Although I write almost exclusively on the business applications of the Enneagram, I also get many requests for a small piece I wrote about Winnie the Pooh and how the characters fit into the nine Enneagram styles. Here is an updated version.

It started when my son, Tres, was four years old (he is now 18), and he became obsessed with the Pooh characters from the Disney’s Winnie the Pooh video series (Disney-Buena Vista Home Videos). As is common with children of that age, he insisted on watching them over and over, with his mother (me, in this case) held captive as a way to keep him company.

By the twentieth viewing of the many tapes in the series, I realized that most of the Pooh characters clearly fit the nine different Enneagram styles, which is one of the reasons these stories are both charming and memorable. Here is the list of characters and their corresponding Enneagram types:

The Enneagram According to Pooh

Enneagram Style One: Rabbit

Enneagram Style Two: Kanga (mother of Roo)

Enneagram Style Three: Gopher

Enneagram Style Four: Eeyore

Enneagram Style Five: Owl

Enneagram Style Six: Piglet (phobic rather than counter-phobic Six)

Enneagram Style Seven: Tigger

Enneagram Style Eight: Gorilla (although a minor character, he is central to certain stories)

Enneagram Nine: Pooh

I have yet to figure out Christopher Robin, even after going back to the original books to determine if there were more insights to be gained. Unfortunately, I could not find any more information that was helpful to me. I sometimes think it may be that his character is either not sufficiently developed by author or he might be a hybrid of two or more styles – that is, the author mixed a few types in this case such as Styles Two and Three or Styles Nine and Three.

After my son became very familiar with the many characters, I would ask him “Which one is most like mommy? Which character is most like daddy? Which one is most like Uncle Martin? Which one is most like you?” By the time he was five, he had his immediate family accurately typed. At six years old, he knew who he was (a Three).

As he became older and my list of questions became longer, he was able to identify the Enneagram types of others who were central in his life. When he was eight years old, he was able to substitute the Enneagram numbering system (One through Nine) for the Pooh characters. He learned how to type his friends, teachers, dogs, cats, and even the newscasters and politicians on television. At this point in his life, my son can teach adults and peers the Enneagram system in 15 minutes, and he is quite adept at helping people type themselves.

Those of you interested in the Enneagram and fictional characters might enjoy one or more of the following books: The Literary Enneagram: Characters from the Inside Out by Judith Searle and The Enneagram Movie and Video Guide by Tom Condon.