A Guide to Your First Retreat

The 10-day Vipassana retreat. Where your annoyingly calm, pseudo-enlightened friends go and then return with stories of both monumental struggle and illuminated insight. Perhaps you are curious or perhaps you no longer refer to these individuals as friends. Both positions are understandable. However, the purpose of this article will be to speak to those who have decided that they too would like to sit in pain for many days. This article is not an attempt to convince anyone that a retreat is a good idea but rather it’s aim is to help those first-time retreat goers by shining a light on some issues that will most likely come up during the first few days.

Below I have noted some of the difficulties I struggled with during my first retreat. While differences in retreat centers around the world could make these points irrelevant to some I can only speak of my own experience. However, many of these points will be universally applicable to meditation retreats regardless of where they are taking place. The retreat I refer to here took place at Wat Chom Tong in Chiang Mai, Thailand which is part of a conservative Buddhist temple and follows the meditation practice of Satipatthana Vipassana. Being aware of some of the points I have listed below will undoubtedly make the first days of your retreat go more smoothly. This is by no means an exhaustive list but it does cover a few primary struggles you are likely to face.

It Will Get Weird

Sleeping on the floor. Waking up at 4 AM. Everyone dressed in white. Communal eating halls. No eye contact. No eating after 11 AM. Silence. This is some of what you can expect to encounter during a traditional Vipassana retreat. While it may be embraced by some, the majority of us have difficulty adapting as we realize how wildly different this is going to be from our daily lives. There were times during my first retreat when I struggled to see the difference between where I was and prison. Having never been to prison I concluded that the difference lay in my choosing to be there and in the fact that no one appeared to be getting beaten by a metal food tray. Spotting further disparities became challenging. My advice is to stick with the practice, voice any concerns to your teacher, and eventually these issues will either dissolve into indifference or even blossom into blessings. Sleeping on the floor can be quite a humbling, grounding, and Stoic experience as you realize that duvets and pillows are unnecessary luxuries. Waking up before sunrise harkens back to our ancestors and begins to feel natural after a few days. Dressing in white lends some seriousness to the practice that may otherwise be lost if everyone were showing up to the meditation hall in Lululemon pants. Taking a vow of silence forces introspection. And ceasing to eat after 11 AM ends up settling the digestive system. Hunger becomes a non-issue after Day 1.

Judging, Judging, Judging

Are they looking at me? Was that prostration reverent enough? Did I pray enough before eating? Is my timer too loud? Look at this guy, he thinks he’s so spiritual. A retreat will often reveal some of your worst human characteristics, judgement being one of them. It is possible that I’m alone on this one but during my first retreat I found myself being uncharacteristically judgmental of other yogis and, interestingly, somewhat fearful of judgement from them. Though I do believe there is a certain degree of spiritual materialism and narcissism taking place at a lot of retreat centers this is not a justification for judgement and it can hinder your practice if you allow it to. You are likely to encounter dreaded, bearded, guitar playing, hippie types, overly calm, slow-moving, smiley types, and posturing yoga types. Let it all go. Once you peel back the layers of such superficiality you will realize that regardless of outward appearances most are practicing for the same reason: to get to know themselves more deeply.

The Time

As you experience the onslaught of boredom, doubt, and frustration (and you will) the thought of the number of remaining days will certainly enter your mind. This is perhaps the best test of how well your practice is going. Hold true to the Vipassana philosophy and remind yourself that the thought of the remaining days is a future projection and therefore an illusion, albeit a powerful one. It is easy to get carried away by the thought that a week or more still remains especially when you are being tormented by feelings of doubt and anxiety. Now is the time to walk and sit more. You will find that the present moment is the refuge from such thinking.


Of the Five Hindrances, doubt must be the most powerful and is the most important item on this list. Doubt tends to slither silently through the crevices of the mind, planting roots which then grow to contaminate your entire practice. Be very aware of this hindrance during the first few days of your retreat. You are most likely to begin asking yourself questions like, ‘Why am I here anyway?’, ‘Am I practicing properly?’, ‘What is the point of this?’, or ‘Is something supposed to happen here?’ These questions crept into my practice early on and eventually morphed into much larger, angst and doubt filled contemplations about Buddhism, meaning, and life. These thoughts deserve deeper consideration but a meditation retreat is not the time or place and such thinking will eat away at your practice. The best way to confront doubt is to give it another sit. Cease the questioning, acknowledge it as more thinking, walk and sit for another session, and see how you feel. The truth of impermanence will often reveal itself here and you will realize that the doubt has dissipated and you can move on. However, this approach will not always work. It’s only logical that having doubts about the practice will make us not want to practice. At these times, although your teacher may disagree, I think it’s important to check in with yourself. Drop the existential meanderings, if you have them, and remind yourself why you are on retreat. The answer is typically a simple one – ‘I want to get to know myself better.’ It is this kind of simplicity that can promptly dissolve doubt and allow you to return to practice. Doubt can be a serious issue on retreat and is a topic that will be explored further in a future article.

These are only some of the roadblocks that you may encounter on a first retreat and they are often not easily dealt with. A retreat can be a major event in one’s life and therefore is not to be taken lightly. It’s important to speak with your teacher about the issues you are facing and to take seriously the advice being given. You are not unique. The hindrances you will face have likely been faced by hundreds of other meditators. If your teacher is experienced he or she will usually have the best advice on how to overcome them.

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