Why (and how) do you meditate?
A gentle introduction for the curious and the quietly skeptical
The question has come up many times over the years: Why do you meditate?
Friends have asked, colleagues have been curious, and occasionally it slips into conversation like a pebble tossed into a still pond, or sometimes more like a floaty in a swimming pool: a little awkward and waiting to be noticed. I’ve never quite nailed the answer. Not because I don’t know, but because it’s hard to say out loud what’s easier to feel in silence.
Most recently, the question resurfaced while I was on a camping trip with my brother. We were sitting in our tent, days before I left for my first five-day vipassanā retreat. He asked me with genuine curiosity: Why do you do it? I stumbled through a few thoughts, then pivoted and introduced him to the Waking Up app by
, half-joking that Harris could explain it far better than I ever could.Still, something about that moment stayed with me.
It wasn’t a new question, but the timing made it feel like one. I was heading off into silence, about to immerse myself in a practice I’d been slowly building for years, and I couldn’t quite articulate why. There was a flicker of embarrassment. Shouldn’t I know by now?
But that’s the tricky thing about meditation. About most meaningful things, really. They often resist tidy explanations. As I’ve been writing more about my vipassanā experience, I keep running into the same conundrum: words are useful, but also deeply limited. There’s a Zen proverb I love: “The finger that points at the moon is not the moon.” Language can gesture toward something real, even beautiful, but it will never be the thing itself.
So this piece is my attempt to point. To share, as best I can, why I meditate, what it’s taught me so far, and how I weave it into daily life.
If you’ve ever been curious about meditation, or unsure if it’s for you, maybe something here will resonate. This is the first in a series of “Why (and how)” reflections. I don’t presume to know the “answers.” But I do have a path. And sometimes, sharing the path is as good a starting point as any.
Who is this piece for?
This piece is for anyone who’s ever been curious about meditation. Maybe you’ve tried it a few times. Maybe it felt good. Maybe it didn’t. Maybe you’ve wondered if there’s more to it than relaxation or breathing exercises.
What’s the point? Why bother? Is it just about feeling calm, or is there something deeper?
I don’t know if I can thoroughly answer those questions. This is simply one perspective (my perspective) on why I meditate, and why I think it’s worth spending some time with.
If you’re already a long-time practitioner, you may find pieces of this that resonate. If so, I’d love to hear what keeps you coming back to the cushion. But this piece is mostly an introduction, an attempt to put into words what often resists my attempts to explain.
What does meditation mean to me?
To me, meditation isn’t about becoming calmer, more focused, or even more compassionate. All of those are wonderful side effects of the practice. They’re real, and for many people, they’re reason enough to begin. But they’re not why I keep coming back to it.
The clearest expression I’ve heard came from Joseph Goldstein, when he shared a lesson from his teacher, Anagarika Munindra. Munindra had once told him, “If you want to understand your mind, sit down and observe it.”
That was the moment it clicked for me. It seemed so obvious, yet I had never quite framed it that way. If you want to understand something better, you pay attention to it. Not once, but over time. Not selectively, but steadily. And that’s what meditation is for me: an ongoing practice of paying attention. Paying attention to the mind, to experience, to the subtle currents of thought and feeling that usually pass unnoticed.
Meditation creates space. It allows for awareness. Not “awareness” in the abstract, but in the moment. Awareness, to me, is a kind of clear seeing. It is the capacity to observe without clinging, without judging, without turning away. To be the watcher without needing to be the doer. To notice a thought without becoming it. To see a reaction rising, and not immediately follow it. That space can be quiet, but it can also be challenging. Still, it is the space where insight becomes possible.
There’s another explanation I love, this one from Pema Chödrön. She writes that we don’t sleep to become better sleepers. We sleep so that we can be more awake when we aren’t sleeping. Likewise, we don’t meditate to become better meditators. We meditate to become more aware, more present to our lives, more intimate with the moment we’re actually in.
I see meditation as a way of learning to live with more clarity. It offers a glimpse beneath the habits and assumptions that usually run the show. Over time, it has helped me begin to relate to this ever-shifting idea of “self” with a little more openness and a little less grasping. It hasn’t erased my patterns, rather it has made them visible. And seeing clearly, even briefly, is the first step to changing how we live.
What led me to meditation?
I first experimented with meditation over 30 years ago, sometime in my adolescence. But calling it a practice would be generous. I tried sitting still, “clearing the mind,” focusing on the breath. Okay, time’s up. It felt a little futile.
Many years later, I gave it another shot. This time through popular apps like Calm and Headspace. While I can see how these apps help many people, they never quite landed for me. I wanted something deeper, something that explained why I was doing what I was doing.
That’s when I stumbled upon Sam Harris’s Waking Up app. It combines guided practices with thoughtful conversations and theory. It didn’t just offer calm: it challenged how I thought about meditation itself. And for the first time, it felt like a path worth walking.
Why I started, and why I keep returning
I used the Waking Up app for years and loved the breadth it offered. It is filled with guided practices, deep philosophical conversations, and frameworks that helped me understand what meditation was and why it mattered. It helped me build a habit. It gave shape to something that had always felt just out of reach. I still recommend it often. But these days, I find myself using it less.
Earlier this year, I attended my first vipassanā retreat. It was five days of silence, reflection, and deeply focused meditation. Vipassanā is a specific form of “insight” meditation rooted in ancient Theravāda traditions. The practice itself is deceptively simple: focus your attention on a single anchor, often the breath. Notice when the mind wanders. Return to the anchor. Repeat. Over and over.
But underneath that simplicity is a profound invitation: to see the mind clearly. To observe reality as it is, not as we think it should be. To come into deeper contact with the self. Not the usual curated identity “self” that we often present, but the moment-to-moment stream of experience we usually overlook.
My experience on that retreat was so meaningful that I’m now attempting to write a book about it (more on that soon). Since then, my practice has shifted. I still return to the guided sessions on Waking Up from time to time, but what draws me most now is silence. Sitting quietly, returning to the breath, noticing what arises. There is something about the unstructured stillness that allows insight to emerge unprompted, unpolished, and unexpectedly honest.
The best way I can describe it is this analogy:
Imagine sitting in a crowded auditorium just before a live performance. The room is buzzing with conversation. Voices overlap, laughter echoes, snippets of story pass by without any context. It’s so loud that the only thing you can really make out is the person next to you. That’s how my mind often feels: layers of thought, emotion, and memory all jostling for attention. And usually, the loudest voice wins.
But then, the lights dim. The curtains begin to close. A hush falls over the room. And suddenly, from the back of the auditorium, you hear something quiet and clear. It’s a conversation so compelling, so true, that you find yourself straining to catch every word. You hadn’t noticed it before. It had been there all along, drowned out by the noise.
That’s what meditation gives me: enough silence to hear what was always there. It lets me see thoughts as thoughts, not as facts. It helps me loosen the grip of identity, of habit, of being swept along unconsciously. And in that space, in that contrast, something deeper begins to speak.
How I practice
I’d love to say I meditate every day. I try, but some days slip by, especially with three young kids in the house. Like most things that matter, it’s a rhythm I aim for, not a rule I always meet.
The best time for me is early morning, before the day begins. When the house is quiet, and I can claim just a few moments to myself, the practice feels like a small act of grounding before the current of daily life picks up. It’s not always long. Some days it’s ten minutes. Other days, maybe twenty or thirty. But even a short sit can reset how I relate to the rest of the day.
When I practiced with guided meditations on the Waking Up app, my sessions were usually around fifteen minutes. It helped to have a voice to follow, a structure, and a bell to signal the end. Now that I’ve shifted more into silent breath meditation, I usually set a timer. It frees me from that nagging question: Has it been long enough? It lets me settle more fully into the sit.
But some mornings, if I wake up early enough, I don’t set a timer at all. I just sit. No countdown. No endpoint. Whether it’s ten minutes or an hour, I let the session unfold. Those are often the most powerful ones. When I’m not watching the clock, I can simply be. And that, at its core, is what the practice is about: being present without needing it to be anything more than what it is.
My practice isn’t limited to a cushion. One of my favorite forms of meditation is hiking in the hills near my home. Sometimes I find a bench or a rock and sit quietly, but more often, the walking itself becomes the practice. A steady breath. A single step. A moment of awe. I’ve yet to master it, but my Golden Retriever, who joins me on most hikes, seems to have reached the arahant stage of enlightenment. No striving, no distraction. Just a full-hearted presence.
I also find something similar in writing. There’s a kind of stillness that arrives when I’m deep in the flow of a sentence, sensing my way through a thought. Natalie Goldberg, in her book Writing Down the Bones, writes about how writing became her Zen practice. That idea has stayed with me. Like hiking, or sitting, writing can become a way of listening. A way of being in direct contact with experience as it unfolds.
What I’ve learned (so far)
People sometimes ask if I can completely clear my mind during meditation. The honest answer? Only for a few moments at a time. Maybe a few seconds if I’m lucky, occasionally almost a minute. However, I’m not sure if that’s entirely the point.
I used to think the goal was silence, total stillness, a mind free of thought. But over time, I’ve learned it’s not about eliminating thoughts. It’s about noticing them sooner. It’s about shortening the time between being lost in thought and recognizing that you were lost. That’s the shift: from being swept away to gently returning. Again and again.
How quickly can you notice the next thought? Can you catch it as it arrives, before it pulls you in? Can you observe it without judgment, without clinging, and then let it dissolve just as easily?
Doing this over and over trains the mind to rest in awareness, not in the stories it tells. And in that process, the mind begins to quiet. It quiets not because you’ve forced it to, but because you’re no longer fueling the noise.
That kind of quiet is unlike anything I’ve found anywhere else. Not even sleep brings that level of rest. It’s not always easy to get to. But when it comes, even for a moment, it’s unmistakable.
And in those moments, something deeper starts to reveal itself. Something about the nature of the mind. About what we call the self. About how easily we believe we are our thoughts, until we realize we’re the one watching them.
As for where that journey leads, I won’t give too much of it away. But if that stirs even a little curiosity, I’d suggest trying it for yourself.
Where to begin if you’re curious
If any of this has sparked your curiosity, I recommend starting with the Waking Up app. Sam Harris has curated a thoughtful blend of teachers, traditions, and practices, and his “Introductory Course” is a great entry point for guided meditation.
If that particular style doesn’t resonate, there are many other apps worth exploring. The key is simply to begin: to try, to sit, to notice.
And if you ever feel called to go deeper, I highly recommend exploring a vipassanā retreat. It’s an intense experience to be sure, but a profound one. That said, it helps to know how to swim before diving into the deep end. A little practice beforehand can go a long way.
Resources for deeper exploration
If you're interested in exploring meditation further, here are a few resources that I’ve found especially helpful:
Waking Up App – A well designed app by
, blending guided meditations with in-depth conversations and theoretical insights. A great place to start or deepen your practice.Spirit Rock Meditation Center – Located in Northern California, this center offers retreats rooted in vipassanā and loving-kindness practices.
Insight Meditation Society (IMS) – Based in Massachusetts, IMS offers silent retreats and meditation courses grounded in the Theravāda tradition.
The Untethered Soul by Michael A. Singer – Not a meditation manual, but a powerful companion for understanding awareness and inner stillness.
Writing Down the Bones by Natalie Goldberg – A Zen-inspired invitation into writing as meditation. For those who love language and stillness, this book bridges both worlds.
A Field Guide to Nature Meditation by Mark Coleman – A guide to bringing your meditation practice outdoors, with reflections and exercises to help you reconnect with the natural world.
10% Happier Podcast with
– A practical and down-to-earth resource for learning about meditation through conversations with teachers, scientists, and skeptics alike.Any Book Written by Pema Chödrön – Her words are a steady, compassionate guide for navigating uncertainty, fear, and the desire to be more fully present.
Be Here Now Network – A treasure trove of talks and teachings from luminaries like Ram Dass, Alan Watts, Joseph Goldstein, and many others. A beautiful resource for deepening the inquiry.
Of course, there are countless other books, teachers, and centers doing beautiful work. If you have any favorite resources or retreat experiences, I’d love to hear about them in the comments.
What a generous resource for folks who are curious!
Love the auditorium analogy! It’s spot on. The goal isn’t necessarily silence, but noticing what’s there when things quiet down.
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