ten years of trying to meditate

the long road to a daily practice

Hey everyone,

I am nervous to share this email because:

1. It feels extremely personal.

2. I’m a novice; I don’t know much.

3. Future Ammar might cringe reading this.

But there’s one thing I know for damn sure. I spent almost a decade plodding away at meditation alone, a weird side passion. And it was crushingly lonely. I couldn’t find anyone else I knew who openly cared about this stuff. So I didn’t talk about it.

My practice changed significantly as I began mentioning it to some friends. Turns out they had also been trekking these backroads. Some for much longer than I had. What a relief, I’m not alone. Every encounter with them gave me more clarity, direction, and faith.

And then … things took off in ways I can’t put into words (but I will try!). After almost 10 years of false starts, I’ve established a stable, daily meditation practice. It has transformed me in ways that I did not expect.

I’m sharing what I wish I had come across many years ago. Maybe this will strongly resonate with only one or two of you. And that would make all of this writing worth it.

This is part one. Today, I’ll tell the story of my first ten years with meditation. It went horribly. In future emails, I’ll share what made the habit stick and why.

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ten years of trying to meditate

I first tried meditating right after college. Why? There are many reasons that bring people to the foothills of meditation. To heal trauma, to unwind anxiety, to better handle stress, to tap into their creative urges, etc.

What brought me to these foothills was a bewildering experience.

It happened shortly after graduating from college, when I was a math teacher in Florida. I sat on Jacksonville Beach, watching the waves crash and recede, crash and recede, crash and recede.

At some point amidst the crashing-and-receding, my vision filled with white light. I tingled all over. My body pulsed with sensations of joy and gratitude. It was as if the separation between me and everything around me suddenly disappeared. I felt at home.

As soon as I tried holding onto these sensations, they went away.

I wanted to understand what the hell just happened. Apparently, these types of experiences are not rare. Artists and athletes enter flow states; near-death experiences slow down the clock of life; out-of-body moments appear in the middle of sleep; etc.

It’s just that most people don’t talk about them. They become odd blips to shrug off.

Almost a decade later, I came across Henry Shukman’s One Blade of Grass, which described a similar experience with uncanny precision.

But without having encountered that book yet, I searched my memories for anything that seemed to relate.

And I couldn’t find anything. Which was a huge bummer, because I couldn’t shake this experience from my heart. I had glimpsed an unforgettable vista. There was more to life, a resonant undercurrent, that I couldn’t unsee.

I spent a few years trying to distract myself. Booze, weed, travel, startups, East Village, Dolores Park, music, art, anything that I could throw myself into. And I had a really fun time doing it.

But that experience on the beach left me raw and exposed. Something inside me opened up. I began feeling things very deeply, like the volume on life had been unmuted.

Sedating myself started to hurt after a while. After the come-downs, I still had that rawness waiting for me. So I went back into my memories to find something that might show me another way.

I remembered that in high school biology class, one of my friends was quietly reading a slim blue novella titled Siddhartha while the teacher droned on about beak sizes and natural selection.

Maybe this book by Hermann Hesse held the key? I bought it and finished it in one day.

“They both listened silently to the water, which to them was not just water, but the voice of life, the voice of Being, the voice of perpetual Becoming.”

I read it, I re-read it, and I sobbed, I smiled, I sat quietly with the story. I should meditate, I thought. That’s what Siddhartha did. That’s what monks do in monasteries. They have the answers, they’ve seen so clearly what I glimpsed for but a moment, so if meditation is good enough for them, it’s good enough for me.

I googled “How to meditate”. I came across the following (endlessly profound) pithy instruction:

“Sit down and follow your breath. If your attention wanders, gently return to the breath.”

I tried this for a few weeks but couldn’t get past 5 minutes without wanting to rip my hair out. Yawn. Fidget. Discomfort. Itch. Thought. Fantasy. To-do list. Fear. Anger. Boredom. Weekend plans.

I’m doing it all wrong. I can’t do anything right.

Fuck this, I’m done, it’s not working, whatever “the point” of this is, I don’t get it. Garbage waste of time.

While my attempts to meditate didn’t quite work out, I became aware of the tiniest of fires within me. A sincere desire for self-inquiry. Who am I? What is this all for? Why am I so dissatisfied? Why don’t I feel at home in this world? What am I trying so hard to upkeep?

Over the next couple years, I tore through all sorts of texts relating to psychology, the mind, psychedelic experiences, and the purpose of religion. Some standouts:

• PD Ouspensky, In Search of the Miraculous

• Carl Jung, Modern Man in Search of a Soul

• Stan Grof, Holotropic Breathwork

• Ram Dass, Be Here Now

• Chogyam Trungpa, Cutting Through Spiritual Materialism

I experimented with different practices that I came across from the above texts. None involved sitting still on a cushion and meditating.

These experiments culminated in an unnerving experience on the DC Metro. I sat facing the direction that the train was moving in. I noticed myself, I noticed the train, and I noticed the tunnel that the train hurtled me through.

I cycled through these noticings. Just like on the beach a few years prior, for a moment I felt that there was no distinction between me, the train, the tunnel, and the space we were all moving through. Nothing to grip or hold on to.

Years later, I realized I had cobbled together a super bootleg version of an ancient form of meditation — vipassana. Its angle? To cultivate insight into the nature of self and reality. To see things as they really are.

Anyways, you can probably guess that I didn’t know what that was at the time. So I quietly freaked out. I felt completely out of control. What was this experience trying to show me?

Soon after, I stopped my experiments. I focused on my career. I got married. I moved to Brooklyn. I made a good life for myself.

It took me some years to get back into this meditation thing. I tried a bunch of prescribed methods (everything from Headspace to capital-B Buddhism), keeping a 20-minute practice for a month or so before I dropped it in disgust.

It just wasn’t sticking. I was too much at war with myself to do something so simple.

Maybe I should just relax, stop trying to do it right, and simply notice what happens, and then keep noticing.

…Could it be that straightforward? Why is that so hard to do? This insight changed everything.

This email has grown quite long, so I’ll stop here. More to share in future emails. If you’re giddy to know what worked, I’ll drop some links below for you to check out and explore for yourself.

• Reginald Ray’s Journey of Individuation

• Wulf & Lewthwaite’s OPTIMAL Model for Athletes and Their Learning Environments

• Michael Taft’s Nondual Awareness Meditation Series

• Domyo’s Shikantaza: Having the Guts to Just Sit and Let Go of Doing Anything

• Omori Sogen’s Introduction to Zen Training: A Physical Approach

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Ammar