Winnie-the-Pooh Celebration Week: Day 2 – How a Bear Became a Book: A Q&A with Annette Bay Pimentel and Faith Pray

You may not have heard it, but this coming Saturday, January 24th is Winnie-the-Pooh Day. And not just any Winnie-the-Pooh Day either! All over the world people are celebrating the silly old bear’s 100th anniversary since the publication of his first books. This week, we celebrate him in different ways.

Truth be told, the idea to do a Winnie-the-Pooh Celebration Week only came to me after Macmillan pitched me the idea for today’s Q&A.

Now it’s not as if we haven’t seen a whole slew of picture book bios of children’s book creators recently. Personally, I like it when they do something a little different. Think, Jim! and its way of presenting James Marshall in the style of his own books. So I will admit freely that when I heard that someone was doing a picture book on the creation of Winnie-the-Pooh I had this knee-jerk reaction to it. Friends, I assumed it would be dull. Friends, I could not have been more wrong. And it’s all because of how author Annette Bay Pimentel and artist Faith Pray decided to get creative with the material. The book in question? How a Bear Became a Book: The Collaboration That Created Winnie-the-Pooh, out March 31st.

Now I could cut and paste the description of the book here from the publisher (as is my usual wont) but I actually really liked how publicist Tatiana Merced-Zarou sold this to me in her pitch. She wrote:

This explores how a writer, illustrator, and editor brought Pooh’s first adventure to life — but deeper than that, it introduces our youngest readers to how stories begin and where they can go. In a starred review, Kirkus calls it “a thoughtful, beautifully crafted title that honors a literary classic on the eve of its centennial and introduces ‘The Best Bear in the All the World’ to a new generation.” And in another starred review, School Library Journal, says it’s “a stunning tribute to a classic that also offers insights into the bookmaking process.”

With Faith’s breathtaking and nuanced visual storytelling (as Pooh’s voice enters the text, he slowly comes to life in the art) and Annette’s delightful text, this is a picture book about the making of picture books, but it is also a masterful exploration of ideas, storytelling, collaboration, art, and most importantly, honey.

And after reading the book I realized that what it’s really doing is showing kids that just because someone’s name is on a book, they’re just one of a large group of people, all working in tandem to make it the best possible literary experience. Isn’t that something?

Naturally, questions abound:

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Betsy Bird: Annette! Thank you so much for answering my questions today! First and foremost, let’s get your Winnie-the-Pooh bonafides in place. What’s your own personal connection to Pooh bear? 

Annette Bay Pimentel: I grew up reading Winnie-the-Pooh and The House at Pooh Corner in highly-tattered paperback copies. Years later, I met the earliest incarnations of Pooh in Milne’s poetry books through my father-in-law. When he was 5, in 1925, a family friend in London sent him a copy of the publishing sensation of the year—When We Were Very Young. He loved the book and when he had kids, recited the poems to them. My husband continued the tradition, reciting them to our kids. Grandpa’s book is pretty bedraggled these days and several toddlers have doodled in it, but I love it and keep it next to my desk.

BB: Okay, those bonafides seem fairly rock solid Now Faith! Such a pleasure to talk to you today as well. And what great work you’ve done on this book! Tell us a little bit about how you were approached to work on this manuscript. What was it that appealed to you about this story? 

Faith Pray: Thank you, Betsy. It is an honor to chat with you about our book. 

My favorite books from childhood were the Winnie-the-Pooh stories and poems. I especially loved them because my dad read them to my brothers and me in all the different characters’ voices, stopping at every page turn to let us soak up Ernest Shepard’s magical illustrations. I’ve always been a huge fan of both Milne and Shepard. Also, I had been wanting to push myself as a storyteller and illustrator beyond my known world for awhile, so when Annette’s manuscript showed up, I was captivated. 

BB: Naturally. Myself, I’m endlessly fascinated by how a picture book creator centers the work of another picture book creator/creation. Annette, there are so many different directions you could have gone with this book. You could have done a rote biography of A.A. Milne, after all. Instead, you artfully mimic a kind of discussion aspect of the books themselves. I mean, walk us through your process. Did you have a clear cut understanding of how you wanted to write this book from the beginning or did it become that in the editorial process? 

Annette: At the beginning, I thought I was writing a picture book biography of E. H. Shepard. There are several great A. A. Milne books out there, but I couldn’t figure out why nobody ever talks about what Shepard brought to the books. When I was a kid, I read the books to myself, without a grown-up’s helpful explanations, and a lot of Milne’s humor went over my head. I relied heavily on Shepard’s illustrations to understand what was happening and what was funny.

Writing with a single focus on Shepard, though, turned out to be tough. He was a brilliant illustrator but led a quiet life, especially in comparison to Milne’s flashier existence. My critique group suffered through many bad drafts, but they kept asking me probing questions until I finally realized that what interests me most in the books is the interplay between words and pictures.

At the same time, my friend and neighbor Eija Sumner was finishing her brilliant metafiction picture book The Good Little Mermaid’s Guide to Bedtime. Although my sweet Pooh is nothing like her salty Mermaid, reading her manuscript and discussing it with her is what helped me shape the give-and-take interaction between Pooh and the narrator. And of course I dove back into Milne’s text so I could echo his voice.

BB: Well, and that entirely different take that you did with the text, Annette, had to be matched by art that was original in its own way. To be honest, Faith, I would not have initially believed that a book about the creation of Winnie-the-Pooh could lend an artist to such creative experimentation on the page. Yet what you’ve done with Pooh here is really interesting. You’ve given yourself such a wide and interesting way to play with text, type, color, and words. Was this something you knew you’d want to do with the book from the start or did you slowly come around to it in the process of creating the book? 

Faith: I love mysteries and puzzles, and Annette’s text was the best sort of challenge. 

Annette and our editor Mark Podesta wrote that they wanted our Bear to emerge out of  words, gradually becoming solid until he was recognizable as Winnie-the-Pooh. When I read that, I could instantly picture how I wanted it to look. The hard part would be figuring out how to make that happen. 

One fun thing about working on How a Bear Became a Book is that we were making a book about making a book, but also about the making of a beloved character, and the magic of collaboration, told in multiple voices. My brain hurt in all the best ways trying to puzzle it all out. When I read through the text, I pictured each voice or piece of the story weaving together, layered over each other in different mediums. So yes, I did know ahead of time what I wanted to achieve, but the process of getting there was a lot like the book we were making – it needed lots of trial and error and experimentation until it felt just right.

BB: Oh, let’s lean into that a little. What was your process for this book? How do you create a bear out of words? And was there a lot of trial and error in the process? 

Faith: Oh, so much trial and error! Let’s just say I experimented with a LOT of techniques before solving the puzzle of what belonged where, and I wrecked a lot of paper in the process. 

Since we were deconstructing and reconstructing the idea of story, I wanted the art to feel collaborative, like each thread of story was its own visual voice. I made the artwork in layers with traditional mediums on different art papers.  The spreads that represent E.H. Shepard’s work are made with tools Shepard used, beginning with pencil, then adding ink, then watercolor. 

Every bear in the book also has a doppelgänger made out of words. I loved the idea of a bear made out of words, but I wanted him to have a chaotic dreaminess, using Milne and Shepard’s actual loopy handwriting and notes as well as pages from my own childhood copy of Winnie-the-Pooh for the words. So I bought a reproduction of  Milne’s handwritten Winnie-the-Pooh manuscript, obtained scans of other papers, art, and letters written by Milne and Shepard, then scanned and printed them in reverse onto freezer paper, finally rubbing the inked pages through the screen-print stencils to form bears made out of words.    

Bears made of words alone were a bit hard to see, and I also wanted to bring in an etherealness to represent imagination becoming tangible. So I created stencils from each bear and some of the other elements in the book, then used a brayer to screen-print those elements onto mulberry paper, which created fibrous, speckled shapes that I could layer into each spread and give them a depth with this faint, airy shape behind the words.  

BB: Amazing. And not something one can figure out by reading the art info on the publication page either. Now you mentioned earlier the challenge of all those multiple voices in the text. Annette, one of the most interesting parts of the book for me was how you continued the discussion of all the people involved in a book by doing it with this book itself! In the back you’ve a section where readers meet the author, the illustrator, the editor, the art director, and the rest of the team. Where did that idea come from? Because it’s mighty neat. 

Annette: With all my books, I’ve felt uneasy that only two of us have our names on the cover. So many people have helped shape them! As soon as I realized I was writing about collaboration, I realized I might have a chance to spotlight other collaborators. I included the back matter section you refer to in my original submission (with placeholders for the names, of course), but I was worried it would get cut in the editorial process. Luckily, the whole publication team agreed to keep it in. 

BB: Well, let’s get into what you were just saying about realizing that you were “writing about collaboration”. I mean, your subtitle even name checks “collaboration”. And I love that you show how many people had to be involved to get Pooh to where he needed to be. And you don’t shy away from some spiky moments (which I really appreciated) like Milne poo-pooing (if I may) the art of Shepard. I think that’s a key component to the book, the disagreements. Was it always in the original manuscript? 

Annette: Yes! The fact that the collaboration wasn’t always easy or obvious was important to me. In fact, in my early drafts, Milne came across as just plain nasty. I find it remarkable how the tense relationship between Milne and Shepard mellowed and matured as the two creators worked across their differences to create something delightful and enduring. I am especially moved that Milne ended up going to bat for Shepard to get him a better royalty deal. I think that’s clear evidence that he came to understand the significant role Shepard’s illustrations played in the success of his books. 

BB: Speaking of collaboration, Faith, your art director on this book was Melisa Vuong. Can you tell us something about what it was like working with her and what her process was? 

Faith: Working with Melisa was a dream. In the beginning, we talked about what we envisioned – heft and height, texture and layers, a hand-lettered title – and she was totally up for trying adventurous things with book design. I have a hard time making decisions, so it was a relief to have Melisa’s expert guidance throughout. The pacing was so tricky! When should our Bear of words turn into a finished Bear? About halfway through the process, I sent Melisa and Mark something like three or four versions of illustrations in states of dress so they could help me choose when the Bear should begin to have pencil, ink, and finally, full color. The book is so much better thanks to all the extra design touches Melisa brought in to make it feel so special.     

BB: Let’s also give a little love and attention to your editor, Mark Podesta. Annette, can you talk a little bit about what it was like to work with him on this book? 

Annette: My other books are straight nonfiction, but this manuscript does quirky metafictional things to tell a true story. I am very lucky that it crossed Mark’s desk because he was totally game for engaging with that weirdness. When he first read it, some of the metafictional elements weren’t totally working, and he suggested that we do a revision together before he committed to acquiring the manuscript. That revision ended up being really fun, both because his emails made me laugh and also because he asked such good questions. He pushed me to give Pooh lots more lines. I recently read the book to a class of second-graders and they laughed the hardest at the parts that had Mark’s fingerprints on them. Collaboration, baby!

BB: And speaking of collaborations, how incredible to see you paired alongside Faith Pray! Faith is doing such incredibly interesting things with the art here. She manages to evoke Shepard without imitating him. And, at the same time, as the Pooh in the story of his creation becomes more clear, the Pooh on the page becomes more clear. Were you aware of Faith’s work before this book? How do you feel about the end product? 

Annette: I didn’t know Faith’s work until the publishing team sent me to her portfolio. Her art is absolutely central to how the book works. Before we landed on Faith, another artist considered illustrating it but ended up passing because, she told us, my manuscript was fundamentally un-illustratable. How, she asked, can you design a character who has to change shape across the book? I panicked, thinking she might be right. But then I saw Faith’s sketches. Faith did the impossible in this book: she created a character who remains recognizable and adorable even as he shifts and morphs throughout the book.

BB: I want to get into that a little. Faith, one thing I admired about your style here was that you were capable of evoking Shepard’s classic style without replicating him. Was that a conscious move on your part?

Faith: I deliberately wanted to pay homage to Shepard because I love his work so much, but I didn’t want to exactly copy it. I studied heaps of books about Shepard and his art, and sketched and inked at least a hundred master studies until I felt I had caught onto an essence of his work, while still keeping a little bit of myself in the styling as well. 

BB: And were there any challenges or unexpected problems in the course of making this, or was it all smooth sailing? 

Faith: I think the trickiest part of this project for me was figuring out how to visually map out different layers of the story and find the right look for each of them. Once I settled on the mediums I wanted, I tried to illustrate each spread on one piece of paper, but when I tried screen-printing onto my watercolor paintings, the paper got mangled and torn. I had to give up on my first idea, and separate the process onto different sheets of paper – drawing, inking, and painting on watercolor paper, then transfer-printing words and shapes onto mulberry paper, and layering them together, which made my paper (and me) much happier.

The historical research part of this project was also a challenge. It required deep dives into books, requesting copies of manuscripts, sketches, and letters from archives, digging up old films of Milne and Shepard writing, talking, making art, walking around near the Hundred Acre Woods, and then sketching all of that to get a better idea of my sense of person and place. 

I love learning, so every puzzle, every new piece of history, every art experiment kind of lit me up.     

BB: That’s awesome. Okay, final question for the two of you: What else is on your plate these days? What else are you up to?

Annette: I have a picture book for very young readers about a migrating turtle who ends up in a dangerous place, Turtle on the Tarmac, coming out in 2027 with Abrams; and Numbers Tell Stories Too, a picture book biography about Florence Nightingale’s pioneering statistical work, coming out in 2028 with Beach Lane. 

Faith: In September, we get to meet my next author-illustrated picture book The Woodland Nutcracker, which is a book of cutie pie animals in the Nutcracker ballet. It’s sweet and sparkly, and comes out September 8, 2026 with Abrams. I have another Woodland book coming out in 2027, and a few of the things I’m cooking up haven’t been announced yet. I can tell you I am planning zoo trips and visiting cat cafes, all for research. I also recently stumbled onto mono-printing and am trying to learn all the things there are to learn about that.   

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That’s how it’s done, people!

HUGE thanks to Annette and Faith for taking all this time, love, and attention in answering my questions today. And thank you too Tatiana Merced-Zarou and the team at Macmillan for helping to put all this together. How a Bear Became a Book: The Collaboration That Created Winnie-the-Pooh is out March 31st absolutely everywhere. You’re literally going to love it.

Filed under: Best Books, Best Books of 2026, Interviews