Note: This piece reflects a personal journey with the Enneagram between 2013 and 2018, including conferences, workshops, and informal conversations. The impressions here are subjective and based on lived experience rather than formal study. I remain intrigued by the Enneagram as a reflective tool, even as I view aspects of the professional community with some skepticism. As always, this is written in a spirit of curiosity, appreciation, and lightness rather than critique for its own sake.

Epigraph
“We’ll take the Skyway / high above that busy little one way”
— Skyway, The Replacements

I first heard of the Enneagram in 2013 at a six-day beginner NLP training in Singapore run by a company called Mind Transformations. The training was led by Barney Wee, a tightly wound but candid guy who shared a lot about his life — past struggles with party drugs, his mentally challenged son, his strict vegetarianism — all delivered with a kind of intense openness that set the tone for the week. His right-hand woman, Angus Lau, was the mother and the emotional center of the operation. Warm, encouraging, and deeply comfortable in what she herself called “woo-woo,” she talked about Sedona hot springs, New Age energies, and personal transformation with complete sincerity. I hit it off with her immediately. She praised my small contributions, which felt good, and we bonded quickly.

There was also Bae, Barney’s younger assistant, mid-twenties, cheerful, cute as a button, and she did props and logistics. The first night in the hotel lobby she broke out a strange psychology-themed board game and we played for a while, and somewhere in the middle of that conversation she mentioned the Enneagram. It was the first time I’d ever heard of it. I was intrigued. On the way back to Japan I stopped for one night in Singapore, wandered into Kinokuniya at Takashimaya on Orchard Road, bought a few introductory books, and started reading them on the plane home. That was the beginning of what I later came to think of as my curious apprenticeship.

For a few years, it was just reading. I typed myself as a 5w4 with a strong 8 lean, which felt roughly right, and I found the system evocative — not scientific exactly, but suggestive, like personality poetry. It seemed to capture tones and tendencies rather than fixed truths, and I liked that. I read more, thought more, and gradually became curious about the actual community.

My first conference came in August 2016 in Minneapolis. I stayed at the hotel hosting the event, down in a quiet basement space, and we were the only people in the area. It was close to the arena where the Minnesota Timberwolves play, and you could walk there through the Skyway, which made me think of the Replacements song which provides the epigraph, and gave the whole weekend a slightly Midwestern, slightly melancholy frame.

I arrived early the first morning — nervous, excited, and very aware that I had done a fair amount of reading but had almost no real-world experience. I grabbed coffee and sat with a pleasant older couple from the Midwest, and before long I was talking about peak experiences and epiphanies and probably talking too much. I was jittery, caffeinated, and eager. They were kind and listened. Later, when I checked the program, I realized the woman was one of the main presenters and a big deal in the community. Run roh. But it was fine. That, in retrospect, was my first brush with the gentle hierarchy of the field.

I also met Jessica Dibb from her Shift Network podcast, which I had been listening to a fair bit and paying far too much for. She was warm, generous, and exactly as open in person as she sounded online. I liked her immediately, and I still think she was providing a real service to the community. But she also seemed, in a way I would come to recognize more clearly later, very much inside the tent. On the podcast, she rarely pushed back, even when guests — including Russ Hudson — leaned on origin stories involving the so-called Desert Fathers that were total bullshit. I knew they were bullshit, and what was worse, he knew it too. And yet there he was, repeating them ad nauseam. The more I heard those claims, the less convincing they sounded. There’s no clear historical transmission, no diagram, no nine-type personality system — just thematic similarities retroactively elevated into lineage. At a certain point, it stops sounding like history and starts sounding like branding. Sorry, but it’s just a bunch of bull. And yet no one inside the community seemed eager to challenge it. The culture, I began to suspect, rewarded agreement.

The rest of Minneapolis was a mix of seriousness and absurdity. I skipped a packed session by Jean Houston — a decision I later half regretted — and instead attended a tiny aromatherapy session run by two Southern women in matching green shirts who were clearly there to sell oils. They were GENKI as hell and the whole thing was unintentionally hilarious. Each day ended with a drum circle led by a ponytailed New Age facilitator, and I found myself unexpectedly moved, tired and open after long days of conversation.

I met a towering gay guy named Ron selling singing bowl CDs, and eventually I met Jean herself. She was drinking white wine, I was drinking red, and she was as warm as could be. We talked about Japan, about why I’d come, and then we danced together for twenty minutes. She killed it. That moment — generous, playful, human — felt like the community at its best.

Two years later I went to the European conference in Amsterdam. By then I felt like I knew a fair amount about the Enneagram. I had been reading deeply in Beatrice Chestnut and related subtype material, and I arrived in what I can only describe as a somewhat provocative mood. I stayed at the Apollo Hotel on the canal and walked to the conference each morning. The first person I met was Lynn, a total riot — from San Francisco originally, recently divorced, now running a Kundalini Yoga studio in Athens. She knew everyone and all the back-channel dynamics, who was sleeping with whom, and we bonded instantly. She quickly became my co-conspirator.

The opening talk by Hudson repeated familiar material, including the Desert Fathers, and I came close to challenging him publicly but somehow held back. I do have a big mouth at times. Big dick energy. Then I heard Tom Condon, tall, white-haired, grounded, integrating NLP and Ericksonian ideas into a practical approach. He is the quiet hero of the piece.

The rest of Amsterdam was lively and strange. A movement-based types exercise nearly ended in an accidental kiss. Lunch ran long, as conference lunches always do, and I met people from all over the world. The closing session paired Chestnut’s academic framing with experiential work, including a moment where a participant broke down emotionally on the floor. The atmosphere oscillated between meaningful and chaotic.

At the end, Lynn urged me to ask a provocative question. I did, politely: which aspect of the Enneagram might not be around in thirty years? Chestnut answered cautiously but clearly: tritype — too complicated, not especially helpful. It was a small ripple, but it felt like testing the edges.

That fall, I brought Condon to Tokyo. I was a member of the International Mental Health Professionals Japan (IMPJ), and when I saw he would be in town I arranged a small talk at TELL the night before the conference. About thirty people came. He gave a clear, practical overview. People loved it. Afterward some of us went to the pub; he declined, needing rest for the next day. He was ripping heaters with me outside, though. Legend.

In the end, my curious apprenticeship with the Enneagram left me with more affection than skepticism, even if the skepticism is real. I learned a lot from the system. I still find the types evocative, even poetic, and I still catch myself using them as a loose lens on people and situations. And I genuinely liked the people. The Enneagram world attracts seekers, therapists, wanderers, and enthusiastic amateurs, and I have a real soft spot for that whole vibe — the openness, the fast intimacy, the willingness to experiment. At its best, the community is warm, generous, and human.

But the professional side of the field also felt small, and because it is small, sometimes insular. Limited conferences, limited airtime, gentle pressure toward agreement. Origin stories harden. Pushback is rare. None of this invalidates the system, but it shapes the culture.

By contrast, the astrology world — much larger, more diffuse — feels more pluralistic. Multiple branches coexist. Disagreement is normal. No single group controls the conversation. The atmosphere, in my experience, is looser, less competitive, more comfortable with divergence.

So where does that leave me? Somewhere in the middle, which is probably where I started. The Enneagram, for me, remains personality poetry — suggestive, useful, occasionally illuminating, but not doctrine. My apprenticeship may have been unusual — Singapore hotel lobbies, Minneapolis skyways, Amsterdam provocations, Tokyo workshops, and smoke breaks with Tom — but I wouldn’t trade it. I learned, I laughed, I met memorable people, and I came away with a tool I still sometimes use, lightly. That’s enough.

Dedication:

For Lynn and Tom.