Henry Shukman — Zen, Tools for Awakening, Ayahuasca vs. Meditation, Intro to Koans, and Using Wounds as the Doorway (#531)

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“There’s something about deep wounding that can be a pathway to deep, deep love. It’s a very beautiful thing when the wound becomes the doorway.”

— Henry Shukman

Henry Shukman (@mountaincloudzencenter) teaches mindfulness and awakening practices to a wide range of students from all traditions and walks of life. Henry is an appointed teacher in the Sanbo Zen lineage and is the Guiding Teacher of Mountain Cloud Zen Center. He has an MA from Cambridge and an MLitt from St Andrews and has written several award-winning books of poetry and fiction.

Henry’s essays have been published in The New York Times, Outside, and Tricycle, and his poems have been published in The New Republic, The Guardian, The Sunday Times (UK), and London Review of Books. He has taught meditation at Google, Harvard Business School, UBS, Esalen Institute, Colorado College, United World College, and many other venues. He has written of his own journey in his memoir One Blade of Grass: Finding the Old Road of the Heart, a Zen Memoir.

Henry has also recently created a new meditation program, Original Love, which aims to provide a broad, inclusive path of growth through meditation.

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Stitcher, Castbox, Google Podcasts, Amazon Music, or on your favorite podcast platform.

Brought to you by Allform premium, modular furniture; Pique Tea premium tea crystals (pu’er, etc.); and You Need A Budget cult favorite budgeting app. More on all three below.

The transcript of this episode can be found here. Transcripts of all episodes can be found here.

#531: Henry Shukman — Zen, Tools for Awakening, Ayahuasca vs. Meditation, Intro to Koans, and Using Wounds as the Doorway

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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear another episode with someone who relies on Zen to get things done? Have a listen to my conversation with Zen Habits’ Leo Babauta in which we discuss uncertainty training, embracing the suck, habit breaking and forming, standing out from the competition in a crowded arena, unschooling, and much more.

#488: Leo Babauta on Zen Habits, Antifragility, Contentment, and Unschooling


  • Connect with Henry Shukman:

Mountain Cloud Zen Center | LinkedIn | Facebook | Instagram


  • Why did Henry once identify with Typhon, the mythological beast who lived under the volcano Etna, and how did this lead to his first foray into meditation? [06:13]
  • How examining the deep wound that results from childhood trauma has the potential to become a doorway to deep love (and what so often stops this from occurring). [09:51]
  • What was Henry’s introduction into the world of meditation? [15:19]
  • What does Henry mean by the term “awakening?” [16:40]
  • Is awakening a repeatable phenomenon, or is it something that only needs to occur once? Henry conveys how Zen master Yamada Koun described it, and shares his own first experience. [20:02]
  • Was Henry under the influence of any substances when this happened? In retrospect, what does he think brought it on? [32:12]
  • Was Henry later able to replicate this state of awakening at will, or control it in any way? [36:17]
  • How experimenting with jhana meditation brought Henry to a state similar to what he’d experienced the very first time, and why he thinks this may have happened. [38:10]
  • What happened during the year following that first experience? [40:33]
  • In Henry’s experience, how might an awakening be distinguished from what a psychiatrist with a DSM desk reference might categorize as a psychotic episode? [43:41]
  • Why the modern Western embrace of Eastern spirituality isn’t without its hazards. [46:36]
  • Why awakening doesn’t require us to become hermits and live away from the world, and what Henry learned while roaming the countryside as a teen being mentored by an “old school tramp.” [49:38]
  • What is Zen and how did Henry find it? [54:16]
  • How long was Henry’s first Zazen meditation, and why does he think it moved him so powerfully? [1:01:25]
  • What is a koan? You’re probably familiar with at least one (even if you don’t know how to answer it). [1:02:46]
  • What is nonduality, how do koans guide us toward it, and is the increasing awareness of awakening in the Western world akin to transcending the geocentric worldview that prevailed before Galileo and Copernicus? [1:05:14]
  • Has Henry found it common for Zen practice newcomers to experience a nondual awakening early on? While a psychedelic compound is almost guaranteed to give someone at least a glimpse of this state, how might someone be prompted toward an awakening without it? Additionally, why does Henry consider the term “non-ordinary consciousness” — when applied to an awakened mind — a misnomer? [1:07:59]
  • How awakening can be a “marvelous kind of loss.” [1:15:48]
  • What is Henry’s new program, Original Love, all about? [1:17:59]
  • What does “Mu ichi motsu; muju zo” mean, and can “Koan” be roughly translated as “Over the precipice of nonsense?” [1:20:31]
  • Under what circumstances did Henry make the decision to consume ayahuasca for the first time, and how similar/dissimilar was his experience to koan-induced awakening? How did a later ayahuasca outing under much different circumstances compare? [1:28:24]
  • We ponder how a psychedelic experience might differ from an awakening on a neurochemical level, how each can be useful for exploring different facets of what we perceive as “reality,” and where caution should be exercised. [1:38:46]
  • Has Henry ever witnessed someone having a bad experience through Zen that required special aftercare? [1:43:38]
  • How Zen can be a rewarding journey even without a destination. [1:44:42]
  • Revisiting Original Love: it’s a program, a course, and an upcoming book. [1:46:36]
  • Parting thoughts. [1:47:54]


“There’s something about deep wounding that can be a pathway to deep, deep love. It’s a very beautiful thing when the wound becomes the doorway. I think there’s always that potential with a wound, but so much of the time we tend to accrete protection over a wound and sort of stay away from a wound and avoid it and live as if it weren’t there.”
— Henry Shukman

“There’s another dimension, another aspect, another face of our experience of this very moment in which we are totally part of everything.”
— Henry Shukman

“In awakening, one thing vanishes, that sense of self, and another thing appears, which is what that sense of self was occluding.”
— Henry Shukman

“All space had disappeared. There was no distance anywhere. I felt like my nose was pressing against the end of time. My nose was touching the furthest reaches of the universe because it was all just here. It was one reality without space, without time.”
— Henry Shukman

“I knew that I had found the answer, but I hadn’t even been asking a question.”
— Henry Shukman

“I felt that I had found sort of the answer to life, which I hadn’t been looking for and wasn’t interested in. But now it was like I knew I could die and my life had been fulfilled.”
— Henry Shukman

[On his first experience with Zazen meditation] “It’s not like I had some marvelous enlightenment experience right then, but I did have a sense in that first sit that this was a way of contacting life.”
— Henry Shukman

“The first thing to say about koans is they are not riddles to be solved, and our mind wants to make them that.”
— Henry Shukman

“I suppose I still am a bit of a troubled soul, but I’m a happy one.”
— Henry Shukman

“It’s not like it’s ‘Awakening or bust.’ That’s a wrong mindset.”
— Henry Shukman

“In any level of any zone of practice, love is usually the thing, somehow or other, that triggers the transformation that opens up things.”
— Henry Shukman

“It’s like love to find that we’re part of everything. It’s like love to find that this nothing—no thing—is producing everything, generating everything, infinite generosity. That’s like love.”
— Henry Shukman

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Stitcher, Castbox, Google Podcasts, or on your favorite podcast platform.


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 600 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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12 Replies to “Henry Shukman — Zen, Tools for Awakening, Ayahuasca vs. Meditation, Intro to Koans, and Using Wounds as the Doorway (#531)”

  1. Hi Tim! I’m thrilled to hear you talking about awakening. Last summer I had the silliest “awakening vs. psychosis” story. Basically, something very interesting happened spontaneously, I found a bunch of articles by Sam Harris, Rick Hanson, and other neuroscientists who talk about it, then tried to contact a neuroscientist for a brainscan. I ended up in the hospital with a computer full of articles, a paperback of “My stroke of insight”, then being told “spiritual” experiences don’t exist..

    I would love to hear to hear you speak with Dr. Daniel Ingram and/or Dr. Willoughby Britton, who are both do important work at the intersection of Awakening and “mental health”. The awakening of all sentient beings is an noble goal, but before that it’d be fantastic if we stop locking people up for realizing things and feeling to happy! Love ya bud, thanks for doing what you do.

  2. Tim, can you please get Dr. Thomas Sowell on the podcast? He would be an atypical personality in comparison to who you normally bring on which I think would lead to an incredibly interesting interview. Dr. Sowell is a fellow at the Hoover Institute and a true American treasure.

  3. Dear Tim, I’m grateful for all you do to make the world a better place. I don’t know where else to request an interview, so I’ll say Jane McClelland, author of “How to Starve Cancer ” is tops. She’s my hero, and I went from stage 4 adenocarcinoma to NED in seven months by her method. I made a YouTube video on my journey, and while I think self promotion stinks, I am wanting as many folks affected by Cancer to see it. All the best, Shamus [Moderator: YouTube link respectfully removed from comment to prevent video embed.]

  4. Tim thank you, I am another fan of your body of work it has had significant impact in my life. Looking forward to many more of your Podcasts.

    Guest Suggestion : Mark Epstein, MD Author of “Advise not Given: Guide to Getting over yourself” . He has a blend of Psychotherapy and Buddhist Zen mediation, which provides a different perspective to life and awakening.

  5. I really loved this one….so many things stuck out in my head. Looking forward to the second interview. So glad you are exploring these types of subjects. Thank you!

  6. Your title caught my attention and made me read and listen. Using Wounds as the Doorway is a concept that I connect with. When life knocks you a hard enough blow, you can hold onto that hurt let it make you someone or you can try to grow from it. Also the idea of a troubled but happy soul is inspiring.

  7. Haa thanks for poking around with the questions on psychedlics vs “zen awakening experiences”. Loved what Henry said about them resonating differently because of the fact that you know you have not taken an entheogen. Fascinating field. Life is awesome 🙂

  8. Thank you as always, Tim – just FYI, the correct characters are 無一物無尽蔵; literally (having) nothing, limitlessness/inexhaustible.

    If interested in zen, especially practical zen, stripped bare of complicated monk terms and tradition, I strongly recommend Inoue Gien Roshi’s line – not taught outside Japan, but very recently now translated in English and with English interpretation in Zoom sessions.