5 min read

In case you missed it, I recently took part in a 10-day silent meditation retreat. On November 27, I took on the 11+ hour drive through the snow and ice to Shelburne Falls, Massachusetts, to the first Vipassana Meditation Center in North America.

I stayed there for a 10-day course, ending on December 9 (last Sunday) when I drove back.

The response to my original post about going on this trip really surprised me. I can’t believe how many folks responded to my email and social media posts — both folks who have done a course themselves and those who were interested in learning more.

And since I’ve been back, I’ve had a ton of people asking me a lot of questions. Honestly, I’ve probably recapped the experience so many times that it’s mostly rehearsed at this point. But I want to give everyone as much context as possible and share the experience.

So I’m going to give some high level takeaways here, but if you’re really interested in hearing about the experience, I made a couple of things for you.

Here you can watch a vlog the night before starting the program. (10 mins)

Here you can watch a vlog immediately following the program. (43 mins)

You may be thinking those are long videos — and you’re right. But I figured I’d like to have the documentation some years from now, and that I’d give as much context and insight as I could for those who are really interested. The video doesn’t add a ton, so feel free to just listen to the audio in the background.

Coincidentally, Jack Dorsey (founder of Twitter, Square) did a 10-day course at the same time I did at a different center in Myanmar. His tweetstorm overview is a great short distillation of the experience.


  • Headline: I’m glad I did it. I think I benefitted a lot from the experience.
  • I would recommend the 10-day course to others who are interested
  • I was absolutely underprepared for the mental rigor of the course. I kept referring to it as a “retreat” — it was not a retreat. It was a highly-regimented 17-hour day that included 10+ hours of active meditation, beginning at 4:30am every morning!
  • It gave me the ability to access a lot of memories that I thought I had lost. There were days that I literally imagined myself (almost as if a lucid dream) walking through college apartments or the homes of high school friends.
  • Mental determination can be my biggest blessing or weakness. Being my own boss, it’s on me to have a strong determination (or “adhitthana” in Pali) to do the things I tell myself I’m going to do. I noticed at times during the course my propensity to begin to negotiate with myself, and I really spent the majority of the course trying to rewire my mental pattern of doing so.
  • Another ancient Indian (Pali) word that was central to the course was “anicca.” Anicca is the concept of impermanence, or change. The Vipassana technique focuses strongly on this concept, stressing the impermanence of everything as a law of nature. Things come, and things go. 
  • Another core teaching of the Vipassana method was the goal to avoid creating new cravings or aversions (and to over time eradicate existing cravings and aversions). According to Buddha, our tendency to form cravings and aversions for some stimulus is what opens us up to the threat of misery. If we crave something, and it doesn’t happen or go our way, we are miserable. If we are averse to something but are forced to face it, we are miserable. Instead, embrace anicca and realize that all things — pleasant and unpleasant — will eventually fade away.
  • There was a lot of talk and warning of blind devotion without embodying + working to instill the values of beliefs. This is specifically related to dogma of all sectarian religious beliefs. If you want more on this, watch the video.
  • Last takeaway I’ll share here — it was incredibly affirming for how much I love my life. It was a very, very challenging experience — and there were times I felt downright depressed! Being removed from what I know to be a life I’ve designed to be an ideal life was very tough. I was excited to get back to living it.

There’s so much more to share, and I went more in depth in the videos above. Overall, I got a lot out of the experience. It was hard to give a lot of things up for nearly two weeks — coffee, speaking, alcohol, music, technology, etc.

If you are curious to attend a course yourself, you can browse different global centers here. The programs are free and run on donations of past students — so there’s not much of an excuse not to find time if it’s something you’re interested in.

I’m glad to be back and looking forward to 2019. I was also blown away by the response to my 2019 planning sessions, and spent the majority of my week working 1-on-1 with folks who wanted to really dig in and look ahead. It’s been an amazing and fulfilling week.

I’m probably going to make the worksheet/exercise I walked people through available this week for you to self-guide through the exercise without my help. If you’re interested in that, reply to this email and let me know.

PS: We weren’t allowed to bring journals to the course, but around day 4 or 5 I couldn’t take it. I found a dull pencil in the “for student use” supply closet, sharpened it with my nail file, and took a lot of notes on napkins from the food hall the the paper wrappers on the teabags from tea time. Here’s a photo of that mess!