I Don't Know Which Season This Is

I have been asking myself a question I cannot answer.

The question is this: is this a season of liberation, or is this the thing that looks like liberation?

I ask because I am, by temperament and history, a person who can swing. Not widely — I'm not dramatic about it in public — but enough that the people I trust have learned to notice. I go from spiritual as hell to forget it, I'm just going to make money. From rigid rule-following to something that looks a lot like not caring about the rules at all.

I'm a one on the Enneagram. The black-and-white ones. We can go a long time performing goodness before something in us snaps. And when it snaps, it doesn't look like collapse. It looks like freedom.

That's the thing I can't get past.

A few years ago I was rigidly careful about certain things. Rules I had internalized so thoroughly I didn't think of them as rules — they were just who I was. Careful. Measured. Responsible. A person who did not take shortcuts with things that mattered.

At some point the careful thing started feeling like a cage I had built for myself and then forgotten I built. And I started to feel something that I would describe — from the inside — as coming alive. A new chapter. I'm living a new life now. The old constraints didn't apply because the old me didn't apply.

I told myself this was health.

I still think some of it was.

But here's what I've been holding: the people I trust did not experience it the same way. They did not see a man becoming more free. They saw something else.

I am not going to detail what they saw, because that is their story to tell. But they were right about more than I wanted to admit. And I was wrong about what I thought was freedom.

That's the part a one on the Enneagram doesn't like to sit with. We are good at being right about things. We are less good at being wrong about ourselves. And when we finally loosen up, when we finally let go of the cage, we can mistake the loosening for arriving — when actually it's the beginning of a longer, slower, harder process of actually becoming who we are.

I've read enough to know the signs. I've lived enough to know they can look exactly like the signs of the other thing.

There is a version of loosening up that is health. There is a version that is a manic episode dressed in the language of liberation. They feel identical from the inside. The difference is what you leave in your wake.

I have a psychiatrist appointment next week. That is not a dramatic statement — it is a practical one. I am going because I want to ask someone who has seen this before to help me tell the difference. I am going because I love the people who were in the car with me, and they deserve someone who knows the difference.

I am speaking at a Chamber event this week about my work. I am building ventures, writing books, trying to make something that matters out of this particular corner of the world. I am — genuinely — more alive and more purposeful than I have been in years. I believe the work is good. I believe the season is real.

And I am also sitting with the fact that those two things can both be true. Alive and mistaken. Purposeful and running too fast. Building something real and also needing someone to look at you without the build and ask: how are you, actually?

That is the essay. I don't have a landing. I have a Tuesday appointment.

If you've been in this territory — if you've had to ask yourself which season it was, with some real stakes attached to the answer — I'd like to hear from you. Not because I have the next right move figured out. Because I'm not sure anyone figures it out alone.

Previously published in my own head, approximately 6am on the morning I finally decided to say something about it.