The Enneagram’s true purpose

I’ve taken the Myers Briggs, the DISC, the Kolbe, a proprietary test that my executive coach administered, and probably a couple other assessments along the way that I’m forgetting. Usually they come up in the context of business, with utility like constructing a complementary team, or understanding your coworkers, but in all of them I always end up in the same spot: “Interesting. Now I guess I’ll go back to living my life.”

The Enneagram has been much more useful.

The original thoughts behind the Enneagram are either from ancient Egypt, or 4th century Alexandria, predating all the other assessments by quite a bit. Nothing lasts that long without having something of import to it (if the DISC is around in the year 4,500, we can revisit this).

Nevertheless, when I originally heard about it I lumped it into the same category as the other assessments, another way to categorize people that is neither more or less accurate than any other. And in a sense, honestly, it is exactly that. But where it differs, and becomes much more than a simple bucketing exercise, is in how it’s intended to be used.

From the Enneagam Institute:

One of the most profound ways of understanding the Levels is as a measure of our capacity to be present. The more we move down the Levels, the more identified we are with our ego and its increasingly negative and restrictive patterns. Our personality becomes more defensive, reactive, and automatic.

The movement up the levels is simultaneous with being more present and awake in our minds, hearts and bodies. As we become more present we see our personality objectively in action rather than “falling asleep” to our automatic personality patterns. There is therefore the possibility of “not doing” our personality.

I’ve found that the best leaders, and myself when I’m at my best, are those people who are fully invested in the person they’re leading. The more present the person, the better the leader. For that, but not only that, reason, I’ve spent considerable time and effort rewiring my brain to focus on being ever more conscious in and to the moment.

Beyond leadership, this is also my understanding of the Path that is in some way referred to by nearly all the wisdom traditions (Buddhism, Hinduism, Advaita Vedanta, Christian Mysticism, Kabbalah, Taoism etc), as well as plenty of secular thinkers (Sam Harris, Brene Brown, etc). Even Lululemon bags note that “living in the moment may be the meaning of life,” although that probably only proves I’m subject to marketing.

Either way, as a longtime “intellectually superior atheist” this wasn’t the path I’d expected to go down. If the me of today were to meet the me of any age between 17-33, I’m sure I would have laughed at myself. Or

But then again, viewing that conversation through the handy lens of the Enneagram, that would have been a level-6 laughing up at a level-2, from deep in the clutches of his automatic and defensive personality patterns.

I’m good with that. The 17-33 year old me wasn’t near as effective a leader.

Czeslaw Milosz, on Love

For this Valentine’s day, I’m reminded that the prerequisite to loving someone is loving yourself. Like an airplane mask, you can’t care for someone else if you haven’t cared for yourself first.

Love means to learn to look at yourself
The way one looks at distant things
For you are only one thing among many.
And whoever sees that way heals his heart,
Without knowing it, from various ills.
A bird and a tree say to him: Friend.

Then he wants to use himself and things
So that they stand in the glow of ripeness.
It doesn’t matter whether he knows what he serves:
Who serves best doesn’t always understand.

~ Czeslaw Milosz, New & Collected Poems 1931-2001

In college I often found myself looking for hidden meanings in poetry, but these days I find myself surprised at how literally things like this seem to be meant.

My favorite hot spot I thought I’d never go to: The Hermitage

I’ve gone on retreat a number of times now, so far all domestic although I hope to visit Tibet or Nepal soon (and a hike of Machu Picchu coming up may almost count, depending on how meditative my hiking becomes), but for the longest time I’d thought that retreats were much less accessible than they actually are.

I thought that in order to go on a contemplative retreat you’d have to travel to Colorado for a week with a guide, and the whole thing seemed like such a big to-do that it was never the right time. Fitting a week of “doing nothing” into a busy startup founder schedule is unrealistic, I thought. And because of that, I didn’t experience the true depth of reflection and force of insight that are possible through retreat until early 2019, when a friend of mine introduced me to The Hermitage.

The Hermitage is a Christian-flavored retreat space in Three Rivers, Michigan. I am not a Christian, so when I first checked out the website I was a bit nervous that I would not be welcome, but my friend reassured me that it was a space that was welcoming to all, as long as you were looking to go inward. Besides, I am also not a vampire, so a couple crucifixes aren’t going to hurt me. The part of the experience that initially appealed to me, in addition to the inaccessible mystique that a “retreat” had developed in my head, was that The Hermitage was purpose built for short retreats, as short as a single day. I’m sure they do longer ones as well, but the opportunity to retreat for a whole day with only a single hour drive each way got me over the hump. I was finally able to justify the investment, and in hindsight it was ignorant to wait as long as I did. The opportunity cost of not doing the introspection was larger than I had thought.

It’s way out in the country, sufficiently away from everything such that even the travel there starts to put your mind in a different, more relaxed, posture. Theres a multi-purpose sign at the driveway that says “slow down.” The campus itself consists of two large buildings, one a sort of multi-functional gathering area complete with a chapel (which I couldn’t bring myself to spend time in initially) and a sitting room/library (which of course I loved), and the other a lodging with a kitchen in which they serve regular meals (although I’ve endeavored to fast each time I’ve gone) and a bunch of rooms for retreaters. You can rent the rooms out for the day, as I’ve done, or I’ve seen people staying there for the weekend or the week.

In addition to the two larger buildings, the real beauty of the Hermitage is the campus. A few acres of wooded trails extend from the main residences, interspersed with natural and cultivated landmarks like a lean-to at the top of a steep cliff overlooking a river, and an ankle-high spiral maze within which you can practice walking meditation. It’s beautiful everywhere you look, but in totally distinct ways. It’s breathtaking both in its scale and its complexity.

My favorite part of the campus is the cabins. Four, single-room buildings dot the deep woods, with names like “Thoreau,” “The Hut,” and similar. Each of these is slightly larger than the bed contained within, and also includes some sort of desk area, for reading/writing. The bathrooms are outhouses, which may be a turnoff for some but since I try to fast while there have only served as scenery adding to the comprehensive different-ness of the place. My habit now is to rent out one of these cabins for the day, and then split my time between sitting meditation within the cabin, walking meditation around the grounds, and a bit of journaling inside the lean-to (because of the view).

Since I was introduced to this space, I’ve brought a few friends with me as well; I’ve found that running a business tends to demand so much of a person that retreats can be quite appealing, although like me most think of them as something monk’s or artists do. Going deep internally with friends–we always end the day in the sitting room to discuss our experience–has added to the depth of some of my closest friendships.

There are no “rules” for retreat, per se, but people there generally try to observe silence. This is amazing, and not as difficult as people think it will be (the hardest part for someone as social as me is not saying hi if you happen to pass someone on a trail). But that’s not a rule, and you won’t be kicked out if you do talk. In an effort to get the most out of my time, I also make it a point to, and I can’t stress this enough, leave my cell phone in the car. To make this work I always let people know I’ll be inaccessible for 8 hours, and surprise surprise, the world doesn’t end while I’m away.

If you have interest in contemplative retreat, and you have not yet gone on one, I highly recommend finding a local spot like The Hermitage. A day is plenty of time, and can be a great introduction into the benefits of taking time to dig internally. It’ll take more than that one time to go beyond all the roles you play and find out who you truly are underneath all those mental constructs, but that process is a lot like the old adage about eating an elephant (as are so many things worth doing). And if you are in Michigan and would like to try out the Hermitage with me, I’d be happy to “host.”