual Arts, New York University, Pratt Institute and Yonsei University in South Korea. His new book is Footnotes from the Most Fascinating Museums: Stories and Memorable Moments from People Who Love Museums

Connect with Bob


Bob’s Latest Book on Estelle’s Bookshop






Podcast: The Cartoon Pad


If you purchase Bob’s new book, Footnotes from the Most Fascinating Museums this month (May 2024), as a thanks, you will receive a free lifetime subscription to his popular Substack humor newsletter The Bob. You need to notify him by email you bought a copy at [email protected]—he is using the honor system.

Connect with Estelle and Learn About Her Courses

Sign up for Estelle’s Micro Memoir Workshop with Writer’s Digest on May 23. Sign up here.

Sign up for Estelle’s online Editor-on-Call Event in Partnership with NYU on June 13 (link below)


Register for “Making the Cut” with editor for The Cut, Jen Ortiz (a free event, with limited tickets).

Update: The event is sold out on Eventbrite, so join the waitlist here. More tickets may be released.

Sign up for Estelle’s Writing Parenthood Class for NYU. Sign up here

Sign up for Estelle’s Personal Essay Class for Writer’s Digest. Sign up here.



Sign up for Estelle’s Substack, Writing That Gets Noticed

Episodes mentioned on the program

Episode #79: Being Vulnerable on the Page and Finding Empathy in Your Heart Featuring Amy Ferris

Episode #77: Writing Personal Stories with HuffPost’s Noah Michelson

Episode #81: The Art of Shaping a Compelling Story Featuring Maggie Smith

Estelle’s Newest Essays/Articles

I’m Learning to Listen in New Ways (Shondaland)

What to Do PreLaunch to Get Your Book Noticed (Writer’s Digest)

How to Resist the Temptation of AI When Writing (Wired)