Jay Michaelson is surely a contender for the most interesting and accomplished person alive. His areas of expertise are so wide-ranging that one wonders how they can occur in a single human being.

He is an attorney who also has a PhD in religion. His areas of expertise include Judaism, Buddhism, law, politics, meditation, and mysticism. He has been a professional LGBT activist, a university assistant professor, a nondenominational rabbi, a clerk to a judge of the U.S. Circuit Court of Appeals, a software company founder, a writer and speaker, and (this is how I first got to know him) a meditation teacher. Over the years, he has written many books and articles and appeared in numerous media. He has spent countless hours not just studying spiritual topics, but actively seeking mystical experiences.

Expanding the Mind Into Frightening Directions

Michaelson is my favorite teacher on the Ten Percent Happier meditation app. However, I also find him the most emotionally demanding teacher on the app. He expands my mind into new directions; but those new directions are difficult for me.

For example, one of his best guided meditations (IMHO) is an invitation to the meditator to sit with anxiety and fear. I don’t know about you, but I spend most of my time trying to run away from anxiety and fear. Naturally, this only gives these emotions more power over me. To sit with them, for longer and longer periods, is to train yourself to be able to tolerate them. But it’s difficult—like learning to be less afraid of heights by scaling to higher and higher summits and peering over the edge.

So, even though Jay Michaelson is my favorite teacher on the app, I often avoid listening to him, because I’m emotionally tired. Like, all the time. But I aspire to listen to his guided meditations more often, and also to some of the other hard-hitting meditations on the app by other teachers.

(I complained to my psychotherapist about this. He said, don’t be too hard on yourself. So maybe I’m not as lazy as I feel. Or maybe I am. Where is the balance between pushing yourself to do more, and giving yourself a break?)

Edging Toward Enlightenment

Michaelson’s 2019 book Enlightenment by Trial and Error fascinates me for two reasons.

One—it contains an obscene amount of wisdom. Just out of control sagacity. It is unusual to discover someone who has done months-long meditation retreats and experienced mystical states firsthand; and who also has a doctoral degree for which he studied two major world religions. It’s a winning combination of experience and scholarship—which, incidentally, it seems to me, is uncannily mirrored in two of his other areas of expertise, his LGBT activism (experience) and law degree (scholarship).

All of this is to say, when reading this book, I starred and marked it all up. There is wisdom all over the place here. The wisdom is not doled out stingily. Now—the sagacity is, admittedly, haphazard; but its prodigality more than makes up for the messiness of it all.

Another source of messy, prodigal sagacity? The extras you’ll get as an L.A. Patron! I can’t promise enlightenment, but, hey, no one’s perfect. . . .

Two—the book is fascinating because it is a collection of essays that Michaelson wrote over a ten-year period. The reader, thus, can track the progression of his thinking. Truly, he progresses toward greater and greater wisdom.

I admit, some of the earlier essays did not captivate me as much as some of the later essays. But, as Michaelson himself explains in his introduction, the earlier essays have value precisely in their weaknesses. It was instructive to watch him learn and grow.

For the most part, this was a process of watching him let go. In the earlier essays, he expresses a great love of and attachment to the traditions of Judaism and Buddhism. As the essays progress, he lets go of more and more attachments, until, by the end, he has distilled out everything extraneous and gotten to the essence of both religions.

Spoiler alert: the essence turns out to be the same! (My previous blog post explores this idea of the essential sameness of all attempts at spirituality.)

When Life Pops Like Popcorn

Following is one of my favorite passages from the book. Michaelson writes, in the essay “Rethinking Spirituality,” about the various sublime mystical states he has experienced.

Wow—mystical states! Tell me more!

As a meditator, I know that so much of meditation is drudgery. Or so it feels to me, a nonexpert. So when Michaelson writes about mystical states, I’m all ears. Will I ever experience something like that?

He attempts descriptions of some of these mystical states. And he writes about some of the profound insights he gained. And then he writes this:

“In fact, [mystical] states lead to insights of all kinds. . . . Jay’s messy life popped like popcorn.”

As with the moon metaphor, again he’s come up with some remarkably vivid symbolism. But while I loved the imagery of this passage, what I loved even more was the realization that—drumroll—this has happened to me!

It’s common for inexperienced meditators to get caught up in trying to focus on the breath, trying not to think, trying to be calm, etc. When I meditate, I have noticed, I often end up doing the opposite—ignoring my breath, running wild with the thinking, and inhabiting a mental state that no one would call “calm.”

But! I have noticed that vitally important thoughts often pop up in just those moments when I am “supposed” to be focusing calmly on my breath. These thoughts are just as spontaneous and surprising as popcorn popping! It’s like, I’ll spend every waking moment of every day ruminating about stuff that just doesn’t matter, but when I sit down to meditate, the stuff that matters pops into consciousness.

Suddenly, unsolved life mysteries have clear answers, complete with action items. Suddenly, vague, unsettling emotions crystallize into concrete problems that can be proactively thought about.

This reminds me of experiences I have had with dreams. I wonder whether, when I meditate, I’m tapping into my unconscious in a deeply significant way.

You, Too, Can Be a Mystic

This gives me hope that I, too, mortal that I am, can access something approaching spiritual wisdom. It gives me hope that, indeed, I already have.

Gosh, writing this, I feel inspired to do a better job of meditating (more often, and not at times or places when I’m likely to fall asleep). I also feel inspired to reread Michaelson’s book (though I’m not much of a rereader, honestly; so we’ll see on that one).

Have you experienced mystical states?