A Brief Personal Introduction to the Enneagram

The first in a series of posts about my favorite personality test

Here is the life story of nearly everyone.

You are born into a hostile, uncertain world. If you’re lucky, at first, things are pretty cozy when you’re a baby. But you’re hardly aware of that—all you know is the sharp pang of uncomplicated needs, followed by their resolution. Mostly you’re aware of an undifferentiated fuzz, cooing noises, the touch of your loved ones. 

Following this, though, the inception of your maturing awareness, unfortunately, corresponds with the disruption of your coziness. Around the time it becomes clear that there are other minds, it’s also clear that the owners of those minds can dislike you, ostracize you, deny you cake, etcetera. Your behavior becomes motivated, primarily, by maintaining safety, comfort, abundance, tasty food. You become a social being.

As you test out the properties of this new existence, you notice that certain behaviors work well for you. Like if you do certain things you get food love etcetera. Your most reliably rewarded behaviors are those that fit into your natural aptitudes well while also being socially acceptable. Those become the basis of your social acceptance strategy, which is to say, your personality. (You don’t really notice that this is happening, this happens all by itself.) This lumps up and hardens and becomes your life. 

Maybe you’re loyal and play well with groups—so your strategy is being a good follower, soldier, citizen, etc. Maybe you’re disputative and competitive—so you’re a debate club kid, later a KPMG consultant who tells people they’re wrong for a living.

These behavioral structures are your virtues. But they are also your limitations, and your compulsions, forming your dysfunction when stuff gets ugly. Like if you’re a helper-type person, your warmth and generosity can sour if you enter into asymmetrical relationships with people who take advantage of your giving personality. If you’re a melancholy poet type, your life can devolve into a series of temper tantrums where you make yourself difficult to understand, and then lament your loneliness. A lot of this, again, you don’t notice, it’s just your default, the lens through which you see the world. 

At a certain point, life becomes complicated, so your normal strategy breaks down. Perhaps you’ve spent your life in the realms of the intellect, but you realize that you’re lost when it comes to matters of the heart, suddenly it turns out you have no idea how to connect with your wife. Or you’re a chameleonic perfectionist, able to see and match the expectations of others, but you realize you haven’t actually developed any inner worth, and you’re miserable when success becomes monotonous, or unavailable. Or you’re an artist whom a particular muse breaks up with, and you have to find a new act to perform.

Then—usually not before—is the time when you grow. You see your destructive cycles fully, once robbed of the rewards that kept them going. You understand your foibles. You evolve both by strengthening your core virtues and understanding how they can’t compose the whole of life. In the end, the shape of your personality remains, but it doesn’t entrap you.

This is the story that the Enneagram tells. As far as impossibly overgeneralized stories about human development go, it’s a pretty good one.

Unlike other personality systems, which seem to exist to tell you how you’re special, the Enneagram is there to tell you how you’re sick. Each type centers around a fatal flaw that’s also virtue. The basic Enneagram formula, as related by superstar Franciscan Enneagram specialist Richard Rohr, is that you are “ruined by your gift.” This nicely captures an elusive difficulty of personal growth: ironically, the tendencies you want to work on are inextricably locked into the patterns of behavior you’re rewarded for—they’re part of the deep patterns of you. 

Here’s how it helped me.

To those who know the Enneagram and know me, I’m extremely easy to peg. I’m a 7, the enthusiast. We are great. We are also so fucking annoying. We are the eternal children: full of life and optimism and energy, endlessly social, able to lend buoyancy to even the most devastating circumstances, the people who are willing to play our piccolos into the lingering smoke of recent artillery fire. However, we can also be total flakes, fleeing any discomfort, using people for temporary emotional affirmation, and then disappearing at the sight of trouble. At worst, we are addicts looking for respite when even the briefest of pains becomes too much to take, like Mayakovsky shooting himself in the heart after none of his friends answered his frenzied phone calls.

But this was never obvious to me, because, from the outside, I was always doing difficult things. Like dropping out of college to write a novel. Or traveling to Asia at the drop of a hat and reconstituting my life there. Or writing a book about my sorrows and failures. Or starting a successful business.

What I didn’t notice were the commonalities there. Everything involved, sure, an enviable amount of optimism and brio. But I was always fleeing as I was flying. College got shitty, time to do something else. Toronto was filled with relationships I’d wrecked with my avoidant tendencies, time to ‘reinvent myself.’ And even the difficult things I did had air of chattiness and shallowness to them. My book is emotional, but it also flits between emotions willy-nilly, which is both a strength and a weakness—it’s a fun reading experience but it could be more substantial. 

I didn’t see any of this, really, before stumbling on the Enneagram. I saw it at moments, but then I, uh, fled from that knowledge. And, crucially, I didn’t see it as a flaw inextricably linked to my strengths, so when I perceived my flightiness, I thought of it as something I had to deny and be ashamed of, rather than harness, embrace, and reform.

And then I stumbled on this Richard Rohr video somehow. Don’t remember how. The algorithm just served it up to me somehow. (We remember the litany of The Last Psychiatrist: if you’re seeing it, it’s for you.) Even though the video was littered with Christian references that are not my vernacular, it captivated me. Every ten minutes, Rohr casually lobbed an unmistakable lightning bolt of spiritual/psychological truth. And then I picked up his Enneagram book, and, within a short interval, I realized what I was, because the section on 7s made me say “oh no” out loud repeatedly. Here are two of the passages that made me blush:

Sevens are not specialists, but “generalists.” They always have several irons in the fire, because they always want to leave all their options open and unconsciously want to avoid committing themselves too deeply to a thing or a person. In depth they always see pain lurking for them. Besides, if you totally devote yourself to someone or something your own limits might become visible—and that too would be painful. Thus many Sevens master the art of bluffing; they are all-around dilettantes and evoke the impression of being many-faceted in their gifts, of knowing all about everything. A handful of facts, cleverly combined, sometimes suffice to create a comprehensive image.

…

Many sevens talk too much, just as they are inclined to do everything “too much.” They have to work to become more “sober” and ascetic in every way. When Sevens let someone offer them pastoral counseling, it should run like this: “If you think you have to talk this much, cut it in half. If you think you want to drink this much, half is still too much. If you think you need all these free-time activities, cross out every other one.” Less is always more when an immature seven wants to be liberated from themselves.

Like anyone sensible, my view is that personality tests are somewhat bullshit while also being entirely real. Everyone who’s been around has observed that there are genres of people. Archetypes of society are real, too: the simpering vizier whispering to the sultan, the quietly desperate corporate cog mumbling unwritten odes, etcetera. And if you clump people together based on their answers to a battery of questions, you’ll probably capture some of those genres. By crystallizing the patterns of yourself and others, you can have some handles that make it easier to discuss the vagaries of human personality.

I don’t have a scientifically defensible reason for liking the Enneagram more than the other personality tests in fashion. I just like it because its talons sunk into my heart. When I was so embarrassingly pegged as a type of guy by that book, for the first time, I earnestly asked the question: what if I actually stuck with things that were hard? And the follow-on question: would I literally die if I didn’t shrink from negative emotions? The answers to those queries have lead to a new level of depth in my waking existence.

But I also like the Enneagram for other reasons. Apparently it gives me psychic powers.

Here’s a thing that happens in my coaching practice fairly often. I meet with a client who tells me about their difficulties in expressing themselves. And, if I’m pretty confident of their Enneagram type—which is not always true, by the way—I say something like, “cool. Tell me if I’m wrong, but I have a suspicion that this might connect to [some variety of emotional difficulty I’d predict they might have based on their type.] Is that bullshit, or not?”

Sometimes I explicitly mention the Enneagram in these conversations, sometimes I don’t. Either way, the results are typically good—as in, I’m not exactly right, but I’m pointing at something valid—or I’ve eerily nailed an emotional pattern that the client has never seen before. One client, in such a moment, asked me if I was a magician. I am not a magician, I just read a couple of Enneagram books. And, to be fair, sometimes I’m totally incorrect, but this is actually uncommon.

If I’ve convinced you that the Enneagram is worth looking into, then you are now in the right place to receive a stream of relevant information. In the next few posts, I’m going to share some personal reflections on the different Enneagram types and how I think about relating to them. This will give you a flavor of how the framework helps me understand people.

If, though, after reading this introduction, you think the Enneagram is a bunch of bullshit that you don’t care about, then I suggest not reading the next 3 editions of this newsletter. I will try to avoid diagnosing what personality type would cause you to behave in such a fashion.