My thoughts after a hardcore 5-day meditation retreat.
Not the wind, not the flag; the mind is moving
Last week, I drove to the Hudson Valley in New York State for a 5-day silent retreat. The event was hosted by the Garrison Institute in a former Capuchin Friar monastery that opened in 1932. The retreat featured mostly sitting meditation. You sit there for a total of about eight hours per day, with walking meditation, meals, and one session of yoga mixed in each day. For five days. That’s a lot of sitting. The demographic was much gray hair and bald heads. Montessori vibes. 40% of the cars in the parking lot were Subarus. I shit you not.
As a recreational meditator, the biggest surprise from this considerably more hardcore experience was the incredibly high level of mental and physical difficulty. I underestimated the physical pain of sitting still for so long, and I underestimated the mental challenge that comes with the incomprehensible stretching of time. With no action, no decisions to make, constant pain of varying intensity, limited sensory changes, and zero conversation, time expanded in a way that is hard to communicate without sounding hyperbolic.
Imagine you’re driving 10 miles per hour, for hours straight, in a car with four people you don’t know. Nobody is allowed to talk or make eye contact. Except there’s no car. You’re not moving. You’re just sitting in a meditation hall, staring at the floor. Imagine the most bored you have ever been, for the longest period of time you have ever been bored, and cube it. There are scientific explanations for this severe stretching of time[1], and while I have experienced time dilation of various sorts from stress, drugs, trading, sports, and other activities… This was nothing like any of those. This was, like, one hundred times crazier.
The vibe in the Institute is old wood and dim and quiet. Once the bell rings to signal the start of the vow of noble silence on the first night, you are told not to speak or make eye contact with others. Eye contact is considered “stealing” because it’s a form of communication that disrupts mental silence. It generates unwanted thoughts:
What is he thinking? She looks sad. Why is she looking at me? Etc.
It’s weird at first, but it does relieve you of many pointless thoughts that otherwise would definitely intrude.
Other than the incomprehensible time dilation, the physical pain was the other big surprise to me. You are allowed to change position, but it feels like a tiny loss every time you do so. To change positions, you must bow, reposition yourself, then bow again and get back into the flow of non-thinking. When someone next to you moves, you feel more compelled to move, and knowing this, you don’t want to move because it breaks the overall stillness.
New Mr. Beast video just dropped! 100 meditators sit in stillness. The last one to move wins eternal enlightenment!
At first, I thought maybe I was going to permanently injure my ankles or knees, but then I realized I was far below the median age at the retreat, and many of the others were on retreat number four or five. So, I correctly concluded that the pain was “real”, but not dangerous.
The pain, I learned, also serves a purpose. It keeps you focused on the present as your mind can’t wander to future dreams or past regrets when your knee is screaming in pain. You just focus on the knee and send positive thoughts and inhalations towards it to cool things off. “Pain is a great teacher,” they say, but I was often wondering:
“OK… But what is it teaching me?”
If you think this all sounds a bit joyless, you’re not wrong. It was more suffering than joy, for sure. But much like many hard things, it felt good to go through it and it felt amazing when I got to the other side. And there were bright moments and cool realizations interspersed throughout the discomfort.
For example, the slow passage of time yielded some cool visual effects. You enter the zendo (meditation hall) at 5:50 a.m. each day and take your seat on a cushion. You sit in the same place each day. It looks like this:


When you enter in the early morning, it is almost pitch black. The sun has not yet started to rise, and there is just enough artificial light to see your way around. As 7 a.m. passes, and 8 a.m. approaches, the sun slowly rises and the zendo fills with light. This process is so, sooooooooooooooooooooooooooooooooooooooo gradual. I would watch the shadow of the chair in front of me slowly darken and slide across the room as each second dripped off like molasses. The fluid geometry of the shifting shadows was mesmerizing. Then, as clouds moved in front of the sun and the sun moved across the sky, the patterns of light and shadow would gradually stir and evolve over the course of the day.
As 5 p.m. rolled around, if my brain wasn’t screaming too much in holy agony, I would notice the light slowly disappear from the room like water draining drop by drop from a glass. So slow you barely notice, but since there’s nothing else to notice: You notice. I’ll forever have vivid recall of the way the light and shadows passed through the zendo each day.
Here’s roughly how my brain felt as the retreat progressed. This is an abstract visual representation. The x-axis is not time. Don’t get hung up on the details.

One crazy thought that kept recurring through my seated meditations: “Is that a cat with a butterfly landing on its nose?” For a bit, I thought I was going crazy as there was a smudge on the floor that looked like an image. Or did someone draw an image on the wooden floor in pencil, but make it look like a smudge? No. It was a smudge. After the retreat was over, I asked a woman with a phone to take a picture of the smudge and send it to me. Here it is:


If one were in the meaning extraction business, that would be a strange thing to stare down at for hours on end. But I am a logical human and thus understand pareidolia. Just a smudge on the floor. Definitely not meaningful. Though it did remind me of the 4th Century BCE Taoist parable about simulation theory.
“Once upon a time, I dreamt I was a butterfly… I awoke, and I was myself again. But now I don’t know whether I was a man dreaming I was a butterfly, or a butterfly dreaming I am a man.”
So yes, there were some awkward thoughts about the nature of reality, but let’s move on. My bed was cartoonishly small. Everything smelled of wood and 1950s dust and calm and wisdom. The food was excellent. No chit-chat or small talk—just the taste of the food and the sound of your own chewing… And the odd rogue thought.
So, what was the point?
If the retreat was a lot of physical and mental suffering with deep bouts of the most extreme boredom and time dilation I have ever known… What was the point? Were there any cash or prizes??? Nope. There was no moment where the Brent brain cracked open, the Great Mindflower bloomed, and he saw Nirvana. I did not achieve (or even glimpse) enlightenment. But I am super glad I went. Here’s why:
- There are two types of hard things in life: Hard things with a finish line and hard things with no finish line. Doing hard things, even if they have a finish line, makes me believe I can do other, harder things (including the hardest things with no finish line). When I do 1,000 push-ups in a day, or run a 10k, or read Infinite Jest, or come out on top in business school[2], those are hard things with a finish line. Perhaps completing those things will help me believe that I can do the hard things with no finish line. E.g., maintain an emotionally safe and frequently joyful marriage, be a decent person at least 85% of the time, live with painful loss, and/or successfully manage the demonic internal mind monkeys for one more day. Doing hard things for the sake of doing hard things is not a bad idea. Maybe you can parlay the skills and self-belief into the next, super hard thing?
- My mind needed calming. Sometimes my brain feels like a bunch of 10-year-olds at Toys “R” Us, running around looking for things to play with. Bet on the playoffs! Trade some options! Pitch a USDJPY idea! Go short silver (doh!) Level up in Clash Royale! Get drunk! Listen to a podcast at 3X speed! And so on. Many modules in my brain quickly become agitated if they are not doing something exciting. And it’s easy to confuse fun, excitement, and stimulation with happiness. I thought they were the same thing for many years. As I get older, and I am less concerned about what my 17-year-old self thinks about how cool whatever my current self is doing… I know I mostly want calm, with flurries of excitement. Not constant stimulation with no calm. The silent retreat was a good way to reset a bit and learn to sit with myself without immediately seeking some different way to feel.
Toys “R” Us is fun to visit, but I don’t want to live there.
- No phone! As regular readers know, I dislike smartphones but constantly check mine for no reason nevertheless. With no phone, I feel more peaceful. Maybe I can return to this tech-burdened world confident I can at least go to the bathroom sans smartphone.
- I expect I will never be a monk, and my use of Buddhism will always be recreational. That’s ok. Meditation is daunting! I have had moments in the past where I set a timer to meditate for five minutes and got to three minutes and gave up. Now I know I can sit and meditate for a full hour—without dying! I can meditate for five days! I will meditate more in future. That is good.
- Maybe, just maybe, I can take the lessons of the past week and slow my brain down a bit going forward. Contemplation then action. Not so much reaction.
In many ways, the retreat was the opposite of chasing the night until 5 a.m. when you’re 30 years old. Those nights go by fast, they are chock-full of excitement and stimulation, and all the pain comes later. This retreat went by slowly; it was boring as the sun is sunny; and it will hopefully offer delayed gratification in the days and years to come. Instead of stealing happiness from tomorrow, I am trying to plant a few seeds.
Thank you for reading.
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[1] See, for example: Wittmann M, Otten S, et al., Subjective expansion of extended time-spans in experienced meditators (2015)
[2] I actually finished second in my class. Damn you, Marty Stapleton!!


