My Week of Insight Meditation


A few weeks ago, two colleagues from Numinus and I drove down to Barre, Massachusetts for a week-long, silent retreat at the Insight Meditation Society (IMS). Many friends and colleagues were wondering why we would dedicate so much precious time to doing nothing but sitting in silence in the woods. As the week approached, similar questions occasionally crossed my own mind. Now, three weeks after the retreat–with my initial intentions for going clarified and realized–I wanted to explain how a silent week in the woods has profoundly contributed to my well-being.

The IMS approach to meditation focuses on mindfulness as a means of cultivating clear awareness and insight into the causes of suffering, and into the path to well-being. We were guided by two deeply inspiring teachers, Kittisaro and Thinassara, 2 former Buddhist monks who teach at their hermitage in South Africa. Our retreat was loosely structured around three themes, unfolding chronologically: 1) calming the mind, 2) finding insight in what is present, and 3) cultivating wisdom and compassion.

Calming the Mind

Easier said than done! I was coming off a very busy week at work. While the natural beauty and serene atmosphere at IMS offered a welcome break from my hectic urban lifestyle, my mind clearly did not get the memo that it was time to slow down. Somehow, I found myself preoccupied with a million things to do (e.g., go for a hike, take a nap, change my shirt, hurry back for meditation). There was an unmistakable but misplaced sense of urgency to get everything done.

I was extremely restless on the cushion, with a horrific case of monkey mind. We did a lot of single-pointed attention meditation (e.g., breath awareness), which is supposed to help bring the monkey to rest. I would close my eyes and meditate with great effort for about as long as I could sit still, which felt like 30 to 40 minutes, but turned out to be more like 10 or 15 minutes. When I would open my eyes to take a break, I would typically see 99 other yogis in total peace. It was pretty discouraging. After the second night, I had an awful dream that my zabuton (meditation mat) had morphed into a vicious creature that was there to distract and torment me while I was trying to spend time with my family. The beast was part gorilla (huge and strong), part spider (nimble and sneaky), and part panther (huge white teeth and piercing yellow eyes). How’s that for monkey mind?!

Early on the second day, Kittisaro spoke to us about the experience of “pleasant abiding.” When the mind finally settles in and begins to resonate with the rhythm of the retreat, you begin to have uncluttered, simple moments of dwelling in the present moment. These moments have a peaceful and rich quality to them. It’s as if when your mind isn’t filled up with stuff, its default mode is a deep but subtle feeling of calm contentment. I don’t know if my mind and body finally caught the rhythm of the retreat, if all the meditating was paying off, or if Kittisaro’s teaching opened the door to that experience for me, but sometime in the afternoon that day, I began to experience brief moments of pleasant abiding. Don’t get me wrong, I didn’t spend the rest of the retreat in a prolonged state of bliss. These were simply moments–like an island surrounded by choppy water. But they offered a door into the next phase of the retreat.

IMS is often described as a “container” for retreats. That is, every detail of the operation (the facilities, the schedule, the meals, the teachings) is carefully designed to support the process of mindfulness, insight, and awakening. For example, there is very little to do or to take care of over the course of the day, aside from meditating. I did have a yogi job (pot-washing) to complete every day at 10:30am and there were some required meditation periods and Dharma talks. But aside from that, there was lots of space for us to come and go as we pleased (for more on the day-to-day reality of the retreat, check out this post by my colleague Sarah).

In this way, the container provides the empty space into which the mind can project its own activity. It provides an extremely rare and valuable opportunity to observe the patterns and tendencies of our minds, without the content (external events, people, activities) that typically triggers our reactions, involves us, and obscures our vision. This unique vantage point allows us to understand our minds and work with our tendencies with our deeper values at heart.

During the second and third days of the retreat, we were encouraged to practice open monitoring meditations (e.g., choiceless awareness) and to explore the recurring themes arising in our thoughts and emotions the rest of the day. As I tuned into my experience more deeply, I was increasingly amazed by how obsessed I was with getting everything in my environment just the way I liked it. Organize the perfect sensory experience at breakfast; choose the hiking path that maximizes exposure to natural beauty without taking too much time; arrive at lunch at exactly the right time so I don’t have to wait in line too long; always walk the quickest, most direct path from my room to the meditation hall. All of these calculations were running constantly in my head, yet they were completed misplaced. There was actually nowhere I needed to be, nothing I needed to do, and no experience that I had to have. On top of that, the obsessive optimizing was deeply familiar to me. That was the mindset I was bringing to my real-life goals (be the perfect psychologist, get everything done, relax with my family in exactly the right way). I had the beginnings of an insight brewing.

When I spoke to Thanissara about it in one of my interviews (brief check-ins with the retreat teachers twice during the week), she was very familiar with this “tendency” and encouraged me to work with it by a) giving it a name (I chose “optimizing mind”) and b) noticing its impact on the rest of my experience. Over the next few days, I became aware of how my optimizing mind was undermining my pleasant abiding. The calculations were overkill; they were distracting me from the simple, natural richness of each moment. Furthermore, even when I was successful in creating the maximally pleasing experience, the enjoyment didn’t last. My mind would quickly move on to plan for the next moment. I was gradually able to see how this habit was not only making me nuts on this retreat, but also how it subtly added extra layers of stress to my life at home. All that effortful striving to get everything in my life just right is ultimately unsatisfying because desires wax and wane, goals shift, and conditions change. I had to find a way to live my life more simply and peacefully.

Wisdom and Compassion

Watching “optimizing mind” unfold in real time was an incredible lesson in dukha, the Pali word referring to the “unsatisfactoriness” inherent in the human condition. The Buddha’s theory was that human suffering arises from our constant desire for control in an impermanent world. We spend a lot of time striving to have things just the way we like them, yet when we achieve a state of control, either the satisfaction is fleeting or the ground shifts again. Freedom from this existential trap requires the capacity to let go of the cravings and tune into the happiness and wisdom available at any given moment.

My new challenge was to find a way to hold my ambitions a little more lightly so that I still have a rich and meaningful life, but am less attached to achieving the perfect outcome. In other words, I wanted to cultivate a new way of relating to not getting my way.

Kittisaro and Thanissara proved to be profoundly inspiring embodiments of this wisdom. We got little snippets of their lives through their Dharma talks over the course of the week. The most poignant example came from the story of their move to their current home in South Africa. Both had been living as monks in Thailand for almost 15 years. They had fallen in love and decided the time was right to leave the monastery and begin a new life. You can imagine how challenging it must have been for them to reintegrate into secular life after living in the jungle for 15 years. Thanissara spoke about going into a grocery store in the UK shortly after leaving and feeling completely overwhelmed. After some period of uncertainty, they eventually decided to establish their own hermitage in South Africa.

It was 1994 and apartheid had just ended. While there was tremendous joy and excitement across the country, the deep divisions among some of its people were surfacing. Several wars broke out, including one close to the area where the hermitage was located. So on top of the difficult personal transformation they were undergoing, Kittisaro and Thanissara invited profound social and political turmoil as well as the brutal suffering of war to their doorstep. Needless to say, they lived some difficult moments fraught with overpowering pain and doubt. However, they stuck with it, learning that the suffering to which they were exposed was nourishing their capacity for compassion and deepening their wisdom.

Kittisaro and Thanissara’s story delivered an important lesson to me. It boggled my mind that they would actually seek out such painful experiences in South Africa. It became clear to me that if I want to relate differently to my own striving, the key would be to open up to the messiness, imperfections, and discomfort of life, rather than trying to avoid them all costs. All forms of suffering, even my bourgeois variety, bring us in contact with the fundamental groundlessness of being, the reality that everything in life is in flux. When everything is going smoothly in life, our desires, preferences, and goals feel very real and important–sometimes so much so that setbacks can be deeply upsetting. The experience of groundlessness affords some psychological distance from these feelings and a broader perspective from which to view adversity with greater equanimity.

In this way, suffering contains the seeds for future insight, compassion, and wisdom. Each moment of disappointment or frustration in our “first-world” lives actually provides an opportunity. It’s an opportunity to let go, to open up, and to see how our resistance to what is already present limits our capacity to abide each moment pleasantly.


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