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, 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.

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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.


  • Connect with Henry Shukman:

Mountain Cloud Zen Center | LinkedIn | Facebook | Instagram

  • A New Approach to the Ancient Path of Awakening | Original Love
  • One Blade of Grass: Finding the Old Road of the Heart, a Zen Memoir by Henry Shukman | Amazon
  • Other Books by Henry Shukman | Amazon
  • Atopic Dermatitis (Eczema) Symptoms and Causes | Mayo Clinic
  • The Cold War | MI5
  • The Official Secrets Acts and Official Secrecy | House of Commons Library
  • Transcendental Meditation
  • Beatles in India: 1968 Visit to Maharishi Mahesh Yogi’s Ashram | Rolling Stone
  • Waking Up with Sam Harris App
  • Dhyāna in Buddhism | Wikipedia
  • Jhana Meditation | The Contemplative Life
  • Kundalini Awakening: What It Is + 15 Signs You’re Having One | Mindbodygreen
  • What Is Somatic Therapy? | Verywell Mind
  • Keiretsu | Investopedia
  • Why I Wrote a Book about Why I Stopped Writing Books, Part 1 of 2 by Henry Shukman | Mountain Cloud Zen Center
  • Why I Wrote a Book about Why I Stopped Writing Books, Part 2 of 2 by Henry Shukman | Mountain Cloud Zen Center
  • Tramp Stamps Are Making a Comeback | Vice
  • J.D. Salinger and a Zen Koan by Henry Shukman | Tricycle: The Buddhist Review
  • An Insight Meditation Center | Spirit Rock
  • What Is Zen Buddhism and How Do You Practice It? | Lion’s Roar
  • Writing Down the Bones: Freeing the Writer Within by Natalie Goldberg | Amazon
  • Becoming the Mountains and Rivers | Lion’s Roar
  • Zazen Meditation: Benefits, Practice, and More | Healthline
  • Nonduality: Defining the Undefinable | Deconstructing Yourself
  • What Is A Zen Koan? History And Interpretation Of Koans | Being Zen
  • How to Practice Zen Koans | Lion’s Roar
  • 15 of the Deepest Zen Koans | Wisdom Pills
  • The Buddha’s Four Foundations of Mindfulness | Lion’s Roar
  • Message from Henry: Mu Ichi Motsu | Mountain Cloud Zen Center
  • Samadhi: How to Attain It, Stages, and More | Mindbodygreen
  • Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan | Prime Video
  • What is Dokusan? | Lion’s Roar
  • What an Ayahuasca Retreat Showed Me about My Life | Vox
  • Dennis McKenna — The Depths of Ayahuasca: 500+ Sessions, Fundamentals, Advanced Topics, Science, Churches, Learnings, Warnings, and Beyond | The Tim Ferriss Show #523
  • Kenshō | Wikipedia
  • Psychedelic-Assisted Therapy (Resources) | Tim Ferriss
  • Biocentrism: How Life and Consciousness are the Keys to Understanding the True Nature of the Universe by Robert Lanza and Bob Berman | Amazon
  • About Holotropic Breathwork | Grof Transpersonal Training
  • Vipassana Meditation | Dhamma.org
  • The Random Show — Life-Extension Misadventures, Blockchain/Crypto Investing, NFT Experiments, Dogecoin, Zen Buddhism, and Weathering Sharp Elbows | The Tim Ferriss Show #527
  • Immersive Art Experiences | Meow Wolf


  • 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.


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