I’m always talking about how the Enneagram is an incredible tool for self-awareness. 

But after watching some of the video testimonials from my Enneagram retreat last weekend, what really struck me was how much people loved learning about other people.  

(You can watch them too — I put them up on the description page for my upcoming Enneagram retreat. Just click this button.)

What people said reminded me of how learning the Enneagram caused a radical shift in the way I relate to others.

As an example, when I took my first Enneagram class, I had a larger-than-life boss that I loved (and still love—he’s a good friend, and probably reading this email). He had the biggest laugh in the room, and he had an incredibly powerful presence that charged his social environment with a primal, fun, almost rebellious energy. He made you feel fully alive, but he could also get into a towering rage, be confrontational, and try to “make” you see things his way.

After learning the Enneagram, I realized that my boss was a type 8.

It turns out that type 8s often come to occupy positions of authority because of their self-confidence and natural ability to lead. But employees of 8s can sometimes feel intimidated when their boss’ assertiveness manifests as a bulldozing forcefulness.

Studying the Enneagram helped me to see that, as an 8, my boss was using anger to make himself feel alive and to defend against a feeling of inner deadening. This was a major aha moment for me, and it unlocked a lot of compassion for him. Sometimes knowing the nature of someone else’s suffering is all it takes to love them at a whole new level. 

I remember the conversations that I had with him after that — they were very different.

It was eye opening for me, as a 3, to realize that 8s respect others when they stand their ground. That gave me the courage to debate him and not cave in or get defensive when he raised his voice. Over time, I became more solid and unperturbed in the face of his forcefulness, and I even challenged him to notice when he was pushing too hard. Most importantly, I began to see through his gruff bravado to his huge, generous heart. I loved him for it, and I absolutely know that he felt that from me, and still does.

The beautiful consequence of this was that once he came to see that I wasn’t a push over, he got more comfortable around me and began to reveal more of his tender side. 

Once, when I was describing the Enneagram to him, I told him about how, as a 3, my deepest fear is that I’m worthless.

I’ll never forget what happened next.

He stopped me mid-sentence by putting his hand on my shoulder and looking me hard in the eye. A tear welled up in his, and he said, “Son, you ever feel like you’re worthless… you call me. You haven’t done worse things than me, and I’m not worthless.”

It was a sledgehammer of love. It almost knocked me backwards. As I type the words, I can still feel their power.

This is just one of many examples of how the Enneagram helped me deepen my relationships to a level of love that I didn’t know was possible before. 

It is in large part because of the Enneagram that I have come to trust my own strength to be in the presence of forceful people without getting swept away by their tide, and the Enneagram continues to help me remember my truest, strongest, most loving self.

Rediscovering the Enneagram through the eyes of my workshop participants, I am seeing how the Enneagram is a set of training wheels for seeing your own and others’ goodness — and indeed, for seeing that all people, even the most frustrating ones, have goodness on the inside.

And once you see that clearly, you can live in a way that calls forward the goodness in other people, which is, in my opinion, the greatest gift of all.

Love,

Josh

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