What happens when a nonfiction picture book becomes part literary history, part metafiction, part visual storytelling experiment?
That’s exactly what Annette Bay Pimentel accomplishes in How a Bear Became a Book, her inventive new picture book illustrated by Faith Pray. In our recent conversation on the podcast, we dug into the fascinating collaboration behind the creation of Winnie-the-Pooh, the risks of bending nonfiction “rules,” and how words and pictures can create something neither could accomplish alone.
Watch the full conversation here: YouTube episode
A Story About Collaboration, Not Just Creation
From the opening moments of the interview (0:00), Annette explains that her original idea was far more traditional: a straightforward biography of illustrator E. H. Shepard. But the manuscript wasn’t working.
The tone felt wrong. The emotional truth of reading Winnie-the-Pooh as a child, the way the illustrations and text worked together, was missing.
As Annette shared around 4:00, she realized the book needed to behave like the thing it was describing. Instead of simply telling readers about collaboration, the book itself would become a layered collaboration between words, art, design, and character voice.
That breakthrough eventually led to one of the book’s boldest choices: allowing Winnie-the-Pooh himself to become a narrator.
The Draft That Changed Everything
One of my favorite moments in the conversation comes around 6:14, when Annette describes how critique partners helped unlock the structure of the book.
Originally, the manuscript contained parenthetical commentary from a second voice. But watching fellow writer Eija Sumner explore metafictional elements in her own book, The Good Little Mermaid’s Guide to Bedtime, encouraged Annette to lean into that voice more fully. Soon, critique partners began assuming that the parenthetical voice was Pooh himself.
That suggestion startled Annette, who describes herself as a “rule follower” and primarily a nonfiction writer. But once she experimented with Pooh as a narrator, the manuscript suddenly came alive.
The version that introduced Pooh’s voice became Draft 12.
It’s such a powerful reminder that critique groups are often more than editorial spaces. They’re creative playgrounds where possibilities emerge that the writer alone might never see.
Breaking Nonfiction Rules
Around 16:00, we talked about something many nonfiction writers wrestle with: where is the line between fiction and nonfiction?
How a Bear Became a Book absolutely pushes boundaries. Pooh speaks. The book contains metafictional elements. And the art visually evolves as the character becomes more fully realized.
Annette admitted this initially felt risky. But she drew an important distinction between informational fiction this book, where Pooh is obviously a fictional character, and work that pretends to be factual while inventing material without telling the reader.
Her goal was never to obscure history. Instead, she used Pooh’s voice to illuminate the creative process in a way that traditional biography simply couldn’t achieve.
That conversation became one of the episode’s biggest craft takeaways for me: nonfiction creators sometimes need to ask not “What are the rules?” but “What best serves this story while remaining fair to the reader?”
Discovering That Winnie-the-Pooh Was Revolutionary
One of the most fascinating parts of Annette’s research involved studying children’s books from 1926 at the British Library (21:26).
Looking through contemporary books helped her realize just how innovative Winnie-the-Pooh actually was.
Today, we take integrated picture book design for granted. But at the time, text and illustrations were often treated separately. What made Winnie-the-Pooh special was the way the creators designed the entire reading experience together.
Annette also uncovered examples of early promotional illustrations for Pooh drawn by artists other than Shepard. The results were startling: one Pooh wore fancy shoes and carried a cane; another looked almost indistinguishable from Piglet.
Those discoveries helped crystallize the book’s central insight: the Pooh we know and love only emerged because A. A. Milne and Shepard collaborated so closely.
Neither creator alone would have produced the same cultural icon.
Faith Pray Solved an “Unillustratable” Manuscript
The behind-the-scenes publishing stories in this episode are gold for picture book creators.
At 27:26, Annette revealed that the first illustrator approached for the project declined because the manuscript felt “fundamentally un-illustratable.” The challenge? Pooh evolves throughout the book instead of appearing as one stable character design.
Thankfully, illustrator Faith Pray saw the manuscript differently. She described the process as “unpacking a riddle,” finding visual solutions for the book’s multiple narrative layers.
Faith created stamps based on text from the book, developed systems for Pooh’s ghostly emergence from the page, and even embedded details from her own studio process into the illustrations (30:42). Check out her process in this video.
One especially magical l moment comes around 33:00, when Annette explains how Faith incorporated paint smudges from her own palette and handwritten notes from her own character sketches into the art. The result becomes a visual echo of the very collaboration the book celebrates.
Why Back Matter Matters
We also spent time talking about back matter (37:49), and Annette shared something I loved: early in her career, she assumed back matter was primarily for adults.
Then she met kids who read every single word of it.
That realization changed the way she approaches back matter entirely.
In How a Bear Became a Book, the back matter expands the story world while answering questions the main text raises. It also acknowledges the many modern collaborators involved in creating picture books: editors, designers, art directors, and others whose work readers rarely see.
The result is a book that doesn’t just tell the history of Winnie-the-Pooh. It also quietly teaches readers how books themselves are made.
Trusting the Collaboration
Near the end of our conversation (42:36), I asked Annette what she hopes fellow creators take away from this project.
Her answer was simple and insightful:
She hopes writers learn to trust illustrators.
And she hopes illustrators feel empowered to bring their own creative vision to a manuscript rather than feeling constrained by the text.
That spirit of trust runs through the entire book, and through this conversation.
For nonfiction creators especially, How a Bear Became a Book feels like permission to play more boldly with structure, voice, design, and collaboration while still honoring truth.
And that may be the most inspiring takeaway of all.
You can watch the full episode here: Nonfiction Kidlit Craft Conversations episode on YouTube
