Terri Libenson Illustration Terri Libenson Illustration
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Update: After 14 years, comic artist Terri Libenson announced on her website Dec. 10 that The Pajama Diaries is coming to an end. The final column ran this week, and comicskingdom.com will host its archives. "After almost fourteen incredible years, it’s with mixed feelings that I’m announcing the retirement of my syndicated comic strip, The Pajama Diaries," she wrote. "This is truly bittersweet. I’ve always loved writing and illustrating the strip. However, I’ve been fortunate to have other exciting and challenging projects thrown my way, and I just can’t do it all — trust me, I’ve tried."

Terri Libenson apologizes for the state of her office. She knows it’s not what you would expect to see in the workroom of a cartoonist. So brace yourself. 

As soon as you enter her home on a quiet residential street in Mayfield Heights, you find yourself in what Libenson promises is her office. That assurance is needed because, for this nationally syndicated creator of The Pajama Diaries, there is a distinct lack of paper anywhere to be found. No blank pages on the desk waiting to be filled. No storyboarding on the walls or floor. No discarded ideas crumpled up in the trash. The only paper in sight is a small sketch taped to the top of a 16-inch interactive tablet. 

“I know. It’s really neat in here,” she sighs. “My family makes fun of me for it.”

She sits at her desk in front of the tablet, picks up her stylus and begins to fill in the panels of a comic strip that will be printed six months from now. In this particular story, three women are discussing menopause over a bottle of wine. 

Terri Libenson

Her stylus flows effortlessly across the screen, brush strokes creating one character’s hair in long swooping strokes. One woman’s frown is quickly erased and replaced with an upbeat turn of the mouth. Dialogue boxes are drawn, erased and redrawn in rapid succession. 

“I always struggle to make wine glasses symmetrical,” Libenson admits.

With every tiny addition to the panel, she clicks the save button so that none of her work is ever lost. It is a painstaking, incremental process, not at all how you would expect the strip’s Jill Kaplan, Libenson’s alter ego and working mother of two, to come to life. 

But then again, there really is nothing expected about Libenson’s place in the funnies. She is a female cartoonist in a male-dominated field. She draws characters who age in real time when most other comics are frozen in place. She doesn’t hesitate to depict issues of feminism, equality and intimacy in her pages. She has even launched a series of graphic novels, including her latest Positively Izzy, which debuted in May, targeted at preteen girls.

As she tinkers with those wine glasses, Libenson can’t help but smile. She is exactly where she wants to be: in her home, surrounded by her family, creating her art.

The Origin Story

Scene: Jill’s daughter Amy tries on her high school cap and gown and asks her mom, “Well?” Three panels show Amy rapidly growing younger through Jill’s eyes, from teenager to tween to toddler. The last panel shows Amy as a newborn, completely engulfed by cap and gown. “Looks great,” Jill concludes poignantly. Baby Amy replies, “Fits perfectly, don’t you think?”


As with so many cartoonists, it all started with Snoopy. 

A quiet child and the youngest of three in Kingston, Pennsylvania, Libenson began to express herself through doodling on the reams of paper her father would bring home from his paper supply company.

“There was so much depth to Snoopy, Woodstock and all the rest,” she recalls. “Those characters had a huge inner world of complex thoughts, and there was an underlying sadness to it all, even if I didn’t really understand all the layers as a child.”

At 10, she moved from Peanuts to Archie Comics, stealing issues from her brother’s stacks, drawing over them with white-out and colored pencils and redoing the dialogue with conversations she heard in school and on television. 

Comics allowed Libenson to create whole worlds populated with gregarious teenagers living exciting lives in stark contrast to her own quiet existence in the small bedroom community. She collaborated with a neighborhood friend to create original comics depicting the teenagers who led the most dramatic lives possible.  

“We were pretty girly 12-year-olds, and that energy could be felt everywhere in that comic,” laughs Libenson. “Those characters had so much drama that we even had them go on The Love Boat! On those pages, we could create sensational lives we dreamed about but didn’t have.” 

When it came time for college, Libenson wanted to be in an art-related field, but that’s as much as she was able to narrow down her future. She ultimately chose Washington University in St. Louis and majored in illustration. But she had no idea how it would turn into an actual career. 

Then recruiters from American Greetings visited her campus. But there was a problem. 

“They wanted humor writers,” says Libenson. “I hadn’t considered that path before, but I figured, Hey, I could be funny. So I completed the assignment they gave me, was offered a job and off I moved to Cleveland.”

Work Meets Working Mother 

Scene: Jill’s minivan goes from printer to doctor to client to PTA to dry cleaner to pharmacy. Her husband Rob notices a thousand new miles on the van’s odometer and asks her when she left town. Jill puts her hand on his shoulder and says, “I really need to sit down with you and explain my life.”


Libenson spent seven years working full time at American Greetings writing humorous lines for cards, but the desire to create her own comic strip was never far from her mind. 

In 2000, she created Got a Life, a weekly offering based on her newlywed life with her husband, Michael, that navigated finances, setting up a house and deciding on dinner. 

“My drawing skills were really rusty,” recalls Libenson. “I cringe looking back at it!” 

But Jay Kennedy, a longtime editor at King Features Syndicate, liked what he saw and secured Libenson a weekly syndication deal. She went part time at American Greetings so she could manage the job and the new weekly strip. 

Within a few months, she added another huge role: mother. Libenson and Michael welcomed their first child, Mollie, in 2000, followed 2 1/2 years later by their second daughter, Nikki. 

“Those first few years of working, drawing and mothering were like boot camp,” says Libenson. “We got by with a lot of day care and a lot of crying. Someone was always crying when my husband got home. Either my toddlers or me.”

The Pajama Diaries Come to Life

Scene: Jill in the kitchen. Noise, cursing and commotion emanate from an adjacent room. Jill, with eyes tightly screwed shut, holds a glass to the dispenser of the refrigerator, filling it up not with water or ice, but with a third option: vodka.


To cope with the stress of her busy work life plus two toddlers, Libenson turned to other working moms. 

Somewhere between reading the humor of I Don’t Know How She Does It, Allison Pearson’s comic novel about a working mother, and the pathos of Perfect Madness: Motherhood in the Age of Anxiety, Judith Warner’s sobering reflections on motherhood, the thought suddenly hit Libenson that a blend of humor, stress, feminism and motherhood would make for a great cartoon character. 

“I wanted to explore motherhood from a feminist standpoint,” she says. “I thought people would relate to the humor and pathos of a mom who juggles the whole world in her hands every single day.”

For nine months in 2005, Libenson seized rare moments of quiet to develop a strip that mirrored her own life, an autobiographical take on an over-stressed, overwhelmed matriarch named Jill Kaplan. 

Kennedy, her editor, loved the idea and thought it would make for a great daily strip. Libenson originally called her work The Mommy Diaries but settled on The Pajama Diaries for a broader appeal. Through Jill, a mom who works from home and can spend all day in her pajamas, Libenson gave the strip an intimate, voyeuristic quality.

The result is different than the other panels in the funny pages. Here was a female cartoonist drawing a female protagonist who’s the mother of a Jewish family. In addition, Libenson decided to draw the strip in real time so the characters aged along with the audience. 

The unique mix of female cartoonist, self-inspired content and real-time approach had never been seen before. Newspaper editors began to take notice. The Pajama Diaries started in 20 papers and now runs in more than 200 outlets worldwide. 

“Cartooning is still very much an old-boys club,” notes Jenny Campbell, author of the nationally syndicated strip Flo & Friends. “There are only a handful of women who have broken through, and Terri is a shining example. She is consistently funny and unafraid to tackle topics that really happen in women’s lives.”

Embracing Tough Issues

Scene: Jill is in bed with a copy of Modern Moms. She reads, “The problem with ‘Leaning In’? It puts all the burden on women. Meanwhile it does nothing to correct the system. Instead of leaning in, isn’t it time we lean on each other?” Jill pumps her hand in the air and exclaims, “We must band together!” Her husband, with back turned, replies, “Is this a feminism thing or your way of asking me to spoon?”


Libenson turns to her own family for inspiration. As her daughters were prepping for their bat mitzvahs, so too were her characters. Driver’s licenses, college searches and bedroom conversations with her husband all made it into the strip. 

While other illustrators may stay away from covering topics of intimacy, she intentionally pushes to reflect the real, humorous conversations couples are having about their sex lives. 

In a strip earlier this year, Jill discovers that her husband’s desire to have sex is based on him falling short of his daily Fitbit goals. Based on a real-life conversation with Michael, it elicited a ton of reader reaction online. Even strips where she pushes the limits too far — resulting in an editor’s rejection — often end up on her blog for a worldwide audience to enjoy. 

“Terri is extremely kind in not throwing me, aka Rob, under the bus,” says Michael. “Her writing usually positions Jill as the focal point of the joke.”

Libenson has been integrating serious issues that affected women into The Pajama Diaries since the beginning. A 2015 strip saw web designer Jill in bed with her easygoing, IT-working husband, discussing the wage gap between non-moms who make 7 to 14 percent more than equally qualified mothers. Rob exults that “for once he won’t be blamed for something.” Jill quickly reminds him that he too is a non-mom. 

“I’m always looking to highlight bigger issues that are feminist related,” she says. “Working moms especially have been viewed for so long in a negative way, seen as less capable and committed than those who have children. It’s so unfair and completely untrue.”

Death has even made an appearance in her comics. Earlier this year, fans opened their papers to find an obituary posted for Grandma Sophie “Kvetchy” Tetelbaum, complete with a recommendation that readers “make a charitable contribution to the Dead Cartoon Characters Fund (kidding) or to Cure Alzheimer’s at www.curealz.org (real).” 

“I want my comic to reflect real life aging,” says Libenson. “My characters get older so I decided Grandma Sophie dying was a natural progression. It might just be the first obituary in the funnies.”

It’s just one of the reasons the strip has been nominated four times for the prestigious Reuben Award for Best Newspaper Comic Strip by the National Cartoonists Society. Libenson took home the prize in 2016 — and is just one of three women to win the award. 

“Terri is one of the artists I admire and who I look for her on the comics page,” says Tom Batiuk, legendary cartoonist and creator of Funky Winkerbean. “She eschews the obvious idea and is willing to dig below the surface to get into the internal lives of the characters through sharp, smart dialogue.”


From Strips to Books

Scene: Jill pitches a “big idea” to a client. The client throws an arrow into the “big idea” dialogue bubble and it deflates to the ground. A visibly sweating Jill nervously floats a “new idea.” The client takes aim with a whale harpoon. 


With the The Pajama Diaries chugging along for eight years, Libenson noticed other cartoonists starting to produce graphic novels. 

Still, those books were largely written by men. At first, she resisted the idea. She didn’t have the time in her schedule to complete a book project. 

But encouragement came from colleagues who insisted that publishers were looking for female writers who could actually speak to an audience of 8- to 12-year-old girls. In October 2014, she sat down to write Invisible Emmie.

“I had no direction and no outline,” Libenson recalls. “I would just sit in my office and write from my own point of view as a quiet, shy 12-year-old. Suddenly the story started coming to me. I remembered an incident from fifth grade, which became the shocking, I-can’t-tell-you-what-it-is reveal of the book.” 

Mixing pages of text with spot art and full pages of comics, the book offers readers two different styles through which they can view the two narrators: quiet, shy, artistic Emmie and popular, outgoing, athletic Katie as they explore friendships, crushes and developing confidence. 

The resulting book drew a bidding war with nine publishers and a fierce auction to acquire the work. Even more rare in the publishing world, Libenson actually was able to interview editors to make the final selection, ultimately choosing Balzer & Bray, a children’s books imprint of HarperCollins.

Invisible Emmie was an instant hit. Reviewers praised the “spot on middle school humor” and the “heart and wit” throughout the pages. With the success of her first book, Libenson knew she had more stories to tell. In May, she brought forward two characters from Emmie’s world to create Positively Izzy, which explores the theme of labels and characters desperate to break away from them. 

“Writing books is a completely different challenge than The Pajama Diaries,” admits Libenson. “I have learned so much about character development and creating longer emotional storylines.”

Her third graphic novel is due out in the summer of 2019. Although Libenson won’t yet reveal which characters from her previous work are featured in this follow-up, she shares that the theme of the book is exclusion and is based on something that happened to one of her daughters long ago. 

The Juggling Continues

Scene: The bedroom of Jill’s teenage daughter Amy at noon on a Saturday. With Rob at her side, Jill stands over her sleeping daughter with defibrillator paddles and screams, “Clear!”


“Sometimes I’m at the mercy of deadlines,” says Libenson. “Whatever is due next takes priority, whether that is a book deadline, the comics or a parental responsibility.”

She sets a goal to create four strips a day. It is a relentless creative pace, but it’s one that Libenson relishes, even as she sometimes struggles with boundaries. 

Just as her working mom alter ego Jill Kaplan had to put a lock on the door to her home office so that she wouldn’t be tempted to go in during family time, so too has Libenson had to impose limits on entering her tidy office. 

For now, Libenson remains elated to continue to live in that space between what happens in her family and what she draws in the strip. Her oldest daughter Mollie soon heads off to Ohio State University, but Libenson already worked through some of how she’ll feel during this transition by depicting Jill’s eldest daughter’s journey to college, from shopping for dorm supplies to Family Weekend to a house with one less child. Libenson admits that the creative process exists as her own form of therapy, one that takes place on the page six months in advance of the actual events coming to pass. 

When asked for advice for working moms, she puts down her stylus and turns away from the screen. 

“My advice for working moms is to not take any advice,” says Libenson. “Chase what you inherently know works best for you. If that means quitting your job to raise kids, great. If that means working 50 hours a week, wonderful. Just do what you need to do.”

With that, she picks up the stylus and turns back to the screen, determined to fix those wine glasses.

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