What I Do with The Enneagram

My plan was to write this week’s essay during my upcoming flight.

But upon waking this morning, I remembered that I had absolutely no intention of packing my computer for this trip. So, instead of coming to you from the ‘friendly skies’ mid-day on Monday, it is Saturday morning. I am still in my jammies, my glasses are on— and in truth, I’m perfectly content to write on a weekend so that I don’t have to drag a machine and chords to California.

I am embarking on a week-long Enneagram retreat that I have been looking forward to for months.

On Monday, I travel. Tuesday through Saturday, I have all-day sessions with the group assembled. Saturday night, I take a red-eye back home. Sunday, I sleep.

It occurred to me I haven’t talked about the Enneagram much yet, so this week feels like the perfect opportunity to share why and how the Enneagram fits into my life, my inner growth, and my work vocation to move us closer to racial and gender justice in our lifetime.

Before I go any further, I want to recognize that I am aware that the Enneagram has gained public attention in recent years. With that comes many opinions, and even folks knowingly or unknowingly who distort the tool and then give it a bad name.

In my experience, this often happens when an author, tool, book, or framework reaches a large scale. In America, in particular, we are often taught to hope for a silver bullet – a winning lottery ticket, a magic pill, some one thing that we can tie ourselves to and hang on for dear life. The Enneagram is not my everything. It’s one of my many things.

So, if you come to this essay skeptical of the Enneagram or with a bunch of preconceived notions about it despite never having studied it yourself, I totally get that. I will offer you the wisdom I gained in Al-Anon: “Take what you like, and leave the rest.”

One of the reasons I feel so comfortable talking about tools and sharing them with others is that I do NOT subscribe to one-size-fits-all-thinking. I do NOT blindly follow singular gurus. I do NOT think there is only one right path.

Instead, I look to tools for deepened self-awareness and weave them together in a value-aligned, goal-directed, free, and complex way, not prescriptive and black and white.

How did the Enneagram come into my life?

I’m glad you asked ;)

Picture it…Sicily…1910…Just kidding. I do find the Golden Girls format of storytelling helpful though, so I’ll stick with it.

Picture it: forested foothills in Maryland, spring of 2009. I was part of a team of professional community and political organizers, roughly a dozen of us, and we had just got our asses kicked in the November 2008 election.

We had lost Proposition 8.

We fought like hell for years to defeat an anti-gay opposition, but voters went to the polls that day and voted for Barak Obama, voted for the use of medical marijuana, voted against a shitty parental consent abortion restriction, and still decided…….”nah, gay people getting married sounds too gross.”

It was devastating.

We had tried – hard.

We were tired – like bone and soul tired.

And we were getting ready to be deployed to next states (for me that would turn out to be Maine and New Jersey), and we have the benefit of hindsight now to know that the wave of marriage wins in 2012 was still 4 tough years ahead.

My team and I were battle-scarred (I say that with no disrespect to veterans). Psychologically, our experiences would qualify as traumatic. We were yelled at, threatened, demeaned, dehumanized, and bullied. It was gross. It was incremental. And in some ways, it felt like death by a thousand papercuts.

So, the Enneagram.

THANK GOD I was reared in a sliver of the progressive movement that called on and listened to our lesbian elders. These incredible freedom-fighting women were the folks who showed up and sat at the bedsides of the dying during the AIDS pandemic. These women forged paths for gender liberation, women in the workforce, alternative family constellations, and more.

For my team, a few months after that fateful election day, my bosses called upon two incredibly smart movement builders to meet us for a retreat in the woods and teach us the tools that kept them sane and focused.

Beth Zemsky came and taught us about the Intercultural Development Continuum and how our developmental mindsets can fuck with our perceptions of similarities and differences, fear or curiosity, certainty or openness. And Debra Peevey came and taught us about the Enneagram.

At this point, that was FIFTEEN YEARS AGO! I remember so many moments from those first conversations about the Enneagram like they were yesterday.

On a piece of flipchart paper, Deb drew out the symbol of the Enneagram, introduced us to the head, heart, and body/gut triads, and began to paint a picture of how nine different orientations to life can lead to wildly different reactions to the exact same experience. It both blew my mind, and also felt exactly right as she was explaining all nine orientations to life and living.

Please remember, we were so tired and so crabby. No amount of walking in the woods and eating family meals lifted the malaise and exasperation of the cloud layer over us, screaming, “What in the hell are we supposed to do next?!?!?!?!”

Deb was gentle. Deb was a pastor by trade (although she’s not religious now). Deb had done stints as a hospital Chaplain and came out and of age at a time when staying closeted was truly the only way to keep your job, your home, and, at times, even your life.

What I recall about that retreat and those handful of days learning this new framework together was that I had much more than one ah-ha.

My work team and I were a movement family by this point. We spent well more than 12 hours per day together and even moved and lived in the same community housing from time to time. We were called to do this work, and we had front-row seats to one another’s flaws and shortcomings on the daily.

By spring of 2009, I was pretty judgmental (more in my head than out of mouth, thank God, but it still wasn’t a good look). I would think (and at the time – believe) things like,

 “She can’t do that, she’s so rigid!”

 “He’s always so sullen and resistant!”

 “They just refuse to be reliable!”

And because I had just spent 24 months in a row talking to tens of thousands of voters, I would out loud self-identify in the following way, “I have my heart nearby in case I need it. Picture it in a tiny backpack. I can take it out and plug it into my chest if and when that becomes necessary.”

The older, wiser Trina can now have so much compassion for that phase of my discovery. My feelings were deeply hurt; I could not take steps forward and talk to more people if I felt like one big raw nerve. At that time, to survive, I compartmentalized.

Lucky for me, my friends, and my clients, I now live life with my heart plugged in. I am not afraid to feel. I now know my feelings are not going to kill me. I’m more like a 1980s Care Bear, ready and willing to do that Care Bear Stare out from the middle portion of my body whenever it is needed.

I have now been a student of the Enneagram for fifteen years. My study got even more focused when Alfonso and I started Team Dynamics back in 2017. We worked with Deb monthly to understand how our different Enneagram types would influence our work, decision-making, and general co-founder relationship.

I am an Enneagram Type 8 – for those of you wondering ;)

Before you make a ton of assumptions about what that means, know that Donald J. Trump and Martin Luther King Jr. are also 8s. It’s a wild club.

Like all types, I can choose to use my skills, superpowers, and special insight as an 8 for good or evil. It’s up to me. The same is true for you. My Enneagram type is NOT a premonition or foregone conclusion about how my life will go. It is a mirror that can invite deepened self-awareness and self-discovery if I am interested in pursuing it.

This coming week, I have the privilege of learning from my teacher’s teachers. When Deb retired her practice upon turning 70, she referred many of her students to her teachers. So now, I have a new Enneagram coach that I meet with twice per month, and this will be my second retreat in a three-part series which I’m attending alongside my dear friend Jeffrey.

Last year, he and I did our first Enneagram retreat together virtually. That meant we got to stay in our own homes and had the benefit of learning from folks from more than 10 different countries and contexts. This year, we decided to try out the in-person offering to learn how that feels for us. I will be flying in from Minneapolis, Jeff will be arriving from Seattle, and we’ll get to hunker down at a retreat center outside of San Francisco for nearly a week with what my current coach calls, “other friends on the path.”

As I said, Enneagram is not the only thing I study. I am also a student of the Intercultural Development Continuum. I am a student of minimalism. I am a student of movement building. I am a student of communications and political persuasion. I am a student of comedy, writing, art, and LGBTQ history. I find U.S. history fascinating and confusing. I try when I can to learn about psychology, and anthropology, world religions, and the future of tech.

I share this because I caution folks who treat any singular tool or worldview as “the one.” I feel perfectly comfortable weaving all of these learnings together because they are different ways to deal with the philosophical and tangible conundrums of being a human.

For me, the revelatory nature of the Enneagram in my life can be summed up like this:

- My goal is to continue to become a healthier version of myself (not a different person altogether).

- It makes all the sense in the world that my reactions are what they are given who I am and my life thus far. However, rather than be governed by my reactions, I can consciously choose my responses.

- I can thank my Ego for protecting me in my younger years when I struggled to understand what this human experience was all about; now that I’m fully an adult grown up, I can tell my Ego to go take a seat and let it know in no uncertain terms “I’ve got this. I’m gonna take it from here.” ;)

- Because I study the Enneagram and spend time with my teachers, I am now actually empathetic (not performing fake or shallow empathy). I can now recognize, at a deep level, when shit goes sideways and people are in the midst of acting out, it must be coming from somewhere. People are very afraid, very angry, very ashamed, or a combination of all three

– and being swept up in those feelings is always a beast.

- As an 8, I have shifted my previously distorted thinking about strengths and weaknesses. I now know that my innocence is my essence, and it’s where my magical creativity and clarity come from—a fresh perspective, a new possibility, a clean slate, and a gentleness that can guide me and us home. (War, cruelty, and deep dehumanization cannot happen when we are busy being gentle.)

If you are interested in learning more about the Enneagram from teachers I trust, I highly recommend both the Riso-Hudson school of thinking and teaching through The Enneagram Institute, and the Chestnut-Paes Enneagram Academy which you can find at https://cpenneagram.com.

I am guessing that you have found value in various tools and perspectives that have helped you up your game regarding your inner work. There are incredible racial and gender justice practitioners in my life and in my orbit who share that they experience value in:

 12 Step programs

 Insights (colors)

 Myers-Brigs (MBTI)

 Family systems theory

 Astrology

and more.

As I share about my appreciation for the Enneagram, I strongly encourage you to AVOID thinking of yourself as only “loyal” to one way of pursuing your growth. Many of these self-inquiry tools, when taken seriously and not used as an excuse or a weapon, can unlock incredible self-discovery that can lead to strategies, tools, and deepened understanding for living a more aligned and fulfilling life.

No matter which school of thought turns you on and makes sense to your brain, the question I like to ask is, “now that you are aware that ________ is a pattern of your thinking and behavior, what are you going to start trying?”

For real, rather than just knowing something, what are you planning to DO about it?

How do you want to grow and expand? How do you want to move away from judgment and towards curiosity? How can you begin to chart a path from “I cannot” towards, “I could try this and see how it feels and goes differently?”

As you know, anti-racism is an ACTION stance. It is an open-heart posture that feels compelled to do something about Centuries of dehumanization through the creation of the project of racism. Valuing women, genderqueer folks, and femme-identifying people means ACTIVELY ENGAGING in the inner and outer struggle Americans are having about what the fuck they are so afraid of if the patriarchy finally crumbles?

These are not light lifts. In my experience, they are heavy as hell. And heavy work requires both strength and endurance.

So, for this next week, I’m going to unplug and sit in a circle with people from around the world who are in the process of learning, growing, deepening, and trying hella hard.

I’ve got this quote hanging up in my office:

“I want to be around people that DO things.

I don’t want to be around people anymore

that judge or talk about what people do.

I want to be around people that dream and

support and do things.”

- Amy Poehler

Same! Good call, Amy ;)

Therefore, I’m headed out for the week. I’ll check in again once I’m back.

In the meantime, feel free to email me (trina@trinaolson.com) about the tools and frameworks you find valuable in your life and practice. I’d love to hear what speaks to you!

More next week,