By Leo Widrich 

Toward the middle of 2017, I found myself in a strange place when I lived in downtown Manhattan, New York, US. I had left my role at the tech startup I’d co-founded six years earlier and was suddenly without much responsibility. The striving nature of the tech world was no longer something I wanted to be a part of, but I didn’t have a good plan for what to do next, either. 

I started spending days on end with friends sitting in meditation, reading books, and coming more and more inward instead of outwardly striving or wanting to succeed. I’d visited Blue Cliff Monastery a number of times over the years, and some of Thich Nhat Hanh’s books—in particular Peace Is Every Step—had changed my life in many ways. I wondered if I wanted to spend a longer period of time at Blue Cliff Monastery to give myself space for further exploration. In the fall of 2017, I joined for what I thought would be the first month of the three-month winter retreat the monks and nuns undertake each year. Instead of staying for a month, I eventually extended to six months, and ultimately stayed for more than a year at Blue Cliff Monastery, and then at a similar mindfulness center nearby. 

Here are ten things I learned from my time in Blue Cliff Monastery:

Happiness is not a state but how we relate to the different states we’re in.

I entered the monastery with an elusive idea to become “free” or “enlightened,” as it had been popularized to me. The more time I spent there, the more I developed an understanding that what these monastics are aiming to cultivate is not any single kind of fixed state, the way I had projected it. Instead, it was the opposite. The intention was to develop a quality of fluidity, one that could wrap around any experience we’re having with a sense of kind awareness. 

This was both painful and a relief. Painful because it meant I had to let go of my fixed belief to attain a perfected, enlightened state, and a relief because it meant that everything I was feeling—my arrogance, my anger, my sadness, my despair, all these emotions—didn’t need to be done away with. Instead, my time there became an exercise in befriending all these states, letting them have space and be heard and ultimately come and go.

Through this befriending process, I also stepped into many traps that in hindsight seem to be common. One in particular was to mistake a stoic, distanced observing of these states for the kind befriending. That distanced observing only mimicked my false display of strength and confidence. And the kind befriending was often unavailable, and I had to take breaks and come back to it without overwhelming myself.

I’m running because I’m in pain; I’m in pain because I’m running.

When I first started living at the monastery, the most painful thing to me was how slow life was. Most days had few things on the agenda other than meals at 8 a.m., 12:30 p.m., and 6 p.m., and meditation practice at 6 a.m., 11:30 a.m., and 5 p.m. In between was sometimes a Dharma talk.

In the midst of all the space and freedom that were opening up during the days, I noticed a strong pull within me to speed things up. I wanted to be going somewhere and doing something. A big reason I was striving, accomplishing, and aiming to be successful as an entrepreneur in the first place was in large part to cover up the pain I had never learned to deal with that was sitting underneath it all. In going through life at full speed, I noticed how this accumulated and added new painful experiences to the already overfilled storage of pain inside my body. It was a classic catch-22, which in hindsight is bringing me tremendous compassion for myself and others who find it so difficult to turn away from the things they know inevitably are causing them further difficulty in their lives.

Taking a foot off the treadmill and being with the pain that’ll inevitably surface takes courage and will inevitably be accompanied by fear. To me, doing so in an environment where others attempted to do the same and wanted to support each other through this was crucial to avoid drowning in what I was finding.

Monk life, as any life, is not a solitary pursuit.

Another misconception I had when I came into the monastery was the idea of the solitary monk living by himself in the mountain or in a cave. I discovered this was not the case at all. The quality of kind curiosity these monks and nuns practice in relationship to themselves is the same quality they aim to offer to each other. Thich Nhat Hanh emphasizes the Sangha and even goes as far as saying “Without a Sangha, you can’t go very far.”

The “monk in the cave” idea had at first appealed to my wounded self that dreaded deep relationships because of the pain I had encountered in this before. Shifting to the exact opposite, to seek out friends and community and to develop a healthy dependence in being with each other, was a big change for me. And yet, the time in the monastery in many ways prepared me to be in closer connection with my partner and friends these days than any other activity ever has.

I’ve since prioritized making and maintaining meaningful friendships more than I ever have in my life. This insight is confirmed by research—not least by Harvard’s largest longitudinal study ever conducted on well-being—revealing the simple fact that “the quality of our relationships matters more than anything else for our wellbeing.”¹

My caveat is that only after we deal with the underlying wounds that nearly always have been created in relationships—especially when we were children—can we enjoy the solid and supportive foundation long-lasting relationships can bring to us.

Meditation isn’t always helpful.

This may be a shock to read in a post about living with monastics, especially one in the midst of a frenzy that meditation is the silver bullet to happiness. Yet, one of the biggest revelations came to me when I looked closely at what meditation was doing for me. I remember sitting on a couch in the dining hall in the monks’ residence and asking one of the brothers, who has become one of my dearest friends today, about what I should do. He asked me a simple question: “Can you follow your breathing?” 

I replied that no, in fact I couldn’t, and I tensed up whenever I tried to put my awareness on my breath. He wondered if I might hold old wounds in that region of my body so I couldn’t relax. From that point on, I started learning about trauma and the body, venturing into the world of neuroscience and discovering much of what I’m doing today in working with others on their emotional resilience.

I de-emphasized meditation for quite a while following that encounter, especially with the awareness of the breathing meditation. This was a huge relief and a reminder that there’s no one-size-fits-all solution when it comes to uncovering our old pains and learning how to build our emotional strength and develop well-being. 

My identities are not me.

After working in tech and building a reasonably successful company by most people’s terms, and then changing gears completely, I was faced with something fascinating. In the monastery, nobody knew me or the company I had co-founded. On top of that, they didn’t care about that at all. It wasn’t that they didn’t care about me as a human, but they cared much less about any of the identities and accomplishments I carried into their spaces.

For the first time in my life, I became aware of the many identities I carried that I had assumed were me. Here is a list of the ones I most identified with: the startup founder, the entrepreneur, the hard worker, the Leo who is completely independent, and the athlete. 

In taking a step back and being among people who were mainly curious about my humanity, meaning how I was feeling and what I was longing for, the painful task of taking down the carefully erected walls and masks I had built around me began. Peeking through all these identities was a person—often a child—who was scared, vulnerable, and insecure.

As I learned to let my humanity, my emotions, my needs, and my longings speak for themselves, instead of my identities, I felt a different kind of strength coming to me. One that was more resilient and less rigid about my views of the world. This remains a work in progress, yet these days I feel more spacious and balanced in relationship to the identities that give me stability and protection at times, while also letting my humanity come through when it feels safe.

I need both more and less than I thought to be happy.

Some people asked me how it was possible to live such a simple life without all the other elements we usually have. My response is that while I’m giving up some elements, I’m also replacing them with others I’m finding more nourishing and helpful.

Here are some things I’ve realized I don’t need so much of to be happy: a fancy New York City apartment, TV, sugar, fancy meals and eating out a lot, traveling to cool places, and buying things.

On the other hand, these are things I’ve realized I need a lot more of and have prioritized since then: friends whom I trust and see regularly, ideally several times a week; weekly scheduled time to look at emotional pain that has come up; play time with other humans without a screen; lazy time; physical touch and intimacy.

I find it important to point out that my intention with pursuing the first list was a very kind one. It was simply that the strategies didn’t bring me the well-being I was looking for. 

Crying builds strength.

Of all the emotions I had never really learned to attend to, sadness and crying probably topped the list. A large part of my conditioning as a man in a conservative, Roman Catholic family consisted of hearing the following versions regularly: 

• Don’t cry, be strong now; you don’t have to cry about this. 
• Just grit your teeth now and get through this. 
• You’re not a baby anymore; you don’t need to cry. (I was maybe seven years old when I heard that!)

This became so internalized that I ostracized people among my peer group for crying, because I saw it as the biggest possible sign of weakness. Combining this with a heavy dose of homophobia in the conservative small town where I grew up (i.e., “crying is gay”), a whole list of other elements of my human experience, including feeling tender and affectionate, and seeking physical touch, became outcast along with crying.

Finding the safety among the monks and other residents at the monastery to reopen the door to crying was healing to me on such a deep level. I probably cried almost daily for six months during that time, and it was a real joy after a while. I cried tears for when I didn’t make it onto the soccer team when I was seven, for when my grandmother passed away when I was thirteen, for breakups that had happened five or ten years earlier, and for many other reasons.

Later on in my therapy training, I learned that crying became a doorway for me to accomplish what researchers call “biological completion.” This means when we don’t really move through emotions present at the time of an experience, they get stuck in our nervous system. Only after we complete the cycle of what happened does our body fully release the traumatic experience and integrate it into our episodic memory with a beginning and end point. As I completed more and more old events in the monastery, a sense of ease and inner space slowly started to take root.

In my work today, where a large percentage of people are men who have similarly difficult conditioning around crying, it’s been one of the most fulfilling moments to witness when they recover the gift of tears back for themselves alongside vast changes of perspective in their lives.

Things don’t change unless I change; or, there are such things as spiritual bypass and spiritual materialism.

I was coming to a place so peaceful and calm that I thought my life would transform from being in that environment. While being there—near the forest, the streams, and the gentle walking meditation paths of the monastery—was a huge relief, it wasn’t enough. After a few weeks, it became clear to me that hanging out and following the structure without fully being in touch with my own pains and truths wouldn’t allow me to change much.

There is even a term for this in the monastery: spiritual bypass. It’s what happens when we follow along with someone or something, like a guru, a master, or a practice, without taking responsibility for the uniqueness of our own situation. I noticed this was, and remained at times, a severe temptation. Letting myself fully float around in the caring presence of others was certainly necessary and healing for me for a time. Yet after a while, I noticed I wasn’t truly in touch with what was going on inside of me, and I realized that only if I turned toward those scary, difficult places inside would I find sustainable well-being.

Another aspect of this for me was to project my past patterns of being a type-A entrepreneur alongside my other identities onto this new environment. How could I meditate the best? How could I stay in the most perfect posture and say the most kind and spiritual things? Those were the kinds of questions my mind naturally produced, as an extension of what I was practicing before.

Later, I learned the term for that way of thinking: spiritual materialism. It’s another way I didn’t fully attend to my experience and patterns, and found it easier to simply re-label things I already knew.

The body, not the mind, keeps the score.

A big aspect of what I thought would happen is that I would have more understanding of my mind. I mainly defined mind as my thoughts and their patterns. I had read so much about mindfulness, mental strength, having a strong mind, and so forth that it ended up centering me around my experience from a heady place. 

The more I spent time with these monastics, the less it was about the mind. Instead, the majority of my healing and revealing experiences started in the body. My tensions, my relaxations, my anxieties, anger, fears, and despair were firmly rooted not in my mind but in my tight or relaxed shoulders; my clenched or open belly; my chest, arms, and legs. This awareness revolutionized how I started to relate to the world. Instead of seeing everything through the lens of my mind and its thoughts, there was an opening to see things through the lens of my feelings and my sensations.

This experience was so touching for me that I’ve since gone on to undertake training in a body-based psychotherapy called Somatic Experiencing that looks at this from a scientific perspective. The books The Body Keeps the Score and In An Unspoken Voice are instrumental for me to deepen my perspective of how our bodies hold the key to both our most joyful, alive moments and our capacity to be with pain.

My conditioning to live in my head and to prioritize my thoughts over my bodily sensations and feelings remains strong. Yet having made more space for these aspects to have a say in my life has contributed meaningfully to the well-being of my life.

There’s such a thing as conscious suppression, and it’s healthy.

One of the most relieving moments that has stuck with me from living in the monastery was when a monk shared the idea of “conscious suppression” with me. He explained that while the intention of mindfulness is to be present with all aspects of our human experience, this isn’t always possible. At times, what is present for us is so painful that we don’t have the capacity to take things in. At these moments, it is okay to occupy ourselves with things that bring us soothing and ease without directly turning toward what is most alive in us.

This was news to me, and it has carried into my life after the monastery. When things get tough to a level that seems overwhelming, it can be a good idea to not force myself to look at what is bringing me pain. There’s a certain truth and gentleness in opening myself to difficulty only when I feel I have the capacity for it. These days, I learn that doing so with a trusted friend or therapist has proven far less scary than my often militant attempts to bulldoze through pain on my own. Finding the balance between when to dip into presence and when to suppress it for a bit is an ongoing exploration.

It’s been such a joyful exercise to remind myself of living in the peaceful community of the monks and nuns at Blue Cliff Monastery. I continue to do my best to cultivate this stillness and mindfulness every day. Although I’ve fallen off the wagon a few times, there seems to be a baseline I can touch back into whenever I remember again. 

¹ www.ted.com/talks/robert_waldinger_what_makes_a_good_life_lessons_from_the_longest_study_on_happiness

REPRINTED WITH THE AUTHOR’S PERMISSION.

Leo Widrich was a tech entrepreneur building Buffer, a $20m+ business, before turning
toward his inner life several years ago. After living in Buddhist monasteries for some years and training as a therapist, he is currently coaching executives and professionals to live the life they choose. His website is leowid.com.