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On My Curious Relationship with the Enneagram

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.

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On Being Early to Shows

Note: Getting to shows early, I realized, isn’t really about beating the crowd but about entering the space before it hardens into an event—when the room is still provisional, the bartender relaxed, the band half-mythical figures moving casually through soundcheck, and the whole night feels less like a performance and more like something forming in real time; you notice the lighting before it matters, the empty floor that will later surge, the stray conversations, the merch table still untouched, and sometimes—if you’re lucky—the musicians themselves, unguarded and human, which subtly rewires the experience so that when the set finally begins you’re not just watching a show but inhabiting a continuum that started hours earlier, a private prelude that rewards patience, sharpens memory, and turns what could have been just another concert into a small, self-contained narrative of anticipation, proximity, and the quiet pleasure of being there before everything becomes official.

Epigraph
“There’s a thin line between a guy with a backstage pass /
and a guy walking around with his gut hanging out like a jackass.”
— Sun Kil Moon, “Ben’s My Friend”

I’ve always been fascinated by the green room. First of all, why green? They can’t all be green. Second, there’s the whole rider situation. The rider is where things get really interesting. I think it was Van Halen who had in their rider that all the brown M&Ms had to be removed from a bowl. This sounds totally bizarre, but the point was attention to detail. If the venue screws up the M&Ms, they might screw up something much more important, like stage rigging or pyrotechnics. The M&Ms were just a test.

Other riders go in different directions. Iggy Pop reportedly asked for things like a Bob Hope impersonator and other surreal odds and ends, more like performance art than hospitality. Meanwhile Beyoncé is famous for highly controlled riders: temperature, lighting, water, environment, everything calibrated. One approach is chaos, the other total control. Both happen in the green room, which most of us never see.

My first concert was Dire Straits in Pullman, Washington, in a big arena. I was nowhere near the green room, of course. Most of us aren’t. So the real question becomes: what happens before the show, if you’re not backstage?

One answer came when I saw They Might Be Giants in Spokane with my friend Kelly Rudd. Kelly told me his cousin was in the opening band. They got paid twenty bucks for the show. The whole band. Twenty dollars. Totally unbelievable. Outta fucking control. TMBG were already a pretty big indie band, “Birdhouse in Your Soul” had been a hit, and I liked “Istanbul (Not Constantinople)” quite a bit. But after hearing that story I never quite looked at them the same way. The green room fantasy took a hit. Backstage wasn’t glamorous. It was twenty bucks and a handshake.

Another time I went to see Cat Power at the old Club Quattro in Osaka. I got there early, of course, and there was an opener dressed like a fairy with fuzzy, messed-up hair who sat down at the piano and proceeded to play dirge after dirge for what felt like an hour. Solo piano can be great, but this was brutal. I honestly thought I might have to cap myself. At some point I checked my ticket just to make sure this wasn’t actually Chan Marshall. It wasn’t. Thank god.

Then Chan came on and instead of playing from the stage like other artists do, she wandered through the crowd with a wireless mic, half-rapping, half-singing, talking, improvising. It wasn’t really a concert. It was more like some kind of performance art happening. Totally outta control. If I’d come late I would have missed the whole bizarre prelude. Being early meant enduring the dirges but also getting the full weirdness of the night.

Another early-arriver adventure came when I saw Deerhunter at the Hostess Club Weekender. These shows started early and stacked openers all day long. I once saw Mogwai at one of these and had to leave after fifteen minutes because I was hungry, tired, faded, and they were boring the living shit out of me. It happens.

The Deerhunter show in Osaka was even more outta control. The headliner was scheduled for 7 PM, but there were something like six openers. One of them was Ivo Watts-Russell of 4AD, a legendary figure, but he droned on so long that by the time Deerhunter came on they only had about forty minutes. Bradford Cox introduced him with dripping sarcasm, emphasizing “LABEL BOSS,” clearly taking the piss because the band’s time had been cut. I ended up having to see them again months later in Nagoya to get the full set. That’s the risk of being early: sometimes the openers eat the show.

The flip side came when I saw The Hold Steady at the Brooklyn Bowl in December 2018. I arrived two hours early, ate a hamburger, and smoked up outside. That’s where I met Austin, a total Steadyhead. He knew everything: lineups, labels, deep cuts, all of it. We talked music, smoked, and waited. When doors opened we grabbed territory near the stage with the other early-arrivers, a semi-cliquey group of diehards.

Later, when Austin wanted to get back to the front for the encore, he told me to follow him. He moved through the crowd at a half jog and the people parted in front of him like he was Barry Sanders hitting holes. Seconds later we were hugging the stage. I knew then I was in the presence of greatness. I also knew he was my friend. I didn’t get the VIP meet and greet, but getting there early gave me something better.

My one true VIP experience came when I saw The Afghan Whigs in Amsterdam in 2017 at the Paradiso Amsterdam, a beautiful converted church. I arrived three hours early, met Greg Dulli and the band, took photos, bought merch, and watched soundcheck with maybe fifteen people. They played “Going to Town” acoustically, which was a revelation. Later they crushed the full electric set, ending with “Faded.” I paid fifty bucks for that meet and greet and it was completely worth it. Being early paid off directly.

Getting to shows early, then, is not really about the green room at all. The green room is a kind of fantasy—green walls, bowls of M&Ms, riders with impossible demands. Most of us never see it, and even when we do, it turns out to be smaller and more ordinary than imagined. And probably not even green. The real action happens in that strange in-between space before the show: the smoking area, the empty floor, the long wait while the openers drift on and off.

If you arrive early, you get all of it. You get the terrible fairy-piano dirges and the label boss who drones on too long. You get the moment of doubt when you check your ticket and wonder if this could possibly be the headliner. You get the rail territory battles and the cliquey early crew. You get the conversations with strangers who turn into temporary friends, like Austin, who parts the crowd like a halfback and gets you back to the stage in seconds. You get the soundcheck if you’re lucky, the acoustic revelation, the quiet before the storm.

Most of all, you get time. And time at a show is a funny thing. Once the lights go down, everything compresses. The band plays, the songs blur together, and before you know it the encore hits and everyone spills out into the night. But if you were there early, the show feels bigger. It has a beginning, a middle, and an end. You saw the room empty and then full. You watched the night assemble itself.

So while some people drift in late, grab a drink, and wait for the headliner, I’ve always preferred the long route. Get there early. Kill time. Smoke a cigarette. Talk to whoever’s around. Endure the openers, good or bad. Maybe you meet someone. Maybe you don’t. Maybe the band walks through the room. Maybe nothing happens at all. But every once in a while, if you’re lucky, something does. And that, in the end, is why I like to be early to shows.

Dedication:

For music lovers everywhere. You are my tribe baby.

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On My Dad’s Ridiculous Climbing Strategies

Note: This is a new piece about my dad, Ross Thomas (RO), and his truly unbelievable climbing strategies. The central episode took place in Stehekin, Washington, many years ago, when RO led my brothers and me on an attempt to reach Castle Rock that quickly devolved into heat, dense forest, no water, and general mayhem. There is also a later coda involving a climbing gym in Portland that is, in its own way, even more outta control. This piece is comic in nature, but also affectionate. My dad is a great man, a brave man, and a very game climber. He is just not, in this one specific domain, a planner.

Send lawyers, guns and money — the shit has hit the fan
— Warren Zevon, refracted

RO, is a great man and a terrible climbing strategist. He is brave, energetic, physically game, and in most areas of life basically well organized. He was a good high school English teacher, a very good administrator, and for many years an excellent and meticulous girls’ basketball coach. He is not, in other words, some kind of general life-space incompetent. Quite the opposite. Which is what makes his climbing strategies so difficult to understand.

They are ridiculous. They are unbelievable. They are officially, historically, and totally outta control.

I say this with love.

The central case study here took place in the mid-2000s, let’s say 2005, when our family was staying in Stehekin, Washington, out on Lake Chelan. If you have never been to Stehekin, it is a beautiful and slightly improbable place, the kind of place that already feels like the beginning of a story. Lake Chelan is huge, and you get out there by ferry, which means from the jump there is a sense that you are committing to something. People camp there or stay in cabins. We were in a cabin. My mom Claudia (CL), stayed behind. RO, meanwhile, had a plan.

The plan was that RO and his sons — Mike (MI), Pat (PA), and me — would hike up toward Castle Rock.

Now, one thing about family expeditions is that “the plan” is often not really a collective possession. It belongs to one person. The rest of the group is more or less there to follow along. In this case, the plan belonged entirely to RO. MI and PA and I were, broadly speaking, along for the ride.

As I remember it, we started from Stehekin and walked about three miles just to get to the trailhead, then hiked a few more hours uptrail to where we stopped and camped the first night. It was already a decent undertaking just to get there, but this was, in a sense, merely the prelude. The true RO strategy had not yet fully revealed itself.

At around dusk, after we got to camp and set up the tent and got ourselves sorted for dinner, RO decided he was going to scout the route for the next day. This seemed reasonable enough. It is in fact the sort of thing a prudent leader might do. Only instead of scouting further up the trail, or perhaps generally uphill toward the place we were trying to go, RO for some reason headed downriver.

Why did he do this? We did not know. It was back downhill. It seemed unrelated to the objective. Even at the time it had the feel of one of those decisions that makes perfect sense only to the person making it.

Ross Thomas: The trail kind of petered out eventually and didn’t really lead to Castle Rock anyway.

Fair enough. I want RO’s side of the record included here. But even granting this, and I do grant it, going downriver in the late evening did not strike the rest of us as a strong opening move.

Sure enough, RO fell in the river and got completely soaked.

This was the first of many mistakes he would make on the trip.

He came back to camp late and dripping wet, having apparently developed an immediate a bizarre attachment to that river. The water was cold. The evening was cool. He changed clothes, we had dinner, and we went to bed. At this point, there was still some chance that the next day might somehow become normal.

It did not.

The next morning we got up early, had breakfast, and prepared to head out. My assumption — based on reason, precedent, and the literal existence of trails — was that we would continue on the trail. Instead, RO decided that we were going to bushwhack straight uphill through an extremely dense forest in the blazing heat.

This struck me as a bad plan.

It was a bad plan.

The forest was thick enough that you could not really move with any rhythm. We were not hiking so much as negotiating, arguing, and physically contesting with the landscape. Every movement took extra energy. Progress was incredibly slow. The heat was serious. And the main problem, which quickly became the only problem, was that there was no water. Not a stream. Not a trickle. Not a suspicious puddle. Nothing.

Now, RO for reasons that remain mysterious to me is not a big water drinker. He prefers beer and tea. Under ordinary conditions this is merely a personality trait. On a hot uphill bushwhack through dense forest it becomes a strategic liability.

Naturally, we asked where the water was.

Ross Thomas: I had read in a Fred Beckey book that there was a way to get up to Castle Rock, although I think Beckey had only heard about it and never actually done it himself.

This is, in its way, a perfect Ross Thomas detail. Fred Beckey, the legendary climber, had perhaps heard there was some route, though he had not personally taken it. This was enough for RO. A rumor in a book by a famous climber became an operating plan.

As for the water situation, RO told us — and I remember this vividly — that there might be some in about five miles.

Five miles!!!

We were already fighting for our lives up there, and this crazy man was calmly informing us that in only another five miles there might, possibly, perhaps, be water.

He’s totally outta control.

At some point, after what I recall as roughly three miles of this lunacy, we basically mutinied. Or perhaps mutiny is too strong; let’s call it collective realism. We told RO the obvious, which was that this was not going to work. The route was no good. The heat was too much. There was no water. We had to turn back.

And so we did.

Now the descent was interesting because it brought out our distinct styles. RO, MI, and PA were making their way down carefully, gingerly, responsibly. I, on the other hand, was absolutely flying. Swinging from tree to tree like some kind of deranged monkey, just ripping downhill through the forest. This part RO loves to tell to this day, and I admit it was one of my better athletic showings. I was not going to die of thirst in that forest and I was not going to descend politely either.

Eventually we made it back to camp. Or rather, most of us made it back to camp together. RO, in one of those small but meaningful complications that tend to gather around him in climbing situations, got separated from us and somehow ended up down by the river again.

And yes, he fell in again.

He really must have loved that river.

So now here he comes back to camp once more, drenched, and by this point we are all in total agreement that the trip is over. We are done. It is time to 86 the hell out of there.

So we break camp and head down toward the lake shore. But this presents a new problem. We still have a significant walk to get home — something like another two miles down to the shore and then, as I remember it, another three miles around the lake. And by now it is dusk. So this is not really viable either. We are hot, tired, and in no mood for an elegant final act.

At this point RO does what he often does in these situations, which is simply assume that reality will provide.

He found a guy with a motorboat and asked if he would take us back to Stehekin.

The guy said sure. Fifty bucks.

RO then informed him that he did not actually have fifty dollars on him, but could get it from his wife once we got back to the cabin.

Somehow, by what can only be described as grace, audacity, or a temporary breakdown in the boatman’s judgment, this worked. We got in the boat, got home safely, and made it back in time for dinner.

That was Stehekin.

CODA

You might think the lesson here would have been: bring water, stick to trails, do not base wilderness plans on rumor, avoid rivers if possible, and maybe do not lead your sons into dense forests in the hot sun in search of a semi-mythical route described secondhand by Fred Beckey.

You would be mistaken.

Many years later, when RO was Principal of Valley Catholic High School, he got really into climbing at a gym in Portland. It is a cool place, run by a father and son, and it has beginner, intermediate, and advanced climbs. He took me and MI and PA there, and later my son Hugh as well. Hugh loved it. He scampered up the walls like he had been waiting for exactly this sort of thing his whole life. I like climbing too, though my arms get tired pretty quickly and I tend to fade. MI and PA are both good climbers. RO, to his credit, also has strong stamina.

So one day my wife and Hugh and I were there with him. We’d been climbing for a few hours. I was on the mats, faded, taking a break. Hugh was still going. RO was showing him some moves. Then RO started up one of the big walls — one of the long climbs, the kind where you need the harness.

Only he had forgotten to put the harness on.

Hugh saw this before anyone else did and yelled out:

RO, get down now!

And RO did.

For the next year, RO loved telling the story of how Hugh had saved his life. Quite right too. It is a great story. My son saved my dad from one of my dad’s own ridiculous climbing strategies. The circle was complete.

But then, about a year later, shortly before RO retired from the principal job in 2018, he was back at the gym by himself. This time the only other people there were the owner and his son. And somehow — incredibly, impossibly, yet also in a way entirely consistently with the established Ross Thomas climbing tradition — he forgot the harness again, started up the big wall, and fell.

He crashed all the way down onto the mat.

The mat saved his life, no question. But his feet and knees and legs got absolutely busted up. He was in a wheelchair for months. It was so bad that he had to move temporarily out of the country house in the woods where he lives with CL and into a little bungalow on the Valley Catholic campus owned by the nuns that founded and still run the school. He could barely work. To this day his feet remain a total mess. He has trouble driving and has to drive with his shoes off and wearing some sort of thick sock or something.

At one point we wondered whether he might sue the gym owner for negligence. But RO wanted no part of that. He said it was his own fault, not the owner’s.

Fair enough.

And then, after many months, he mostly recovered. Which means this story has, if not exactly a happy ending, at least a decent one. Better still, as soon as he was recovered he went right back to the gym and started climbing again!

This is what I mean.

His climbing strategies are ridiculous. They are unbelievable. They are officially, historically, and totally outta control. He does not plan for basic things such as the route, the water, or how exactly one might avoid miles of dense forest. He does not always remember the harness. He seems, in climbing situations, to operate according to a distinct internal logic unavailable to the rest of us.

And yet outside of climbing, this makes almost no sense. He is, as I said, a basically well-organized guy. He planned lessons. He coached meticulously. He ran a school. In most areas of life he is not slapdash at all. Which makes the climbing thing not just reckless but anomalous. It is a localized mystery. A glitch in an otherwise coherent system. I do not understand it and at this point I do not expect to.

What I do know is this: to this day I avoid climbing with him because in this one particular area I do not trust his judgment at all.

I love the man. But when it comes to climbing, he is not to be trusted.

Dedication:

For my dad. I love you baby but you are totally outta control.