I first learned about the Enneagram in November 1997 at a workshop put on the Beginning Experience of Winnipeg.
I guess I'd better explain what Beginning Experience is. The Beginning Experience (B.E.) movement began in Texas in 1974, and has since spread to Canada, the U.S., Great Britain, Ireland, Australia, New Zealand and Singapore. The purpose to B.E. is to help separated, divorced, and widowed people to work through their pain and grief, provide a safe space for them to work through their emotional healing and begin a process of self-awareness, and ultimately to free them to live again and love themselves, others and God. It is, at heart, a faith-based peer ministry, organized and led by former B.E. participants (of various Christian denominations) who have undergone some training and have become lay facilitators to help the newer participants through the first steps of the grief and healing process. I went because I had never dealt with my guilt and anger over the failure of my 2-1/2 year marriage in 1991.
B.E. consists of retreat weekends, as well as a weekly "levels" program, levels 1 through 4 of weekly classes. Lower levels focus on the failed/ended relatonship; upper levels tend to focus more on self-awareness and personal growth. After a participant completes level 4, there is a Level 5 available: Enneagram workshops.
I attended two 10-week sessions during 1997-1998 as part of a group of about 20 B.E. facilitators. Our workshop leader was a tiny French-Canadian Roman Catholic nun called Sister Thérèse, a member of the Holy Cross religious community and a co-founder of Contemplative Outreach Canada. I took lots of notes during the sessions, and put them away in a binder, along with my Myers-Briggs personality type stuff, etc. I had to put the Enneagram aside to deal with more pressing matters (i.e. burning out of my job AND coming out the closet to myself). I had other, much more serious, things to worry about than some silly personality system.
Last year, I decided to pull out my 1997/1998 Enneagram workshop notes and read through them again, and I was surprised at how much wisdom there was in what Sister Thérèse had said, and how that fit in with my previous readings on self-awareness (Anthony de Mello, for example). So I made the decision to contact her again. I have since been talking with her regularly as a sort of spiritual counsellor or "guru". I have learned a lot more about the Enneagram along the way, from Sr. Thérèse and from my readings, and what follows is my (admittedly amateur) attempt to explain "what's it all about":