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When I first became aware of former New Yorker cartoonist Bob Eckstein, it was because he had been hired to create live drawings for the Erma Bombeck Writers Workshop in Dayton, Ohio, where I presented in April.

I was fascinated by Bob’s drawings, which not only captured every speaker’s and presenter’s likeness, but their essence, something definitive about their personality that made it unmistakably them. It’s easy to capture a person’s appearance, harder to capture their character, and Bob was doing it inside of each 75-minute presentation—not only that, but also accompanying it with some well-chosen quote from them that perfectly encapsulated the subject’s central message.

Even if you don’t know the people in these illustrations, don’t you get an immediate visceral sense of them from the drawings?

I was eager to interview Bob for the blog (and my YouTube channel) because I wanted to know how he observes people so minutely that he seems to see right into the core of who they are, what makes them unique and distinctive, and how he translates that onto the page, thinking that it could offer a useful parallel for authors, who must bring to life fully realized characters on the page with only their words.

It was only in looking him up later to prep for our conversation that I learned of some of his many other impressive credits—Bob doesn’t brag. His work has appeared in MAD, McSweeney’s, National Lampoon, The New York Times, Reader’s Digest, the Wall Street Journal and publications worldwide. It’s been exhibited in the Cartoon Art Museum of San Francisco, the Smithsonian Institute, The Cartoon Museum of London, and many others. He teaches around the world, including the School of Visual Arts, New York University, and Yonsei University in South Korea.

“Do you also write?” I’d asked moronically when we first met in Dayton. Uh, yeah—he’s a New York Times bestselling author (Footnotes from the World’s Greatest Bookstores).

Bob did offer a glimpse into how he translates a brief encounter with someone into such an evocative image on the page…but our wide-ranging conversation about his work as a visual artist was bursting with so many other valuable insights for writers, I decided to broaden my focus and share some of it here. (You can see the full interview here.)

Character development

Bob walked me through his process of capturing a person’s essence using the drawing he made of me, which honestly was not only one of my conference highlights but a personal one as well.

He’s not trying to get the physical likeness perfect right away. Bob says he starts with the feel of the person and the message, the mood, just as he does with all his drawings. Figuring out who they are and portraying that on the page isn’t just getting the lines and colors and planes perfect. It’s conveying the affect of a person, their vibe, just as it is for writers creating characters.

When I show friends and family Bob’s drawings of me they generally exclaim, “Oh my god, that’s you!” Unlike when you hear your own voice recorded and it sounds unfamiliar in your ears, even I viscerally recognize how well he conveyed my essence—the way I stand, the way I hold myself, my gestures, expression, demeanor—just as he did with every drawing of all the other presenters. It’s not so much that the drawing looks just like me, but it feels just like me.

This is the feeling authors should give readers with your stories— it’s not essential that they know exactly what your characters look like, but you want to give them a strong sense of who they are right away.

Asking the core questions

Then we started talking about how Bob approaches each drawing, and I loved the two questions he asks himself out of the gate: “Why should people care?” And “What if?”

The first is his way of determining what might appeal to his audience. He wants to define specifically what about his subject matter will engage, invest, entertain, illuminate, or otherwise make the work matter to them—just the way authors must always be cognizant of their reader and how to make them care about their story and characters.

For me the parallel for authors is what I call your central story question—that essential spine of the story that is the reason readers are reading: what they want to know or find out, the question they want answered. It’s what makes your story matter to them enough to keep turning pages.

Read more: “Do You Know Your Central Story Question?”

And then he sparks and feeds his creativity with the second question, What if? This is such a magical phrase for every creative, luring us to explore the possibilities and stretch our imagination. These two questions go hand in hand because the latter is often the vehicle for accomplishing the former.

“What if” is the core of creating story. It allows authors to create complex and faceted plots, imagine twists readers never see coming, to delight them with the unexpected.

Creation and revision

In a recent post from his Substack newsletter (delightfully called The Bob), Bob talked about how he approaches his work through the lens of his most recent book, Footnotes from the Most Fascinating Museums, beginning with uncertainty and persisting into confidence.

We talked about what that confidence means, and it’s more than simply believing in yourself. It means allowing yourself a free hand in your initial creative efforts, knowing that you have the talent and skill and persistence to be able to continue to hone it in subsequent revisions to make it what you want it to be. That kind of faith is freeing, allowing you to take chances, to loose your wildest imagination, to risk failing because you know it doesn’t make you a failure. It’s simply one step on the road to success.

Read more: “George Michael Had It All Figured Out”

Consider every element

It’s not that his artistic detail is so minute. A lot of these drawings have more of a loose watercolor feel. Instead Bob focuses on what’s most important to convey to the viewer, to draw their attention, and leaves some areas more impressionistic, mere suggestions that let readers use their imaginations to fill in the blanks for themselves, making them an active equal partner in his art.

Similarly, in our writing we don’t need to tediously laundry-list every single detail of a character or setting or world, but we do need to carefully and deliberately select the parts we show and the parts we only sketch in so that we don’t spoon-feed readers, but rather allow them to become an active part of the experience and bring the world fully to life in their head.

The words that accompany Bob’s drawings aren’t a separate element, and they aren’t merely captions. Bob gives as much thought to what quotes to add to his illustrations as he does the drawings themselves, because he uses them to further engage readers, to home in on some aspect of his subject that continues to convey the essence of his subject matter.

With his drawing of the International Tennis Hall of Fame, for instance, Bob features artist Carol Newsom’s statue of Fred Perry, but the quote from curator Nicole Markham is a story about tennis champion Andy Murray that conveys something of the spirit of the museum itself in her humor and Murray’s irreverence.

“The point is the North Star of the mood and the objective of where you’re getting with the story,” Bob says, “or what I’m trying to capture with the picture.”

Originality

Bob says he works to surprise and delight his readers, looking for fresh ways to approach each project. For his bestselling Footnotes from the World’s Greatest Bookstores, he wanted the book’s cover to open forward, like a garage door, instead of the traditional sideways, but once inside the pages turn like a regular book. It’s just one of many things that sets his work apart—like the fact that all the quotes that accompany his drawings are handwritten as part of the art itself, rather than typeface superimposed over it.

There are no new stories under the sun—but it’s every author’s job to make each story uniquely their own. It’s what will win readers and create lifelong fans.

Persistence

When I read some of Bob’s impressive credits in our recorded interview, he said, “You didn’t bring up all the rejections and all the projects that kind of fell through, and I think it’s really important for people to realize [that]. There’s nothing more annoying than hearing someone was an overnight success, because it’s not true.”

I don’t have to tell any author that it’s not true in our field either.

Support

Our conversation led us to talk about how important making connections with other creatives is for every artist—not because of what they can do for you, but for what you can learn from them and how they will become part of your support system that every creative needs.

That doesn’t mean “networking” and its usual icky connotation of schmoozing people in a position to further your career in some way. It just means forging genuine connections with people you admire and who interest you.

Read more: “Don’t Build Your Network”

Here’s how Bob and I met: After dinner at the conference one night he and his friend and copresenter, author (and psychology professor) Mark Shatz, approached me because, they said, I was the only other person at the conference they’d heard drop the F-bomb. (In my defense I was reading from a Jenny Lawson excerpt in my workshop, though I make no apologies for my own personal potty mouth.)

I was already enamored of Bob’s conference drawings that I had seen, but when I started fangirling all over him about them, he stopped me to instead tell me in detail what he liked about my presentation and what it taught him and how it inspired him to go home and start working on his own WIP. Bob is more interested in appreciating and learning from others’ work than aggrandizing his own.

“I have this one gift more powerful than any other gift—the ability to surround myself with talented people to learn from,” Bob says. “The important thing is to learn from those people and to create a community, because I’m convinced that you cannot do it on your own.”

It’s that openness and curiosity and willingness to learn from others that feed his own creativity and continually help him grow as an artist, just as it should be for every author. 

Passion

Listening to Bob talk about how he creates his art is exhilarating—not only for the way he describes his creative process, but for his reverence for art in general and how it drives him to try to convey that feeling to his audience. Listen to how he describes his feelings about museums that inspired his latest book:

“I don’t want people to be intimidated by museums. I wanted people to feel that it’s very human. It’s a place that is more organic than you would think—it’s constantly changing.  It’s unexpected. There’s love stories, there’s breakups, there’s everything going on…. The museum is like a giant selfie, because it’s a collection of everything we’ve done on this planet, including our mistakes, and it’s documenting them.”

He calls local independent bookstores “the intellectual hub of our Main Street…it’s such a magical place. Think about how the shelves are filled with people who have all these dreams… You can’t go into a hardware store or a Costco and say that. It’s the one place you have all these people who have poured everything into a book in the hopes that someone’s going to just pick it up.”

Writing is a challenging pursuit and publishing is a tough business. Authors must find ways to keep alive the passion that animates and inspires us even in the face of all this path’s difficulties in order to build and sustain a happier writing career.

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Our full interview ran well over the time I had asked Bob for, because just as I felt when we first met at Erma Bombeck, I could have talked to him for hours about creativity and art. You can see the full interview here.

You can find Bob’s latest book, Footnotes from the Most Fascinating Museums, along with more of his art, books, and other writing, on his website.

And whether you’re a fan of visual art or not, I highly recommend subscribing to The Bob newsletter, which is full of writing tips as well as his wonderful drawings, as well as so much insight and wisdom that’s applicable to our work as writers. (Start with this one, which has such wonderfully applicable insights about revision. And Bob is offering a free lifetime paid subscription right now to anyone who mentions this post or interview, as well as those who purchase his book—it’s the honor system, he says; just mention it in an email.)

If you’d like to receive my blog in your in-box each week, click here.