Enneatype 9 is often described as "going with the flow", "not rocking the boat", "going along to get along." It's said that when pushed too far they can become stubborn and "dig their heels in." What could possibly underlie this sort of behavior?

It may be true that most, if not all, type 4's have been depressed at sometime in their life. That may also be true of many Enneagram types. With type 4, depression, sadness or melancholy can arise as a byproduct of other processes or triggers.

The Epicure, The Enthusiast, The Adventurer, The Visionary, The Dreamer, The Joyful Person and The Futurist are all labels used by authors to describe Enneatype 7. The common thread seems to point to someone with a positive anticipation of the future that seeks out new and exciting possibilities. Does this approach to life lead to happiness or an endless pursuit of happiness?

Stereotyping the Enneagram types can be understood in terms of inductive and deductive reasoning. The inductive approach goes from details to generalizations while the deductive approach starts with generalizations and moves to details. Although using one or the other approach exclusively can easily lead to stereotyping, it seems to me that the deductive approach to typing leads to stereotyping more often (especially with people just learning the Enneatypes).

"The Helper" is by far the most popular label given to Enneagram type 2 by the Enneagram authors, yet all nine types are helpful in their own way. In his book Ennea-Type Structures, Claudio Naranjo gets closer to the reality when he labels Ennea-type II as Egocentric Generosity. He goes on to describe the seductiveness of type 2 in this way.

For those who haven’t followed Eliot Spitzer in the news, in 2002 Time Magazine named him “crusader of the year” for the way he took on greed and wrongdoing when he was the New York State attorney general. In 2006 he was elected New York’s governor by a historic winning margin. In March 2008 however, the trapdoor to his personality was revealed when the story broke about how he was a repeat prostitution customer.

Type 3 seems to get a bad rap because of their chameleon-like ability to take on the identity valued by whatever group they're trying to become a part of. Three points I'd like to make about this:

Don't confuse emotional expression and feelings. Lack of emotional expression on the surface can belie a richness of feelings within. Just because someone doesn't want you to see their feelings, don't assume they have none or that they're not very aware of them. Sometimes the most emotionally expressive people are those least in touch with their feelings.

Stereotypes about the Enneagram types come about when only a narrow set of characteristics are taken as a representative generalization. This can easily happen to someone new to the system.  Here are some example type stereotypes:

Without justice there can be no peace...
- Martin Luther King Jr.

I can think of no more succinct way to describe the Enneagram 8 with a 9 wing style than the above quote by Martin Luther King, Jr. - type 9's desire for peace and type 8's desire for justice.