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The Upbuild Enneagram Library

Upbuild

Welcome to the Upbuild Enneagram Library. We’re glad to be on this journey with you.

We’re two former monks, a former startup founder and CEO, and a former investment bank executive…who met in a NYC monastery. 

Over the past two decades, we’ve used the Enneagram to help countless individuals and organizations see themselves more clearly and start to break free from the shackles of the ego.

Drawing on years of teaching, coaching, and lived experience, we’ve created this podcast as a deep library of Enneagram knowledge to support you in the most meaningful journey there is: the journey from the ego to the true self.


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  • 20 episodes
  • fortnightly
  • Avg 43 min
  • English
  • #39
    September 23 · 30 min

    Type 8 Across the Dimensions of the Enneagram

    This compilation episode brings together our discussions of Type 8 across the many dimensions of the Enneagram to build a richer, more complete understanding of the Type. The team explores the 8’s connection to the Body Center, its relationship with anger, its search for strength, autonomy, and protection, Behavioral Patterns, Wings, and patterns of growth and stress. They examine both the remarkable strengths of Type 8 and the internal struggles that can accompany the pursuit of power, protection, and independence, including the suppression of sensitivity, difficulty accepting vulnerability, and the challenge of allowing others to care for and protect them. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

    • Transcript
  • #38
    September 16 · 33 min

    Type 7 Across the Dimensions of the Enneagram

    This compilation episode brings together our discussions of Type 7 across the many dimensions of the Enneagram to build a richer, more complete understanding of the Type. The team explores the 7’s connection to the Head Center, its relationship with fear, its search for happiness and freedom through experiences, Behavioral Patterns, Wings, and patterns of growth and stress. They examine both the remarkable strengths of Type 7 and the internal struggles that can accompany the pursuit of stimulation, pleasure, freedom, and positive experiences, including anxiety, avoidance of pain, difficulty going deep, and the challenge of becoming grounded and present rather than continually seeking the next experience. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

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  • #37
    September 2 · 39 min

    Type 6 Across the Dimensions of the Enneagram

    This compilation episode brings together our discussions of Type 6 across the many dimensions of the Enneagram to build a richer, more complete understanding of the Type. The team explores the 6’s connection to the Head Center, its relationship with fear, its search for trust and certainty, Behavioral Patterns, Wings, and patterns of growth and stress. They examine both the remarkable strengths of Type 6 and the internal struggles that can accompany the desire for security, guidance, loyalty, and support, including anxiety, self-doubt, and the challenge of learning to accept uncertainty and trust one’s own knowing. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

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  • #36
    August 26 · 35 min

    Type 5 Across the Dimensions of the Enneagram

    This compilation episode brings together our discussions of Type 5 across the many dimensions of the Enneagram to build a richer, more complete understanding of the Type. The team explores the 5’s connection to the Head Center, its relationship with fear, its drive for knowledge and objectivity, Behavioral Patterns, Wings, and patterns of growth and stress. They examine both the remarkable strengths of Type 5 and the internal struggles that can accompany the pursuit of understanding, expertise, independence, and certainty, including the tendency to withdraw from the world and reject the heart in favor of knowledge and facts. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

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  • #35
    August 19 · 37 min

    Type 4 Across the Dimensions of the Enneagram

    This compilation episode brings together our discussions of Type 4 across the many dimensions of the Enneagram to build a richer, more complete understanding of the Type. The team explores the 4’s connection to the Heart Center, its relationship with shame, its search for authenticity, Behavioral Patterns, Wings, and patterns of growth and stress. They examine both the remarkable strengths of Type 4 and the internal struggles that can accompany the pursuit of originality, depth, beauty, and a sense of being truly understood. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

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  • #34
    August 5 · 49 min

    Type 3 Across the Dimensions of the Enneagram

    This compilation episode brings together our discussions of Type 3 across the many dimensions of the Enneagram to build a richer, more complete understanding of the Type. The team explores the 3's connection to the Heart Center, its relationship with shame, the search for value through validation, Behavioral Patterns, Wings, and patterns of growth and stress. They examine both the remarkable strengths of Type 3 and the internal struggles that can accompany the pursuit of success, recognition, and authentic self-worth. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

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  • #33
    July 29 · 19 min

    Type 2 Across the Dimensions of the Enneagram

    This compilation episode brings together our discussions of Type 2 across the many dimensions of the Enneagram to build a richer, more complete understanding of the Type. The team explores the 2’s connection to the Heart Center, its relationship with shame, its drive to serve, its movement in growth and stress, the challenge of accepting personal needs, and the transformational movement from pride toward humility. They examine both the remarkable strengths of Type 2 and the internal struggles that can accompany the pursuit of connection and intimacy. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

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  • #32
    July 22 · 34 min

    Type 1 Across the Dimensions of the Enneagram

    This compilation episode brings together our discussions of Type 1 across the many dimensions of the Enneagram to build a richer, more complete understanding of the Type. The team explores the 1’s deep desire to live according to higher principles, as well as their relationship with anger, perfectionism, activism, the Inner Critic, Wings, and patterns of growth and stress. They examine both the remarkable strengths of Type 1 and the internal struggles that can accompany the pursuit of goodness and integrity. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

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  • #31
    July 7 · 37 min

    The Achilles Heel of Every Enneagram Type (And How to Heal It, Including The Five Stages of Grief)

    What is the one thing about yourself that you cannot accept? In this episode, Michael, Hari Prasada, and Rasanath introduce the Upbuild original concept of the Achilles Heel. Drawing from years of study and teaching of the Enneagram, they explore how each Type has a specific vulnerability it unconsciously resists accepting, and how that resistance becomes the source of suffering and disconnection. They explore how denial and anger often emerge when we encounter it, and the path to acceptance additionally aided by understanding the five stages of grief. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

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  • #30
    June 23 · 42 min

    The Passions and the Virtues

    What keeps each Enneagram Type trapped, and what helps it move toward freedom? In this episode, Vipin, Hari Prasada, and Rasanath explore one of the deepest dimensions of the Enneagram: the Passions and the Virtues. Drawing on the work of Oscar Ichazo, the Desert Fathers, and modern Enneagram teachings, they explain how each Type has a characteristic form of suffering called a Passion that reinforces the ego structure, and a corresponding Virtue that opens the way back to the true self. Through examples and reflections, they unpack why the Passions often remain hidden in plain sight and how the Virtues offer a practical path toward growth. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

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  • #29
    May 12 · 33 min

    The Imbalances of the Centers of Intelligence

    In the Enneagram, there are some Types that disassociate from their Center of Intelligence and other Types where one Center “enslaves” another. Which pattern do you fall into, and what is actually happening beneath the surface? In this episode, Michael, Hari Prasada, and Rasanath explore the concept of the Imbalances of the Centers. They break down the mechanics behind the first and second imbalances and how these patterns form unconsciously. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

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  • #28
    April 21 · 42 min

    The Harmonics: How Each Enneagram Type Approaches Conflict

    One of the most overlooked dimensions of the Enneagram is how we handle conflict. In this episode, Michael, Hari Prasada, and Rasanath explore the three Harmonics: Competency, Emotional Realness, and Positive Outlook. Each represents a distinct strategy for restoring harmony, yet each can just as easily create more disconnection when singularly used or distorted. They unpack how each Enneagram Type leans on one of these approaches, how that strategy breaks down at lower levels of awareness, and why relying on just one Harmonic leaves conflict unresolved. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

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  • #27
    April 7 · 44 min

    The Inner Critic: The Mouthpiece of the Ego

    We live in a constant negotiation with an Inner Critic that tells us we are not enough. In this episode, Vipin, Hari Prasada, and Rasanath shed light on the Inner Critic as the mouthpiece of the ego. Using the Enneagram, they show how this voice operates differently across the Types and how it’s rooted in our Basic Fear, continuously pushing us to become someone we think we should be. They introduce the idea of the Inner Critic game, where we are perpetually earning and losing points based on how well we meet our ego’s expectations. From perfectionism to performance-driven validation, this system quietly shapes our thoughts, behaviors, relationships, and culture, forever creating a heightening tension, and at best, the sense of never quite arriving. This episode is not about silencing the Inner Critic. It’s about understanding it, seeing the patterns more clearly, and beginning to work with it by greater awareness, compassion, and newfound freedom. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

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  • #26
    March 24 · 55 min

    The Shock Point and Red Flag Fears: What Makes Us Slip Down the Levels of Consciousness

    This episode introduces the Transitional Fears, the fears that arise at key thresholds between Levels of Consciousness. Vipin, Hari Prasada, and Rasanath show how these fears are expressions of deeper existential anxiety, why they feel so convincing, and how recognizing them can help you interrupt the ego’s patterns and return to a more conscious way of being. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

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  • #25
    March 10 · 59 min

    Parental Orientation: Attachment, Frustration, and Rejection in the Enneagram

    Every Enneagram Type carries a specific relationship to nurturing and protective energy. That relationship begins in childhood, but it does not stay there. In this episode, Vipin, Hari Prasada, and Rasanath unpack Parental Orientation, the Object Relations framework that explains attachment, frustration, and rejection across all nine Types. They explore how each Type internalizes the nurturing and protective functions and how those early adaptations shape adult behavior, leadership style, relationship patterns, emotional tone, and even our unconscious bias toward strength and softness. By mapping the three relational stances onto the Enneagram, they reveal a precise psychological matrix that helps explain why we seek certain energies, resist others, and feel chronically disappointed in specific ways. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

  • #24
    February 24 · 1 hr

    Falling in Love with Every Enneagram Type

    How do we fall in love with the Enneagram Types? In the same way we fall in love with people in real life: by understanding both their gifts and their suffering. In this episode, Michael, Hari Prasada, and Rasanath explore what it truly means to fall in love with every Enneagram Type. They introduce the idea of “access points,” the doorways that allow us to move beyond intellectual understanding and into genuine compassion for each Type’s lived experience. Moving through all nine Types, they highlight what makes each one uniquely and deeply lovable with the pain they carry. From the Type 1’s longing for purity to the Type 9’s desire for harmony, the conversation reveals how every Type conveys an attempt to cope with their distinct core wounds in an ego-driven world that constantly triggers them. The episode closes with a reflection on why authentic Enneagram work must be rooted in love, and how falling in love with the Types supports spiritual growth, compassion, and our capacity to serve others more fully. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

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  • #23
    February 10 · 57 min

    The Predominant Emotions: Anger, Shame, and Fear

    Each of us lives from one of three distinct inner stances, yet hardly ever realizing it… “Don’t mess with my world.” “See me the way I want to be seen.” “What can I trust?” In this episode, Michael, Hari Prasada, and Rasanath explore how Anger, Shame, and Fear function as the Predominant Emotions of the Enneagram (and of the human condition). These emotions correspond to the Body types (8, 9, 1), Heart types (2, 3, 4), and Head types (5, 6, 7), and point to the deeper forces shaping how we experience ourselves and the world. More than surface-level feelings, they reveal what the ego is organized around and what it is constantly trying to manage or avoid. Moving through the three emotional triads, they explore what provokes each emotion, how it is experienced internally, and how it shows up externally. The gift we stand to gain through this knowledge is the freedom to act differently, instead of being habitually forced to act on the emotion. That’s a lifelong pursuit of self-awareness and self-regulation. But by understanding these emotions, where they come from, why they affect us, and seeing their specific hold on us personally, we can become so grounded and judicious in how we respond to them. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

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  • #22
    January 27 · 41 min

    The Wings

    The Wing is one of the most powerful forces shaping personality. In addition to the primary Type, it strongly influences what we want, how we show up, and even whether we experience ourselves as more introverted or extroverted. In this episode, Hari, Michael, and Rasanath explore why identifying the correct Type-Wing relationship is essential for accurate typing and meaningful growth. Moving through all nine Types, they show how different Wing combinations create distinct energies, body language, and ways of engaging with life. Special attention is given to Wings they see creating a more prominently polarizing effect, where opposing orientations can feel like two very different people living inside one personality. Throughout the conversation, they emphasize how understanding Wings helps us recognize ego patterns, honor our gifts, and engage in the deeper work of self-realization. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

  • #21
    January 13 · 57 min

    The Behavioral Patterns: The Go-Getters, the Withdrawns, and the Dutifuls

    Do you tend to push forward and make things happen? Pull back and feel easily overwhelmed? Or constantly track how much you are giving so you can be sure you are giving more than you receive? In this episode, Michael, Hari Prasada, and Rasanath explore a core dimension of the Enneagram that is critical in being able to type efficiently and accurately as well as understand better how we show up the way we do and why: the Behavioral Patterns. They unpack the Go-Getter, Withdrawn, and Dutiful triads, three distinct ways we habitually move through the world, relate to others, and respond to stress. At the center of the conversation is the idea of the Ego Boundary – how protected or permeable we are to external demands and internal experience. They explore Solid, Thin, and Perforated Ego Boundaries, and how these shape introversion, extroversion, perceivable sensitivity, and other aspects of how we function. They explain why people within the same Behavioral Pattern are so often mistyped as one another, and why behavior alone can be misleading without understanding underlying motivation. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

  • #20
    Dec 30, 2025 · 48 min

    The Directional Movements (the Lines on the Enneagram Symbol)

    “What are those lines on the symbol?” is one of the questions we get most frequently during our Enneagram workshops. In this episode, Hari, Rasanath, and Michael explore the critical dimension of the Enneagram: the Directional Movements. They describe how each Type experiences stress and growth, clarifying why we sometimes resemble other Types. These movements toward another Type in stress or growth reveal important layers of motivation and insecurity. The conversation highlights why coping is easier, growth includes moving through the shadows of another Type, and understanding this dimension can help prevent mistyping. The team offers a concise tour of what each Type looks like when secure and when overwhelmed. They close by bringing greater focus to the practical and spiritual implications of these movements. Links Enneagram Library Live: Join our bi-weekly conversations and teachings on the Enneagram to help you see yourself, others, and the human condition more clearly. Thursdays at 6:15p ET on Zoom. Upbuild Coaching Training Program. Get your ICF certification. Starts in October. Upbuild Website Instagram: @upbuildnyc Facebook: Upbuild LinkedIn: Upbuild

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