Welcome to the new readers joining us! Grateful to have you here.
I’m particularly excited to share this essay because it sits at the intersection of three things I care deeply about: pursuing psychological wellness, embarking on experiences that redefine us, and making meaning in the in between. As I mentioned in my last piece, while I’ll continue to periodically write about our relationship with work, creativity, and the in between, future essays will center around other areas I’m exploring including psychological well-being, human flourishing, and modalities of introspection (e.g., meditation, Internal Family Systems, etc).
I recently attended my first meditation retreat — 10 days of silence and meditating. A lot of meditating. I’ve developed a relatively consistent morning meditation practice over the years, making my way through Headspace and Waking Up (plus a foray into breathwork via Othership and partnering with an embodiment coach). Most meditation apps are designed to teach the most accessible techniques to a broad audience so I’ve largely practiced calming the mind (samatha) and regulating the breath (pranayama).
I’ve always thought of meditation as a solo practice, never considering working with a teacher or seeking a community until last year when a friend offhandedly mentioned she was going on a 10-day Vipassana retreat. I learned the retreats were fully funded by old students who have benefited from the practice and pay it forward to share the experience with others. Intrigued by a meditation practice so impactful that its participants donate their time and money to sustain the centers, I mentally added it to the bottom of my long-running bucket list for future me to look into. At the time though, I was in a very different place in my career, committed to working full-time at startups for the foreseeable future. I figured it’d be years before I’d be able to take 10 days off to meditate.
When the opportunity to go on sabbatical emerged as a result of a company reorg, the unlikely possibility of attending a retreat suddenly became a reality. Going inward for 10 days, unplugging from the day-to-day external chatter, and meditating on what’s next seemed like exactly what I needed at this phase of my sabbatical. Plus, I was drawn to the idea of detaching myself from society for 10 days (or at least the idea of proving to myself I could do it).
Note: If you intend to embark on your own 10-day Vipassana retreat, take my experience with a grain of salt :) Each of us has our own journey to walk. While I hope this essay is a helpful reflection that inspires you to apply to a retreat (or start a meditation practice), it’s not meant to serve as a reference point to set your sights on. If I could give pre-retreat me one piece of advice, it’d be to trust the process, trust your process.
the resistance
Vipassana retreats are known to have long waitlists given high demand and relatively low capacity, particularly as we emerge from COVID, so I anticipated getting into the course would be the hard part. After two attempts to register, I was accepted to the Kelseyville sit in Northern California set to start in mid-August. When I officially committed to attending, I exhaled a sigh of relief and unexpectedly inhaled a feeling of dread.
The feeling of discomfort and resistance that grew with each passing day as we drew nearer to August 15th took me by surprise. Because of how hard it is to actually get into a 10-day course, I knew deep down I wouldn’t decline or postpone my acceptance, but that didn’t stop my mind from wandering towards the possibility every day. Is this the right time go? Should I wait to go in October? What will not talking to anyone for 10 days feel like? Am I ready? What if something bad happens while I’m gone? Should I continue to spend my sabbatical exploring *on* the grid?
As with most meaningful decisions in life, there never seems to be a good time. I had three main hesitancies: missing my partner’s birthday (despite him giving me his blessing knowing how impactful the experience could be), missing 10 days of marathon training, and being away from San Francisco so soon after we’d returned from the east coast. But then I’d remind myself how rare it was to be at a point in my life where I had 10 days to spare and no external commitments holding me back. Will there ever be a better time? What if I let this opportunity pass and never end up making the time for an experience that could change me?
As someone who finds meaning in seeking out hard things, my typical inclination is to lean hard into whatever it is I’m committing to. Rarely do I waver back and forth, contemplating whether I should bow out, so this overwhelming resistance I felt was befuddling. I reasoned the waves of discomfort were partially attributed to the fact I knew how powerful the 10 days could be.
In an attempt to manage the uncertainty, what I did lean hard into was doing as much due diligence as possible. I talked to every person I knew who had done a Vipassana retreat. I read the course website thoroughly. I scoured the internet for reflections and AMAs. While it’s typically a good idea to go into any new experience with some sense of what to expect, I came to realize that in an attempt to feel in control, I’d inadvertently over prepared and seeded one too many expectations. Conversations with friends were most helpful and kept me optimistically committed, but reading reflections from people whose journeys I had no context on led me to compare my process to theirs which of course is expressively not the point of Vipassana or any type of inner work.
I share my headspace leading up to the retreat because the dread I experienced and my attachment to the material world is precisely why it was the right time for me to surrender to the resistance and practice Vipasanna for 10 days. While I love the pursuit of physically intense activities like running marathons and cold plunging, embarking on a mentally challenging experience is a whole different game. But as with most hard things, the only way through was through.
the art of vipassana
The central tenant of Vipasanna is to see things as they really are. The technique is rooted in the Buddha’s teaching of Dhamma, the way to liberation. While Vipassana draws from Buddhist principles, the practice itself is secular and centers around finding answers within ourselves rather than looking to any one deity. Vipassana was reintroduced and popularized by S.N. Goenka starting in 1969 in India.
To see things as they really are is to recognize that there’s an impermanence to everything in life. Change is constant and often, it’s only when we experience an unexpected event that we come to grips with this reality. The practice of Vipassana allows us to experience this truth daily by teaching us the skill of observing the arising and passing of ephemeral sensations in our body, positive or negative, and sit with them equanimously. Every reaction we have is tethered to a sensation in our body — aversion for the negative feelings and craving for the positive feelings.
The negative feelings stem from the mental conditioning (saṅkhāra) we all inevitably face. We experience little “t” traumas and generate saṅkhāra when we suppress or give into our negative reactions. As a result of unprocessed feelings, these experiences live in our body and subconsciously continue to trigger us over and over long after the original event. As we sit with painful sensations, we may begin to crave positive feelings, but the intention is to observe these sensations with equanimity as well. Vipassana teaches us that we have the agency to control the way we react by welcoming all sensations, good or bad, and meeting each of them with non-attachment. The work is about coming out of the old, familiar habit patterns we’ve grown attach to, allowing saṅkhāra living in our subconscious to rise and resolve at the conscious level.
When you commit to attending a 10-day course, you agree to observe noble silence and cease interacting with other meditators — no speaking, no eye contact, no gesturing. It’s intended to create an environment where you’re processing your experience and yours alone.
same day, different day
Each day, we followed the same schedule and practiced a new technique, following the instructions Goenka shared during discourse the prior evening. The course is progressive with the ultimate goal to build our full Vipassana toolkit over the 10 days.
day 0
The retreat begins on Day 0 when everyone arrives at the site and gets settled in. I caught a ride with two fellow meditators who happened to be the most tenured meditators on the women’s side, having attended almost 20 retreats between the two of them. As we drove to the center, I felt myself ease into a feeling of being at peace as I learned about their experiences and commitment to the practice. How easy it is to get caught in our own mental looping and forget that there’s a big wide world out there filled with people who share or once bore similar hesitations, anxieties, and fears.
Once we arrived and checked in, I unpacked and set up my cabin. Knowing that noble silence would soon begin, I ventured out to meet my cabinmates, hoping to get to know them before we lived in silence for the next 10 days. Over dinner, we traded stories about our lives and I felt the second wave of ease settle within me. I was going to be alright. The strong resistance that had been swirling within me in the weeks prior had all but faded.
days 1-3
The first 3 days are focused on laying the foundation for practicing Vipassana and centering your mind. We began with anapana which involves observing the breath coming in and out of your nostrils (Day 1), the sensations that appear in the triangle area of your nose (Day 2), and the subtle sensations on your philtrum (Day 3). Unlike meditations I’d done in the past, this practice was exclusively about observing my natural breathing patterns rather than regulating the tempo of my breaths.
We spent upwards of 10 hours a day meditating — to say I was bored these first few days was an understatement. I spent part of each sit experimenting with the most comfortable and sustainable seating position, oscillating between one cushion, two cushions, and a meditation bench. As I acclimated to the slow pace of life at the center, I found my mind wandering constantly, unsure of what to make of the practices we were doing. Observing the breath coming in and out of my nostrils sounded simple, but my mind seemed to want to do anything but cultivate awareness, drifting off to make to dos lists, plan trips, and visit memories. These first few days were largely spent becoming aware of just how often I’d find myself lost in thought, worlds away from Kelseyville.
days 4-9
On the afternoon of Day 4, the real work began and we started practicing Vipassana. Learning anapana the first 3 days was designed to prepare us for expanding observation beyond our face to sensations throughout our entire body. We began with full body scans and soon, we progressed to developing strong determination (adhiṭṭhāna), sitting completely still for one hour meditations while observing any and all emerging sensations.
As I counted down the days, I began to develop a deep appreciation for the technique. I was met with intense physical pain during many sits as triggering memories washed over me. I learned to welcome and cultivate equanimity over and and over and over. I knew there was a component of sitting still which I had assumed would result in most of the physical pain, but I quickly learned that aside from my leg falling asleep, most of the aching would disappear once I walked out of the meditation hall. While the point of the practice is not to intellectualize the memories flooding back and make sense of them, I couldn’t help but acknowledge how intensely memories from long ago still impacted me. I thanked my younger self for her strength and allowed certain memories to take up space in my consciousness.
During this leg of the retreat, it felt like I had an all-access pass to a theme park, riding the roller coasters of emotion up and down, down and up. Over the final days, I faced a series of setbacks in progressing my equanimity and started questioning the process, feeling a rise in frustration and hopelessness. With no other option than to pick back up, I did all that I could do, gave myself grace, and started again and again and again.
day 10
After an intense few days, arriving at the final full day brought a swell of bittersweet emotions. I was grateful to make it to Day 10 and excited to head home, but the path was turbulent and I sensed it wasn’t quite over. Day 10 is mettā day where we learn the technique of cultivating loving kindness and goodwill.
During our first mettā session that morning, I felt a sense of numbness. Disappointed with the lack of loving kindness alive within me, I stayed in the meditation hall after noble silence broke and most folks left the hall, willing myself to feel something. 10 minutes passed. 20 minutes passed. 30 minutes passed. Nothing. Disheartened, I resigned to the fact that it wasn’t meant to be and left the hall to join the other meditators who had began their reintegration back to civilization.
As I walked out of the hall, I immediately spotted my cabinmates and we spent the next few hours processing the experience together. I slowly felt myself reinflate. Digesting the experience with the other women I meditated alongside for 9 days proved to be one of the most meaningful aspects of the retreat for me. Challenging experiences and unfulfilled expectations can feel so intensely isolating when you’re facing them alone yet, when others let you into their parallel realities, there’s a levity that comes with recognizing that our struggles are not so unique after all.
day 11
While the retreat is 10 days, it doesn’t officially wrap until the morning of Day 11 to allow for a full day of integration. There was a palpable sense of excitement in the air that morning. The morning kicked off like any other at 4:30AM with our last group meditation and then a final discourse from Goenka.
I arrived at the meditation hall earlier than usual to begin the day. Uplifted by the conversations I had the prior day, I had accepted my process for what it was: a practice in progress. My attachment to cultivating mettā had been rooted in the thinking that Day 10 was the final step of the retreat — in actuality, my Vipassana journey was just beginning.
As fellow meditators trickled into the hall, I began to feel an overwhelming sense of gratitude well up in me as I acknowledged that this was the final time this cohort of people would convene for a meditation. I felt deeply grateful for all that we’d faced, alone together, and everything we’d accomplished. The random noises throughout the hall that had previously pulled me out of concentration hit different, comforting me as we concluded our time together. After 10 days of the same routine, the impermanence of it all finally dawned on me.
the surrender: learnings & reflections
Walking into the 10 days, I thought I knew what would challenge me: being without a phone, not talking to anyone, not reading, not working out. I can’t remember the last time I went even a day without reaching for my phone, talking to anyone, reading, or working out, let alone doing all four at once. Turns out, these concerns were secondary to the struggle of non-doing. To eat for the sake of eating, not socializing. To walk for the sake of walking, not exercising. To be for the sake of being, not doing.
To be still with the sensations in our body is an experience we rarely have time and space for. How often do we retreat to the material world for safety and avoid turning inward? We walk around under this illusion that we can change circumstances out of our control and people beyond ourselves yet, the truth is the only thing and person we have the power to control and change is our self. And that change can only happen if we are willing to be still with our self long enough to understand our self.
trust the process, trust your process
Despite my commitment to seeing the retreat through and all my due diligence, I admittedly began the retreat skeptical. I questioned why the retreat was 10 days long, why we needed to abide by noble silence, why we needed to surrender our phones, and the effectiveness of the technique as we progressed from Day 1 to Day 10. Every day, I’d observe doubts floating into my thoughts and wonder if I’d make it to the end of the retreat. In the evenings, we’d watch a 1-hour discourse from Goenka who acknowledged some of the feelings I’d felt that day and prepare us with a new technique or focus for the next day. As Goenka handed us a new puzzle piece each evening, my inner skeptic gradually softened. Day by day, the work, despite it being challenging at times, began to fall into place and I developed a deeper understanding for why I was here.
By Day 6, I felt like I was starting to grasp the technique so when Day 8 rolled around, I was shaken by the feeling that I was regressing. My equanimity was faltering as pain flooded my upper back and shoulder during our group sits that day. I had read a reflection online from another meditator that by Day 7, he could recall previously painful memories without feeling the negative sensations attached to them. So why was I feeling an increase of negative sensations on Day 8? The retreat was nearly over — was this all for nothing? The frustration that stirred in me intensified the throbbing.
In the depths of discomfort, I realized how much weight I was putting in a stranger’s process — I had no idea who this meditator was and what his life circumstances were. With that realization, I began to welcome the pain more compassionately. This too shall pass. As with many experiences in life, it’s easy to anchor to what others are doing and achieving as a reference point in setting expectations for ourselves, but like meditation, no two people come to the mat with the same lived experience. So much of our lives revolve around seeking counsel from others, but when we allow ourselves to be still, we find the answers we seek are within us.
All the conversations I had and research I did was a part of my process, but the danger was allowing others’ processes color my expectations for how my experience would play out. In the end, I needed to experience the technique for myself to truly understand it and release the expectations I had from intellectualizing other people’s stories.
life is a series of experiments
When your to do list each day is meditate, eat, walk, and sleep, you begin to appreciate how slowly time passes. I’ve never been one to wish time away — I’m usually the opposite, striving to make the most out of every moment.
After following the same schedule for a few days, I realized how much room for awareness and experimentation there was. To expand my awareness, I began experimenting with the foods I was eating for breakfast and lunch, observing which hours I seemed most focused, figuring out which break was most conducive to napping, etc.
As I experimented, it occurred to me that our lives are a series of small experiments. We’re met with opportunities every day to tinker and learn something new about ourselves. When we take ourselves and our routines too seriously, we become set in our ways, attached to outcomes and forgetting that it’s all up for negotiation. Every decision we make and every preference we have is simply the result of a data point from a prior action we took. In an effort to optimize and maintain control, we lock in our default settings and move about life unaware of the other choices available to us as our lives evolve.
If you’re feeling stuck in an area of your life, observe the assumptions you’ve made about the particular circumstance and get creative about experimenting with alternative paths. A new approach may be awaiting you just on the other side of experimentation — rarely does life lock us into true finality. When we recognize how much agency lives within us, we can begin to appreciate the impermanence of it all.
be gentle with yourself
One of the best pieces of advice came from my friend, Armand, who embarked on his own retreat several years ago. When I expressed hesitancy about going, he reminded me to be gentle with myself. Ironically, he’s a friend that I enjoy doing hard things with. His point was that my ultimate goal was to survive the 10 days in a meaningful way — just because this was a hard thing didn’t mean I had to stay hardened to how I approached the experience.
Part of being gentle with ourselves is giving ourselves the permission to be gentle with ourselves. This advice came in handy the days I found myself doubting the process. I gave myself permission to be okay with not running for 10 days despite being 2 months out from my next marathon. I gave myself permission to nap more than I’ve napped in my entire adult life. I gave my mind permission to wander, gently redirecting it to observe sensations when I noticed it wandering. I learned to give myself grace when things got hard and the process took “longer” than expected.
the unexpected fruits of our labor
An unintended result of the retreat despite not exercising for 10 days was a significant change in my health metrics while I was at the center. If you know me, you know I’m a health nerd. I wore my Oura ring throughout my time in Kelseyville, curious how my stats might change. While the ring didn’t capture a complete 10 days of data, I have enough data to see meaningfully positive changes that happened as a result of practicing meditation for 8+ hours a day and living in the woods unplugged.
As a reference point, my resting heart rate is typically 48-53bpm and my heart rate variability is typically 60-80ms. As I continue to meditate at home, my Oura ring now often picks up my sits as nap times because of the drop in heart rate during the hour. I’m fascinated by the impact that meditation has on our recovery and overall health — more to come on this topic in a future essay.
A second byproduct of learning Vipassana was discovering my interest in Buddhism. Buddhism’s approach of finding the answers we seek within our inner world resonates deeply with me. When I learned Buddhism a lifetime ago in high school, the teaching didn’t resonate. Now, years later, I’m reminded of the wavering evolution of our interests — all the life I’ve lived has led me to being invested in understanding our human nature.
starting line
I’ll close this reflection with an interesting observation I’ve made about the people I’ve met who practice Vipassana. Prior to their first retreat, most people I’ve talked to have never maintained a consistent 1-hour meditation practice — personally, the most I’d meditated pre-retreat was 45 minutes. Some people go into the retreat having never meditated at all. When we consider committing to a hard thing, we often feel as though we need years of experience and qualifications to earn the permission to try — in actuality, we just need to start somewhere. Anywhere that tests your limits is a worthy starting line.
We have to revisit our edges once in a while to remember the shape of who we are.
— Westley Dang
If you’ve been contemplating attending a Vipassana retreat or visiting your edges in another way, I hope this reflection nudges you one step towards finding the courage to commit. Send me a DM on Twitter if there’s any way I can support you!
Thanks to Ryan & Nancy for reviewing an initial draft of this essay, to Angela, Nancy, & Nicole for making sense of this experience with me, and to Armand, Abhinav, Janelle, Lulu, & Gaby for inspiring me to embark on this journey.
thank for sharing your experience. I find that i am always in my thoughts these days and a silent retreat would be even more detrimental to me LOL Im glad it worked for you though.
Thanks for sharing! Took me back to my experience doing Vipassana a few years ago (wrote about it here: https://ray-h-liu24.medium.com/my-10-day-silent-meditation-retreat-experience-a30ad56703f)