A User’s Guide to a Journey Called Mindfulness

Mindfulness meditation is not a one-time thing. You do it again and again. As you keep doing it, a variety of challenges emerge. Here’s some advice for traveling the path of meditation.

It’s a paradox that never goes away. You start meditating because you want to get somewhere to find some improvement, gain some benefits. But if you reach for benefits, as longtime meditator Jessica Morey says, “you can become striving-oriented, obsessed with trying to get somewhere, to gain experiences.” And yet, meditation, like life, can feel like a journey. It may not be clear where you’re going or whether you have a destination at all, and yet you keep going. It’s not a path from A to Z. It meanders, cycles, and circles back on itself. Fortunately, there are fellow travelers in this journey called mindfulness.

As we at Mindful know from speaking with a lot of people, different questions can pop up at different stages of their journey, whether they are dipping their toes in the water of meditation for the first time, starting to make it a bigger part of their life, or have been doing it for many years. And no matter where you are, it always helps to have the attitude of a beginner, humbled by the power of the mind.

Mindful contributor Jonathan Roberts talked to six of our favorite meditation teachers (see below) to gain their insights about the kinds of challenges that people have in adding meditation to their lives. Each of them in their own way emphasized that it can be a trap to keep thinking that you’re trying to get somewhere (see paradox above). As Will Kabat-Zinn put it, “Practice is really all about helping people step out of this kind of linear thinking. Part of what is so refreshing and liberating is stepping out of that mental framework.”

Life is a little bit like walking one of those slacklines that people tie between trees in parks. We’re always balancing things: work, play, health, sickness, our friendships, our families, our love life (or lack thereof). It’s a little (and sometimes more than a little) stressful. As soon as we tense up, the line starts to shake, and we’re more easily thrown off. It gives immediate feedback. Meditation can help us make use of the feedback.

While we’re the first to acknowledge that there is no single predefined meditation highway to travel on—everyone’s experience and circumstances will differ—we’ve explored the kinds of questions we hear from people in different phases and stages in their relationship with meditation practice

The advice on the following pages is from Mindful, sprinkled with some thoughts from the teachers we talked with. Enjoy.

Barry Boyce, Founding editor

A user's guide to mindfulness - illustration of people meditating, others walking

A User’s Guide to Mindfulness: The Start

All of us who have started practicing meditation usually begin for one (or both) of two reasons: we’re in pain or experiencing difficulty, or we want to perform better. The poster-child image of the meditator we see so often—trim and tanned, well coiffed and made up, sitting in perfect posture with a self-satisfied grin on their face—would give you the idea that meditation is like a cookie mold that makes everyone come out the same. That could not be further from the truth.

Part of the beauty of meditation is that it puts you in touch with what’s going on in your mind, and that starts to help you to be yourself. Starting to discover that it’s OK to be who you are, and actually finding a little bit of relief from the harsh critic in your head, is usually what keeps us going in the beginning. After you’ve started meditating, you are still walking that slackline of life—nothing takes that away—but you might have a slightly more confident smile on your face and a bigger laugh when you inevitably fall off.

1) Get Good Instruction

There are many types of meditation and many ways of teaching meditation. Getting sound instruction in the beginning will help you develop good habits. Take care: You’re choosing a healthcare provider for your mind. If you use an app or other digital tool, make sure the teacher behind it has demonstrated experience. Find out why they meditate and see if it resonates with you. If you meet them in person, see if they take an interest in who you are, not just what they have to say to you. A good meditation teacher is a very caring person.

2) Look at the Landscape

Mindfulness is not religious per se. You can practice it in a nonreligious context, a context with a little bit of religion, or in a religious context. As you look at the different types of teachers and places to learn from, over time you can find one, or a mix of several, that suits who you are and where you are in your life. Mindfulness includes finding space in your mind to make your own informed choices.

3) Pay Attention to Your Body

One of the early experiences in meditation tends to be noticing a torrent of thoughts, a waterfall of this, that, and the other thing tumbling through your mind. It’s easy to think your job is to manage it all. That’s where the body comes in handy. You’re breathing, you have senses, your body is always touching some surface somewhere. These sensations help you notice that you are where you are.

4) Be Kind to Yourself

For whatever reason, most of us tend to rip into ourselves when we get some time alone with our thoughts: Why didn’t I? Why don’t I? What’s the matter with me? Meditation puts you in touch with this undercurrent of self-blame and gives you a chance to come back to your breath and to where you are. Notice the subtle sensations in your body that these thoughts can create. At that moment, you can cut yourself a break for being a human being.

5) Don’t Try Too Hard

Since meditation includes instructions to follow, however simple, it’s easy to try so hard to do it “right” that you just give up. Yet it’s the positive experiences—like noticing some peace of mind has quietly crept in—that really keep you going. Just let them happen. Surprise!

6) No Big Deal

One of the most enjoyable aspects of starting to practice meditation is that in those moments when we finally stop trying to be good at it, we get a chance to laugh at ourselves over how hard we try to just be here. Just put one foot in front of the other.

“What is the path of meditation? Your present moment experience. What is your curriculum? Your life, as it is. Not somebody else’s life, not your ideal life–your life.”

Will Kabat-Zinn

“Looking down the road thinking you’re going to get somewhere often causes suffering. When we stop striving for that excitement, we open to the joy of being curious as we explore the journey itself, not reaching into the future, but exploring what is happening right now.”

Judson Brewer
A user's guide to mindfulness - illustration of people walking and helping eachother.

A User’s Guide to Mindfulness: The Middle

When you start something—learning to play an instrument, a sport, a game like chess—it’s usually a little hard at the outset, but if you decide to stick with it, it gets a little better. A few positive experiences motivate you, and quite possibly they uplift you.

As with any new undertaking, you may enter a honeymoon phase: The early stages can be sweet like honey, but they will fade like the waning moon. Everything changes.

If you decide to keep going, inevitably you’ll face the challenges that come with settling down, as in any relationship. If beginning meditation puts you in touch with your mind and helps you start to get to know yourself better, keeping going is about spending serious time with yourself. You may encounter boredom, emotional upheavals, long-term problems you don’t solve—like the pain of a dysfunctional family member, or the fact that money is tight—all the stuff of life. You’re still walking on that slackline, but you might smile about it more.

1) Enjoy Silence

We can often get the benefit of teachers by listening to guided instruction. At a certain point, it’s helpful to also have plenty of time for silence. It’s what the guided meditation is guiding you toward: having some time when you don’t rely on any extra stimulation. If you’ve already been meditating in silence, try to see if longer sessions, or a retreat, works for you. You might be surprised.

2) Find Friends and Community

When you can share space and time with others who are merging meditation with life in the same way, it helps to relieve the burden of meditation being a big personal struggle. If your area has many groups, try them out and see what resonates with you. Maybe something’s happening at your workplace. That’s more common these days, as is finding community online. You can also make friends with people you’ve attended meditation trainings with. Strong bonds can be formed there.

3) Boredom is Fine

It’s OK to just let one moment unfold into the next without something special happening. In fact, boredom in meditation can be a signal that you’re letting go of the craving for constant entertainment. It contains an element of relief.

4) Be Curious About Your Pain

The more you meditate—the more time you spend just being with yourself without a big project or focus—the more aware you become of what lies beneath the surface of your busy mind. You may start to notice fear, anxiety, or other emotions bubbling up more—and your vantage point allows you to peer into them with interest: What are these all about?

5) Seek the Help of Teachers and Guides

As meditation becomes a deeper part of your life, it can help to find someone, or perhaps several people, who are experienced in this practice. Meditation is intimate. It’s not about an idealized, abstract experience. Talking things over with an experienced guide can help you loosen the stuck places.

6) Appreciate Resilience

You’re going to fall off that slackline many times and end up with some scrapes and bruises. But the beauty of meditation is that no matter how many times you get distracted or lost—even if you stop doing it altogether—you can always just come back.

“Mindfulness is self-correcting. When we inevitably go off course, practice helps us see this and adjust. Regular practice brings calm and clarity. We reap the benefits and those we engage with do as well. Over time we see our motivations and intentions and are able to better align with our deepest values.”

Tara Healey

“Challenges are an opportunity to deepen meditation practice. Instead of panicking, we can understand the wisdom of not personalizing everything and look at the larger human picture. Instead of having a why me attitude, we can say, Well, why not me?” 

Sebene Selassie
A user's guide to mindfulness - illustration of people meditating, some juggling on tight rope

A User’s Guide to Mindfulness: More and More Middle

At some point, you may look up and notice you’ve been practicing meditation for quite a while, even years or decades. Maybe your early, wildly exuberant self might have thought that after decades of meditating, you would be, as Will Kabat-Zinn says, “this version of myself where I’m mindful all the time, I speak skillfully to people. I feel happy….”

As this kind of self-improvement mentality gradually falls away, a shift can take place, Caverly Morgan says, from bringing “mindfulness practice into your life to bringing your life into mindfulness practice.”

When life and mindfulness are not seen as so separate, it’s as if we are looking off into the distance to a long and winding road that goes up and down and sideways off into the horizon. Or to put it another way, that slackline we’re on doesn’t appear to be tied to another tree. It just keeps going.

1) Think of Others

If meditation has given you anything to appreciate—if you still have anxiety and all the other struggles, but your relationship to them is not so fixated—you almost automatically want to share that with others. You don’t necessarily need to go out and teach them meditation (for one thing, that’s a challenging job that carries a lot of responsibility), but the very fact that you may be more comfortable in your own skin can help make others more comfortable in theirs, and that kind of benefit can be infectious.

2) Find Ways to Be Helpful

You may be inclined to give people lots of advice, because you feel you see the predicament they’re in so clearly (you’ve been there yourself), but if you’re not careful, you skip over the part where you listen to them, get to know them and where they are. If you skip that, you tend to impose solutions, and that rarely works. If you can be a facilitator, a midwife, maybe you can help someone to discover their own way forward. They may teach you something as well. No one’s an expert where the human mind is concerned: It’s too big a field of study.

3) Don’t Take Yourself Too Seriously

It’s possible that your years of practice and going on retreats has helped give you some more equanimity. Maybe you do have something to offer others. But we’re all still human, no matter how much we’ve meditated, and one thing humans like to do from time to time is make a big deal out of who they are and what they’ve done. Watch out for that.

4) Appreciate Not Knowing

It’s a cliché that the older you get the less you know, but like all clichés, it’s got some real truth to it. Mindfulness meditation is driven forward by insight and curiosity. As you become more and more curious, you continually venture into the unknown. When you feel you know everything, you’re never surprised or awestruck. When you let things emerge and don’t pigeonhole them too quickly, the world is a little fresher and you’re more open to whatever comes next. You’re like a glass that’s always a little bit empty. There’s always room for more life to be poured into it.

5) It’s Not What You Say

At some point, ideas and words matter less. Your way of being and your actions can speak for themselves. You can let meditation techniques fall away and natural mindfulness emerge

“Once you’ve tasted the fruit of some spaciousness and resilience in your own mind–so that your issues are not so acute and your reactivity and stress are lessened–and you find a groove of direct, personal peace, you’re in a better position to help other people.”

Jessica Morey

“A turn can happen, when you are freed to become more inquisitive about the nature of things. You recognize you can take mindfulness to a deeper level–focusing less on trying to fix yourself, instead being more curious about who this you is.”

Caverly Morgan

Teachers We Consulted

Judson Brewer

Neuroscientist, psychiatrist, author. Associate Professor, Director of Research and Innovation, Mindfulness Center at Brown University.

Tara Healey

Founder and director of Harvard Pilgrim Health Care’s Mind the Moment mindfulness program.

Will Kabat-Zinn

Member of the Spirit Rock Center teacher’s council and Board of Directors and teaches meditation retreats nationally and internationally.

Jessica Morey

Meditation teacher and coach focused on ways to bring our meditation practice off the cushion into our relationships and our work.

Caverly Morgan

Founder of Presence Collective, Peace in Schools, and author of A Kid’s Book About Mindfulness.

Sebene Selassie

Brooklyn-based teacher and author who guides people to remember and trust their belonging. She leads classes, workshops, retreats.

read more

Where Does the Path of Mindfulness Lead? 

While there’s no roadmap to wisdom, there is a path to greater perspective, insight, and emotional freedom. Founding editor Barry Boyce calls on his four decades of practice to take us on the journey. Read More 

  • Barry Boyce
  • February 20, 2020


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About the author

Mindful Staff

Mindful Staff editors work on behalf of Mindful magazine and Mindful.org to write, edit and curate the best insights, information, and inspiration to help us all live more mindfully.