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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.
24 Episodes
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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 w...
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 langu...
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 They unpack the Go-Getter, Withdrawn, and Dutiful ...
“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 i...
Each of us is wired with a specific hierarchy of three core instinctual drives, shaping how we move through the world. The Instincts (sometimes referred to as Instinctual Variants) is part of the Enneagram framework and plays a powerful role in how our personalities form. One Instinct tends to dominate and demands most of our attention, a second supports it, while a third gets neglected and becomes a Blind Spot. In this episode, Michael, Hari, and Rasanath unpack the three Instincts—Self-Pres...
There might be a lot going on in your head, but that does not mean that you are making good use of it. In this episode, Michael, Rasanath, and Hari Prasada discuss the Head Center’s essential role in managing the complexity of life and the flood of information we face each day. They explore how awareness of thought, not thinking itself, is the hallmark of presence in the Head Center. They unpack the inner worlds of the Head Center Enneagram Types (Type 5, Type 6, and Type 7), exploring how ea...
Just because you feel a lot does not mean you are present in the Heart Center. In this episode, Hari, Michael, and Rasanath explore what it really means to live from the heart. They look into the realm of emotion, identity, and our longing to be seen. They reflect on how emotions shape our humanity, why we often mistake validation for value, and how the heart connects us to love, gratitude, and one another. They also unpack the emotional landscapes of the Heart Center types (Type 2, Type 3, a...
In this episode, Michael, Hari, and Rasanath turn their attention to the Body Center of the Enneagram. They explore how presence is experienced as groundedness, sensation, and gut-level knowing, as well as how energy can move from intuition into action when we are rooted in the body. The conversation brings out the distinct gifts of Types 8, 9, and 1 while also showing how every Type can cultivate a clearer, more embodied connection to life. Along the way, they discuss the core emotion of the...
Do you really want to settle for being one third of a human? In this episode, Michael, Hari, and Rasanath build off this very provocative question from Russ Hudson to explore the three Centers of Intelligence: the Body, the Heart, and the Head. These Centers help us live with intuition, emotional depth, and clarity of thought. Yet most of us lean heavily on one while undervaluing the others, and even the Center we rely on most is hardly ever one we’re truly present to. We’ll uncover the gifts...
In this episode, we explore how to use the Enneagram in our everyday lives in order to make sure that it has the profound impact on us that it is capable of having. We also discuss how the Enneagram can only take us so far and how a spiritual practice is needed to help us go beyond the limits of our personality. 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 6pm...
Typing is one of the most critical aspects of the Enneagram, and yet, mistyping is rampant. In this episode, we explain why this is case and what we can do about it. We also explore the one Type that is more likely to mistype than any other Type, and give you a Type by Type run through of how each Type approaches the Enneagram. What we find is that how we approach the Enneagram is often very revealing of our Type. Links Enneagram Library Live: Join our bi-weekly conversations and teachings o...
Enneagram Type 9s, nicknamed The Peace-Seeker, pride themselves in being calm, easygoing, and unassuming people who can flow with whatever comes and don’t need recognition or attention. They often don’t admit to themselves their problems or work to resolve conflicts because that’s really difficult and makes them feel not peaceful. Famous examples include Rosa Parks, Grace Kelly, and Jack Johnson. In this episode, we explore the essence of the Type 9 and the insecurities and motiv...
Enneagram Type 8s, nicknamed The Challenger, are all about strength and showing who’s in charge to reassure themselves that they don’t have a weak bone in their body. They often can’t admit to themselves how scared they really are of their buried weakness, and so they show up larger than life in nearly all situations hoping to leverage their power for the people they love. Famous examples include Steve Jobs, Chelsea Handler, MLK Jr, Donald Trump, Aretha Franklin, and Putin. In this epi...
Enneagram Type 7s, nicknamed The Enthusiast, are care-free and fun-loving with a moment-to-moment appetite for adventure and zero tolerance for boredom. They often run from their problems in life which pursue them relentlessly in spite of their intelligence and joyfulness. Famous examples include Robin Williams, the Dalai Lama, Amy Winehouse, and Russell Brand. In this episode, we explore the essence of the Type 7 and the insecurities and motivations that drive their every action and relatio...
Enneagram Type 6s, nicknamed The Loyalist, live in a zone of constant questioning as they strive to be dependable for those they care about. They often wish that they had a cause to dedicate their life to which they could completely trust and that they had the support of others whom they could completely trust. Famous examples include Woody Allen, Adolf Hitler, Jason Alexander, and Larry David. In this episode, we explore the essence of the Type 6 and the insecurities and motivations t...
Enneagram Type 5s, nicknamed The Investigator, are exceptionally cerebral, technical, and keep to themselves in their pursuit of knowledge to understand how things work. They often have trouble relating to people. Famous examples include Albert Einstein, Bill Gates, Eckhart Tolle, Tim Burton, and JRR Tolkein. In this episode, we explore the essence of the Type 5 and the insecurities and motivations that drive their every action and relationship. We walk you through the story of the Type 5’s ...
Enneagram Type 4s, nicknamed The Individualist, try to be authentic with every fiber of their being, but it’s so hard for them to know who they really are deep down. They often feel overwhelmed trying to do justice to their talents, all the while feeling misunderstood by people who move too fast, are too shallow, and act too harshly to understand their full heart. Famous examples include Bob Dylan, Johnny Depp, Prince, Michael Jackson, and Frida Kahlo. In this episode, we explore the essence...
Enneagram Type 3s, nicknamed The Achiever, are smooth and success-driven, endeavoring to show with their life that the sky’s the limit for what can be accomplished. They are also often concerned that others can see through their image. Famous examples include Elon Musk, Oprah Winfrey, Michael Jordan, Barack Obama, Taylor Swift, and Lady Gaga. In this episode, we explore the essence of the Type 3 and the insecurities and motivations that drive their every action and relationship. ...
Enneagram Type 2s, nicknamed The Helper, are all about taking care of others and having deep intimate connections so they can feel really close and loved. They also have a hard time giving others space or seeing their own needs. Famous examples include Fred Rogers, Sally Field, and Stevie Wonder. In this episode, we explore the essence of the Type 2 and the insecurities and motivations that drive their every action and relationship. We walk you through the story of the Type 2’s life by looki...
Enneagram Type 1s, nicknamed The Moralist, are detail-oriented visionaries driven by a set of principles personal that they feel in their gut and want others to align with. They also forever feel the guilt of not living up to these principles themselves. Famous examples include Nelson Mandela, George Harrison, Mahatma Gandhi, Osama Bin Laden, and Queen Elizabeth II. In this episode, we explore the essence of the Type 1 and the insecurities and motivations that drive their every action and re...
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