I often begin the meditation groups I facilitate by explaining that I’m more curious—when it comes to both myself and to others—about WHY people meditate (or do not) than in WHETHER we do it. This startles and irks some. I mean, I’m supposed to be a meditation teacher of some sort. And didn’t I offer this group because I believe meditation is valuable, even that it can change the lives? And shouldn’t those who attend “self-improvement” oriented workshops and classes expect to be told what they should and shouldn’t do, maybe even to be kicked in the pants a little bit? I see a few puzzled or annoyed faces around me, and sometimes feel disappointment from them too. By now I know that some of these folks would like to replace the “should” voice in their head—one that may have been nagging them to meditate for decades—with a “should” voice coming out of my head. It’s a little like a shoplifting kid who’s kind of relieved to be caught because it takes some focus off his own internal guilty voice. And for so many these days, especially the “spiritual-but-not-religious” crowd, meditation is regarded as an essential condition for spirituality. How can I be spiritual if I can’t even get it together to meditate regularly?
So I get it when those relative to whom I’m in some sort of meditation teacher-type role ask me: “Should I do this? Should I do that?” And, sure, if it really is just a practically-oriented question—and I think I’ve got something helpful to say—I just answer the question as best I can. But sometimes the questioning itself seems symptomatic of how complicated and problematic the longing for spiritual instruction—and the desire to BE a meditator—can be. Even those who “know” that enlightenment is a result of unlearning rather than of acquiring more technique or knowledge may seek more and more instruction. Even those who’ve heard the words of wise masters encouraging them to “stop,” and who have marinated in the concept of “beginner’s mind” may hunger for just a little more how-to. There seems to be this highly durable, implicit assumption that in order to make “progress”—in this case spiritual progress—we must gain something we don’t yet have, be it a refined technique, secret mantra, or merit from doing good deeds or being a “good” person. And my sense is this may be especially true of women—so often raised to be pleasers and to suffer from “imposter syndrome.” To be sure, some of the most “spiritually accomplished” women I know have the least confidence in their degree of spiritual evolution, anguishing over being bad meditators even as they read book after book about how to become an expert at it.

There are, of course, lots of perfectly normal, basic “should” questions that arise in the context of meditation groups:
⁃ How should I sit?
⁃ Do I need to meditate at the same time every day?
⁃ Do I need to do sitting meditation or can I just try to get peaceful while riding my bike instead?
⁃ Is it okay if I listen to music while I meditate?
⁃ Should I count when I follow my breath?
⁃ Do I need a space that’s devoted solely to meditation?
And, of course, some such questions really do arise from an ignorant innocence. But being habitually hungry for “shoulds”—for rules and norms and guidance of all sorts—can also be a symptom of something else. For example, a way to perform as a diligent student. Think of that earnest person in whatever class who advertises their enthusiasm by asking questions, sometimes even trivial, obvious ones. I recently found myself in puppy class doing something quite like this. In many teaching-n-learning contexts, this may even be a way to demonstrate respect for the teacher and engagement in the class. In some cases, the student may even trying to develop her own sense of agency as a learner, to “claim an education,” as poet Adrienne Rich put it. In short, expressing curiosity and a desire for instruction can be a way of proving—to ourselves and others—that we’re not just going through the motions but want to do this “right.” And given that so many have tried and failed to develop a meditation practice, this longing to feel that “this time I really mean it” makes tons of sense.
When it comes to offering instructional “shoulds” about meditation, though, as I’ve said, I’m a dud of a teacher, often reminding those in the group of the countless books and videos out there that can provide them with various how-to techniques. Some such techniques are quite elaborate and ritualized, and, I suggest, if that’s attractive to you, then, fine. Some methods involve great bodily discipline and restraint. Some include mantra and others don’t. Whatever. And just in case my ambivalence about technique sounds evasive, consider that nearly everyone who ends up in one of my groups has been “trying to meditate” for years. They’ve already read books, watched videos, and maybe even attended retreats, all without having discovered the MAGIC instruction that will turn them into a meditator and confirm that they’re a genuinely spiritual person. To be sure, some in my groups know far more about the various “rules” associated with this or that meditation technique than I do. In fact, as I’ve said, such things do not actually interest me all that much.
My how-to suggestion then, for anyone who may want it, is really spare, a mere reminder of what they already know to do but have not been consistently doing: “Try following your breath, noticing your thoughts, and letting them go.” And, sure, there are sometimes folks whose frustration with such minimalist instruction is written on their face. “Don’t you know what you’re doing?” they seem to be thinking. “Why are you even here if you’re not going to tell us how to meditate?” And I get it. One of my most powerful early meditation experiences was a weekend retreat led by Tibetan lama—a man of impressive, regal bearing—and, as a Westerner, I gloried in the ritualized extravagance and specificity of it all. It meant MORE to me because of the ceremonial feel, arcane recitations and whatnot. I certainly felt like I got my money’s worth, although, looking back, this experience had no lasting effect on my meditation practice per se.

These days, I’m inclined to compare developing a meditation practice to learning stand-up paddle boarding, an activity I took up recently. I made a conscious choice to start by accompanying a more experienced person, to simply follow along, trying to copy what she did and to accept her bare-bones instruction. “Try pulling the paddle out sooner,” she’d say, or “Maybe if you look at the horizon rather than your feet when you try to stand.” I watched her tumble off her board a few times and tried to imitate her when I too took a spill. Learning stand up paddleboarding this way was a departure for me because, as an introvert, an intellectual, and an over-preparer, my inclination has generally been to learn everything possible about an activity on my own—to suck up as much knowledge as possible—and then maybe set out to do it. One predictable result is that I’ve often stalled out in the preparatory phase, endlessly seeking just one more tip or insight that would—I told myself—ensure my success. Sometimes I was really just persuading myself that I was engaged in an activity without ever getting my feet wet. Partly because so many of these activities were overdetermined for me—for instance, I’d thought of mountain-biking or backpacking, or even of quitting smoking, as being really hard—I was happy to do them without, you know, actually doing them. And while I never succeeded at some of these activities, I also never had to experience failing at them either.
In this one respect, at least, getting serious about having a sitting meditation is more like approaching an extreme sport than like paddleboarding: It is not for the faint of heart. Although there have always been those who disparage meditation as “doing nothing,” many—including some who never themselves dare to really try it—sense and fear its awesome potential. Given that much of the point of contemporary society is to help us avoid facing our own internal quiet, sitting down with ourselves is a huge ask, a really daunting prospect. Since many of us—as normally socialized human beings —are effectively addicted to the busy-mindedness of our “normal” lives, asking ourselves to meditate regularly is like proposing an endless series of international flights to a smoker. What this points to, I think, is that many who dance around the edges of developing a meditation practice—making excuses and remaining in the preliminary phase—may be the very ones who most sense its potential and power. Even if they would prefer for now, say, to continue acquiring new information and techniques—still they are drawn to the practice. And so I have an almost perverse respect for some of these dilettante meditators because I think they get it. They may not be ready to transform their lives through this practice, but they often sense that that’s where this meditation-path might lead. They are like a secret admirer struggling to work up her courage to approach the one she loves from afar. Her caution and distance aren’t born of ambivalence but precisely from its opposite, the knowledge that this is a relationship with the potential to upend her entire life.
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