In part one of this two-part conversation, we walked along the edge of paradox where effort gives way to ease and the search itself becomes the obstacle. In this second part of my conversation with Zen teacher Henry Shukman, the way begins to reveal itself, not as something we grasp, but something we live. We talk about awakening, the collapse of separation, and what it means to encounter reality directly beyond language, beyond self. And we find ourselves circling the same mystery from different directions, Henry through the Zen path and his app The Way and me through a new project with Rebind, which is a new AI powered dialogue with the Tao Te Ching. Different forms, different longing to meet life more honestly, more fully and more whole.

Discover a Deeper Path in Meditation – Looking for more than just another meditation app? The Way, created by Zen teacher Henry Shukman, offers a single, step-by-step journey designed to take you deeper—one session at a time. Get started today with 30 free sessions!

The Tao Te Ching is one of those books I keep coming back to. Ancient wisdom, wrapped in poetry, that somehow feels more relevant every year. Like this line: “If you look to others for happiness, you will never be happy. If your well-being depends on money, you will never be content.“Simple. Clear. Actually useful.I’ve teamed up with Rebind.ai to create an interactive edition of the Tao—forty essential verses, translated into plain, everyday language, with space to reflect, explore, and ask questions. It’s like having a conversation not just with the Tao, but with me too. If you’re looking for more clarity, calm, or direction, check it out here.

Key Takeaways:

Exploration of meditation and mindfulness practices.
Insights on the nature of thoughts and their observation during meditation.
Importance of a structured approach to meditation.
Personal experiences and reflections on meditation journeys.
Discussion of the “inner radio” metaphor for understanding thoughts.
Techniques for enhancing present-moment awareness through meditation.
The significance of variety in meditation practices to cater to individual needs.
The role of moderation and balance in personal growth, drawing from the Dao De Jing.
The relationship between relative understanding and direct experience in Zen.
The transformative potential of embracing uncertainty and interconnectedness in life.

Henry Shukman is a poet, author, and meditation teacher who has guided thousands of students from around the world through mindfulness and awakening practices. A Zen master in the Sanbo Zen lineage and the spiritual director emeritus at Mountain Cloud Zen Center in Santa Fe, New Mexico, Henry is a cofounder of The Way meditation app and founder of the Original Love meditation program and has taught meditation at Google and Harvard Business School.

Connect with Henry Shukman: Website | Instagram

If you enjoyed this conversation with Henry Shukman, check out these other episodes:

Embrace the Chaos: Finding Clarity Through Meditation with Henry Shukman (Part 1)

How to Find and Follow a Healing Path with Henry Shukman

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Embrace the Chaos: Finding Clarity Through Meditation with Henry Shukman (Part 2)

The One You Feed