The Enneagram Is Not Magic

Click above to listen to the author reading this piece.

“I’m a ten,” my client jokes, and crosses his arms before adding, almost apologetically: “I don’t do stuff like this; it’s a little, you know, ‘woo-woo,’ for me.” His colleagues chuckle, and I smile.

I’ve heard this one before.

The poor man doesn’t want to pick an Enneagram type. He’s a finance guy. He’s never entertained the kinds of questions I’m asking him, and probably hasn’t spent much time wondering: Why do I do what I do? But, like it or not, he doesn’t have much choice because his boss hired me to teach his team the Enneagram, and now we’re in it.

I thank him for his honesty and ask what the test said. He doesn’t remember but makes an effort to retrieve the Enneagram test results on his phone.

“It said Type Six and Eight,” he dutifully reports to his team and me. “I could see something in both of them, but neither one is fully me. Maybe 60 percent,” he says doubtfully.

I’m an Enneagram facilitator, and luckily, I love people. The Enneagram is a psychological system. It identifies the repeating patterns of thinking, feeling, and behavior that we call personality. My job is to help everyone in the room discern which personality type is running them so they can work with their unconscious habits. I’m not deterred by the man in front of me, just the opposite. Actually, he’s given me a lot to work with.

By now, I can feel that he’s defensive and a little skeptical, but also, there’s a willingness about him. He wants more certainty, and isn’t finding it yet. He’s also not afraid to say what’s on his mind. The first type on his list, Type Six, is called—wait for it: the Loyal Skeptic. He could be another type, but given the givens, I’m gonna put my money on Six.

“Well,” I tell him, “Sixes are pretty intuitive. When they’re present, Sixes know if something’s bullshit, that’s for sure.” He cocks his head to the side, trying to figure out what to make of me and what I’m saying. It feels like his mind is open.

“Can I ask you a few questions?” I say.

“Sure,” he says, leaning forward, elbows on his knees, as if ready for an interrogation.

“How easy is it for you to trust?” I start.

“It depends.” He says, leaning back.

“On what?” I ask him.

He hesitates. “Do you mean people? It depends on the person. Or, do you mean situations? It depends on the circumstances, and what’s going on for me.” I nod, not disagreeing with him.

“How easy is it for you to trust yourself?” I ask.

“I trust but verify,” he says slowly, smiling. It’s impossible not to like this guy. “I like to think things through,” he says. Of course he does.

“And, why is that?” I wonder out loud.

“I don’t know,” he says, a little too quickly.

“Well, make it up,” I encourage him, gently shrugging. He doesn’t know that I’ve borrowed this line from another Six, one of my first Enneagram teachers, Dr. David Daniels. David’s son was my mentor, and also a Type Six. The two of them really impressed upon me the importance of understanding not just what we do, but why.

“Well, sometimes people aren’t trustworthy,” he informs us.

“Right,” I agree, appreciating how, in his mind, they’re not necessarily.

I move on. “How important is safety to you?”

“Very.” He doesn’t hesitate with that question.

“And, why is that?” I ask him.

“I don’t know, it just is,” my client says, as if I just asked him why breathing was important. He’s looking around, probably wondering if anyone else is questioning all this “woo-woo” stuff. He looks back at me. I know that what Sixes want most is to know who or what they can trust. So, I’m working hard on my end not to tell him what he thinks.

His colleague jumps in. “He’s the Chief Safety Officer; he always worries about liability and our policies. He watches out for the whole organization,” she says helpfully. Sixes are often beloved, and I can see that he is.

I thank his colleague and look back at our Six. “Is this true about you?”

“I do watch our exposure. That’s part of my job,” he says, keeping to the facts.

“And you’re good at it.” I offer it as a half-statement, half-question. He looks mildly uncomfortable. “They haven’t fired me, yet,” he quips, with a raised eyebrow.

Knowing Sixes operate better with information, I decide to offer him some. “Type Six comes to teach the rest of us to wake up and pay attention to what’s going on,” I begin. “I’m not saying Sixes are psychic, but they have a sixth sense, an innate kind of knowing. It’s their superpower. This makes Sixes great team players and leaders because they’re alert and dare to ask the hard questions. Sixes start to worry when other people aren’t worrying about the same things.

“Hm,” he says, still noncommittal but clearly thinking about what I’m telling him. I continue, trusting the Enneagram enough for both of us.

“Sixes filter the world through their mind. They’re one of the ‘head types’ who get their information through what we call the ‘cognitive center of intelligence.’ Other types rely on their gut or heart. Head types want facts. They want to know whether their information is congruent with what others have said or done. Sixes think in future terms. When things don’t add up, they’re the ones who call it out.”

I pause and am about to check in with our Six, when his colleague chimes in again, “That’s totally him, he triple checks and verifies,” she tells me. I’m not ruling out Type Two, the Helper for her. It can be helpful to know how other people perceive us, of course, but what really counts is how we see ourselves. Our Six still looks puzzled.

I offer him a little more information. “Type Sixes are analytical and strategic; they get hired for their ability to think critically.”

“Interesting,” he says.

“But, here’s the deal,” I say, wanting to keep it honest, “Every type is afraid of something, and the ‘Basic Fear’ for Type Six is of having no support. The crazy-making part of personality is that we start to feel like we are not enough of what we essentially are.”

I pause, letting this land.

“Sixes are so supportive. They’re trustworthy, they’re devoted, and loyal,” I continue, “but (unconsciously) they come from a place of alarm, doubt—fear, actually. They see the world as untrustworthy and unpredictable; it’s a projection. Sixes can get trapped in a mental prison of worry and doubt, projecting their lack of self-trust onto everyone and everything.”

Shaking his head, the man says, “Yeah, man, that does sound like me.” God, I love the Six. He can’t help himself. If something is real and true, Sixes are there. I’m hopeful that he can stay with his doubtful mind a little longer. No amount of information can match the power of trusting oneself.

The most difficult part of learning the Enneagram is not the Enneagram; it’s seeing ourselves clearly. Along the way, we run into our habituated thinking, our biases, and assumptions. Personality is riddled with these unconscious parts of our human nature. There are many look-alikes among the nine Enneagram types, for good reasons. There’s always a pattern.

The most difficult part of learning the Enneagram is not the Enneagram; it’s seeing ourselves clearly.

Take types Four, Six, and Eight, which look very similar to each other at first blush. Russ Hudson, another one of my mentors, coined a term for these three types—he calls them the “Truth Tellers.” I am not surprised that Eight is second on my client’s list. All three Truth Tellers want to keep it real and often say provocative, daring things, for different reasons. Fours are driven by a deep desire for connection, Eights for control, and Sixes for safety. Our centers let us know what alarm system we are driven by: fear, anger, or grief. I think a lot of people get confused when choosing their type because they’re not used to tolerating those big emotions or to observing themselves in this way (see my posts about this HERE and HERE).

That’s basically what personality is: a way to avoid the parts of us that are afraid, angry, or sad. Most people stop at the first signs of discomfort. Studying personality ought to be uncomfortable; it’s about our unconscious, not who we are, but who we take ourselves to be. I think many of us have done our fair share of pretending, but there’s a real reckoning with the truth going on lately, as you might’ve noticed.

If you’ve encountered something about your personality that you don’t like, good news—it’s not really you, it’s your ego. People are essentially good, loving, honest, real, joyful, and I could go on. It’s the distortion of these essentially positive things, aka personality, which we feel icky about. So, you found something you don’t “resonate with,” maybe you’re not in the accurate Enneagram type yet. Or, maybe you have stumbled across something that has been hiding out in your unconscious.

Whenever we encounter these uncomfortable things, the very next question is, can you keep your mind and heart open long enough to feel the difference between who you are (your essence) and your habituated unconscious (your ego)? I’m not suggesting this is easy; not at all. That’s why we call it “The Work.” I’ve spent the majority of my career empowering people to use the Enneagram to navigate the prisons of our minds. Some of my best teachers are those who live behind actual bars. When I’m not teaching the Enneagram in corporations, I work for a nonprofit called the Enneagram Prison Project, which I founded in 2012.

People on corporate teams are fascinated by the work we do in prison when they hear about it. Once someone feels how vulnerable it is to grapple with ego openly with their team or partners, they wonder how that could possibly happen in a prison setting. Often, clients ask me how I get “those people” to open up about themselves. I lean in conspiratorially, “Do you know who the most difficult people are to teach?” I love to ask.

“Who?” They always want to know.

“Us ‘free’ folks!” I break it to them. Out here, we have more things to hide behind: titles, salaries, families, and status. On the “inside,” most people have already lost so much: their dignity, possessions, and, of course, their freedom. By the time someone finds their way into our self-awareness training, they’ve had some degree of acceptance that whatever they were doing isn’t “working” for them; it’s gotten them into a lot of trouble. In some ways, students who take our course in prison have more agency than my clients, like our Six, who was held hostage through the training due to his employment.

Whether in corporate work or in-custody, that tiny edge of “free choice” goes a long way when working with people navigating their egos. Even being a so-called Truth Teller, however, does not guarantee that we are telling ourselves the whole truth. I had a Type Eight in my class at San Quentin who was a Hell’s Angel, back in his day. He still looks every bit the part. I’ll call him “Mac” to protect his identity. Mac is a huge man, bald, bearded, tatted up, and gruff. I liked him, instantly. Unlike our Six, he had no hesitation owning his personality, type Eight, which we call the Boss, or Protector. Eights come to teach the rest of us about aliveness and vulnerability, and boy, did he do both.

In the many decades since he’d “been down,” Mac had never taken a program like the one offered by Enneagram Prison Project, where the invitation is to share about feelings and the things that happened in childhood. On the first day of class, Mac told us, “I don’t do things like this.” Sound familiar? At the end of the first day, Mac told us, “I don’t think I’ll be back.”

“Okay,” we said.

The next week, there he was, back in his same seat. Mac is as Eight as they come, with all of the characteristics: confident, loud, brazen. He also has a sweetness about him, like a big teddy bear inside—a wonderful quality of Eights, who get the message that they have to be strong when they’re little. Eights carry this impression around, bullying bullies, and standing up to injustices, rejecting vulnerability and the possibility that anyone would stand up for them. Everyone has a fear, and the Basic Fear for the Eight is of being harmed or controlled.

Week after week, Mac sat listening intently, his big forearms folded over his belly. At the end of every class, we said, “See you next week, Mac,” and each week he said something like, “I doubt it,” over his shoulder as he walked out. He showed up to every class, almost like he couldn’t turn away. Mac sat on a panel with other type Eights in the classroom, during which he shared about growing up in “the Club,” as he called it, and shocked us with Angels lore. He even wrote a childhood biography, which is a brave assignment. I saw Mac while walking through “the yard” one afternoon. He was there, with his shirt off, soaking up the sun with his boys, and he waved me over to say hello, which I did, gladly. We “chopped it up” together, as they say. As the weeks went on, I felt a growing affection for Mac, but also could tell he didn’t quite let his guard down, at least not with me. It felt like he had a lot in reserve.

On graduation day, we had a large gathering of about 100 people, including past graduates and guests from outside. As people arrived, I sat next to Mac for a moment and asked him, “Hey, what was this class like for you?” Then, he came clean. “You know, I don’t know why I took this class. Even today, I turned around halfway here thinking I just wasn’t gonna come. I still don’t even know why I did,” he said, struggling to find his words. Then suddenly out they came. “You know, I don’t think everyone in here is a hundred percent honest. I don’t think YOU’RE a hundred percent!” he exclaimed. “God, I’ve been wanting to say that to you!” he breathed out, visibly relieved. I was relieved, too.

There it finally was, the truth.

I appreciated him for saying it, and I meant it. “You know, I think you’re right,” I told him. “As you say that, I’m thinking, I don’t think any of us are being 100% honest with ourselves. Even on a good day, I’m half hiding behind my personality, being ‘too nice,’ or not saying the thing I really want to say. I have all kinds of observations about people that I don’t share. It’s not easy to figure out just how honest to be in here. Personality is not easy to navigate.”

Mac looked back at me. Then, he repeated his relief at finally getting “this huge weight” off his chest, all over again. I let him get it all out and worked to stay extra present to Mac, being real with me. When he was done, I took a breath and said to him, “Can I tell you something?”

“Sure, yeah, anything,” he told me, now more receptive than I’d felt he was in the entire twelve weeks we’d just spent together.

“I don’t think you’re a hundred percent either,” I told him slowly but as directly as I could muster. He looked back at me the way every Eight I’ve ever known does—directly, in an unflinching gaze that’s pretty intense. For years, I have practiced not looking away from that kind of intensity or the truthful words that preceded his gaze. I waited several seconds before adding, “You have a big persona,” I told him. “You’re one tough dude; anyone can see it. But it’s a cover. There’s a really sweet guy inside of you that you hardly ever let out, because I bet a part of you is terrified of what’ll happen to him. I get it, Mac. I do. None of us is 100 percent; that’s why I love coming in here and giving it another go, week after week. I’m glad I got to work with you, and I like how you put it.”

Mac looked right back at me and smiled, “Yeah, I guess you’re right.” He said. And that was that.

No one is above our bad behavior or egoic moments. All of us have the capacity to show up as our high side or our low side. The Enneagram is not just a horizontal system that describes patterns; it accounts for our level of development, like a metric of what percentage of honesty we’re willing to show up with. The Enneagram is not Magic, and I’m no magician, but there is a kind of mystery that permeates this psychological tool when we stick with it and ourselves long enough to see what truths it wants to reveal.

Don’t know your Enneagram type?

Take an Enneagram TEST

Still not sure?

Type Exploration

Are you interested in seeing how The Work works without a huge commitment? We have two new offerings for you.

Monthly Drop-In Series: On Being in Relationship

We are dropping in with one Enneagram type each month to feel what it’s like to be in relationship with them. In the month of March, it’s On Being In Relationship

with Type One, the “Idealist.” Thursday, March 26, from 5 - 6:30 pm PT. Sessions are on Zoom and facilitated by yours truly. You don’t need to know anything to come, and it will likely feel supportive if you can pick an Enneagram type.

Drop In with Type 1

COMING SOON! Mini Course: 9 Faces of Potential

A self-guided trip around the Enneagram where we share our compassionate approach to the Enneagram. You can go and grow at your own pace. Available mid-April. Watch this space.