Podcast Summary: Understanding Taoism with Jason Gregory
New Thinking Allowed Audio Podcast
Host: Jeffrey Mishlove
Guest: Jason Gregory
Date: December 17, 2025

Overview

This rich and engaging interview explores the fundamentals of Taoism, its critique of Confucianism, how it relates to other Eastern and Western philosophies, and the practical implications of living according to Taoist principles. Jeffrey Mishlove welcomes Jason Gregory, a noted scholar, author, and teacher of Eastern philosophy. Their dialogue clarifies the concepts of Wu Wei (effortless action), the Tao (ultimate reality), the yin-yang symbol, and the lasting wisdom of figures like Lao Tzu and Chuang Tzu. Drawing on Gregory’s books and experience, the discussion offers a nuanced lens through which to view personal well-being, culture, and spiritual practice.

Key Discussion Points

1. The Roots and Evolution of Taoism

• Why Taoism Appeals Now

  • There’s growing interest in Eastern spirituality, particularly post-Covid, as more people seek alternatives to Western materialism and individualism.
  • "I don't know if people are disenchanted with the cultures that they are from or what, but there's a lot more attention to [Eastern philosophy]." – Jason Gregory (03:53)

• Taoism in Context with Neighboring Traditions

  • Taoism is compared with Confucianism, Hinduism, and Buddhism; Eastern cultures are generally more collectivist, generating holistic worldviews.
  • Taoism uniquely balances the collectivist and individualist tendencies of East and West.
  • “Lao Tzu kind of challenged that [Confucian] mentality... a good balance between this kind of collectivist and individualistic mentality.” – Jason Gregory (07:17)

2. The Lao Tzu Legend and Social Critique

• Origins of the Tao Te Ching

  • The legend: Lao Tzu, disillusioned with Confucian society, writes the Tao Te Ching before leaving China.
  • The book is both a wisdom text and a critique of socialization and imposed moral orders.
  • "He left the society that he didn't resonate with... it's leaving. He was leaving the guard advice to, you know, understand the Dao... but also understand why are you in this society." – Jason Gregory (08:58)

• Taoist Hermits and Social Withdrawal

  • Hermitage is traditional but not required; Chuang Tzu encouraged being in the world but not of it.
  • “You need to understand... the human condition is to play roles, but not to overly identify with that role as well.” – Jason Gregory (11:36)

3. Unknowability and Paradox of the Tao

• Describing the Tao

  • Anyone who claims to know the Tao does not truly know it—reflecting the paradox central to Taoism.
  • "It's a divine paradox… once we build a language around what the dao is and we reduce it to logic, then we've kind of made an object of it." – Jason Gregory (13:46)

• The Dao and Comparative Mysticism

  • The Tao is likened to “nirguna Brahman” in Hinduism (reality without qualities) and to similar concepts in Kabbalah (“ein sof ur”).
  • The idea of an ineffable, unified, quality-less substratum appears across many philosophies.
  • "When we think about Naguna Brahman, that is like Brahman without qualities... that's about all we can reduce it to." – Jason Gregory (15:17)
  • “You find [the ultimate substratum] within Judaism, you find it within Hinduism, Buddhism, Taoism...” – Jason Gregory (17:27)

4. Taoism versus Confucianism (and Christianity)

• The Carving and Uncarved Block

  • Confucianism: Human nature is rough and must be “carved and polished” through education and ritual.
  • Taoism: Human nature is innately good, the “uncarved block.” Cultivation/socialization distorts fundamental goodness.
  • “Confucius uses the carving and polishing metaphor and Lao Tzu uses the uncarved block metaphor... Lao Tzu says it’s innate within everything as it is now.” – Jason Gregory (20:03)

• Critique of Social Norms (e.g., Foot Binding)

  • Lao Tzu viewed such social impositions as unnatural, advocating a return to authentic being.
  • “A woman shouldn't have to bind their feet. You shouldn't have to abide by man made rules...” – Jason Gregory (22:42)

• Original Sin vs. Fundamental Goodness

  • Confucianism (like Christianity): Humans are born “beasts” or sinners, needing correction.
  • Taoism: Humans are born fundamentally good; it’s society that corrupts.
  • “You’re not an original sinner. You’re perfect as you are. You were always… born perfect, but the world taught you that you were imperfect.” – Jason Gregory (26:43)

  Notable Quote:
  "[Ox Mountain] is the central metaphor for Taoist fundamental goodness: You were a green, lush mountain once, but now you're a barren and desolate mountain because society kind of wore you down." (28:20)

5. Buddhism’s Place Between Taoism and Confucianism

• Original Face and Deprogramming
  • Buddhism recognizes an original, undifferentiated “face,” lost due to social conditioning; the Eightfold Path is a system to “deprogram.”
  • “It’s kind of a system to help you… deprogram you from that socialization process.” – Jason Gregory (30:27)

6. Taoism, Mysticism, and the Occult

• Inner Alchemy, Qigong, and Magical Practices
  • Taoism, like Vajrayana Buddhism and ancient Egyptian mysticism, maintains secret practices.
  • “There’s a penchant for these occult practices that are related to the path of, in some sense, nagong, like, so inner alchemy.” – Jason Gregory (32:33)
  • The philosophy behind the practice is essential, not just the technique.

7. Taoist Simplicity vs. Confucian Education

• Confucianism: Bureaucracy and Learning
  • Valued literary knowledge and social advancement through education.
• Taoism: Simplicity and Natural Ability
  • Valued simplicity, self-sufficiency, innate “li” (the markings or natural grain in wood), and “ying” (mutual resonance/interdependence).
  • “Education itself is an indoctrination system that can warp your nature... You need to understand what your Li is, and we need to bring that out.” – Jason Gregory (36:14)

8. Effortless Wandering (Xiaoya Yu) & Wu Wei

• Effortless Wandering (Xiaoya Yu)

  • Living with mental and practical ease; “aimless roaming” or moving through life without rigid agendas.
  • “It’s this aimless roaming, this fundamental ease you have in your life.” (39:24)
  • Physical travel can help cultivate spontaneity and flexibility.

• Wu Wei (Effortless Action)

  • Acting in flow, with “non-interference;” the state of being “in the zone” parallels athletic and artistic performance.
  • “Once you begin to let go and allow your skill or allow what you've learned to be what it will without your conscious self interfering… you can express your effortlessness…” (43:21)
  • There are two versions: spontaneous Wu Wei (Lao Tzu) and trained Wu Wei (Chuang Tzu). Both are valid.

9. Reality and Identity: The Butterfly Dream

• Chuang Tzu’s Dream
  • The famous story where Chuang Tzu dreams he is a butterfly, questioning the boundaries of reality and self.
  • “He always had a penchant for the non being... he wants to bring you back into a space outside of logic.” – Jason Gregory (51:59)
  • “When there is no more this and that. You see the still point. You see the infinite in all things from the still point of the Tao.” – Jason Gregory (53:06)

10. The Yin-Yang Symbol and Universal Balance

• Ancient Origins & Metaphysics
  • Yin (feminine, passive, receptive, stillness) and Yang (masculine, active, dynamic) are mutually unified opposites, predating Taoism, encoded in the I Ching.
  • Proper balance is essential—both in society and within oneself.
  • “What Lao Tzu recommends… is he says, know the Yang but stick to the Yin.” – Jason Gregory (56:38)
  • “When you have them in perfect harmony... you impregnate the world with something beautiful.” – Jason Gregory (58:20)

Notable Quotes & Memorable Moments

• On the Paradox of Knowing the Tao
  “Anyone who proclaims that they know the Dao doesn’t. And anyone who really knows the Dao would never tell you that they do.” – Jeffrey Mishlove (13:05)
  “It’s a divine paradox… once we build a language around what the dao is… we’ve kind of made an object of it.” – Jason Gregory (13:29)

• On Socialization and Original Sin
  “You’re not an original sinner. You’re perfect as you are. You were always… born perfect, but the world taught you that you were imperfect.” – Jason Gregory (26:43)

• On Wu Wei "Once you begin to let go... you can express your effortlessness... That's what we would call second nature." – Jason Gregory (43:21)

• On Boundaries and Perception
  “Humans, our species specific essence is a flaw because… we discern between this and that and then that creates this illusion in our mind.” – Jason Gregory (51:28)

Timestamps for Segments

• 00:00 — Introduction; societal critique via Taoism
• 03:34 — Jason Gregory’s background and modern interest in Eastern philosophy
• 05:37 — East/West comparisons—individualism vs. collectivism
• 08:27 — The Lao Tzu legend; Tao Te Ching as social/political critique
• 10:15 — Taoist hermits vs. Chuang Tzu's “being in the world but not of it”
• 13:05 — “Knowing” the Dao and its inherent paradox
• 15:10 — Dao and Brahman; metaphysical cosmology
• 17:04 — Kabbalah, Buddhism, and the universal substratum
• 19:24 — Taoism vs. Confucianism in practice and metaphor
• 21:41 — Foot binding: critique of social norms
• 25:47 — Original sin vs. innate goodness; Ox Mountain metaphor
• 29:58 — Where Buddhism fits between Taoism and Confucianism
• 31:29 — Magic, occult, and inner alchemy in Taoism
• 34:26 — Education in Confucianism vs. natural ability in Taoism
• 39:09 — Effortless wandering (Xiaoya Yu)
• 43:09 — Wu Wei (effortless action/non-interference)
• 47:21 — Wu Wei realized through both practice and spontaneity
• 49:49 — The butterfly dream—boundaries and perception
• 54:06 — Yin-yang symbol in Taoism
• 57:48 — The seed of opposites; balancing yin and yang

Tone and Language

The tone is thoughtful, scholarly, yet accessible; Jason Gregory is conversational and enthusiastic, clarifying complex ideas while rooting them in practical examples. Philosophical language is paired with concrete analogies, personal stories, and historical context, maintaining the spirit of authentic Eastern wisdom.

For listeners new to Taoism, this episode serves as a profound, illuminating introduction and a practical guide, blending timeless philosophy with modern relevance.