Heath In Pursuit

This week, we explore the world of the Loyalist—the vigilant, courageous, and sometimes anxious soul who craves safety and certainty. Enneagram Sixes are often misunderstood. We’ll look at their inner committee of doubt, their fierce loyalty, and their surprising strength in times of crisis. This is about fear, trust, and finding solid ground within.

Welcome to the world of the Investigator—the thinker, the minimalist, the deeply curious soul who finds safety in knowledge and solitude. In this episode, we unpack the inner workings of Fives: their hunger for understanding, their tendency to detach, and their incredible ability to see what others miss. We'll talk about boundaries, brilliance, and the path from isolation to intimacy.

In this episode, we dive into the heart of the Individualist—the romantic, the artist, the one who feels deeply and sees the world through a kaleidoscope of emotion. Fours long to be seen as original and authentic, yet often wrestle with a haunting sense of not belonging. We explore the gift of their emotional depth, their creative soul, and what happens when longing becomes a lens rather than a l...

They’re polished, driven, and often the ones climbing every ladder in sight. But what happens when the mask cracks? In this episode, we dive into the world of the Enneagram 3 — the Achiever. We explore their greatest strengths, their quietest insecurities, and the engine that keeps them running. We’ll unpack how they show up in relationships, what they fear most, and why their image matters more t...

In this episode, we explore the compassionate and connection-driven world of Enneagram Type 2—The Helper. Known for their generosity, warmth, and deep desire to be loved and needed, Twos are often the emotional glue holding relationships together. But beneath the surface of selflessness lies a complex inner world of motivations, fears, and growth edges. We unpack the gifts, blind spots, and transf...

Meet the Enneagram One—the justice-seekers, the improvers, the ones who color inside the lines (but secretly wish they could scribble outside of them). In this episode, we step inside the mind of the One, where there’s an ever-present voice whispering (or, let’s be real, shouting) about doing things the right way. We’ll explore the beauty of their integrity, the weight of their inner critic, and w...

Welcome to the Enneagram like you've never heard it before! In this kickoff episode of our 10-week series, we dive into what the Enneagram actually is—beyond the internet quizzes and meme-worthy stereotypes. Think of it as part map (guiding your self-discovery), part mirror (reflecting your deepest patterns), and part mystery (because, let’s be honest, humans are weird). We’ll explore its origins,...

Why do we believe what we believe? And what happens when those beliefs are confronted, challenged, or even dismantled? In this episode, we explore the fascinating architecture of belief—how personal experience, culture, and collective narratives shape what we hold as true. We dive into cognitive biases, the role of identity in belief formation, and the psychological discomfort of encountering oppo...

In a world that constantly tells us we need more—more money, more success, more followers, more stuff—how do we break free from the cycle of endless consumption? This episode explores the philosophy of more across cultures, examining how the relentless pursuit of the next thing is shaping our mental health, relationships, and sense of self. We’ll dive into the psychological and societal pressures...

What if The Wizard of Oz were written today? In this episode, Heath explores how L. Frank Baum’s classic tale might be reimagined as a modern political allegory, reflecting today’s biggest issues—economic inequality, misinformation, corporate power, and the struggles of everyday citizens navigating an increasingly complex world. Who would Dorothy represent in 2025? Is the Wizard just another influ...

In a world that never stops moving, stillness has become a lost art. In this episode, we dive deep into why we struggle to be still, how our inability to pause is affecting our mental health, and the fears that stillness often exposes. We explore the constant noise, distractions, and pressures that keep us from embracing quiet moments—and why reclaiming them is essential for our well-being. But st...

In this episode, we dive deep into the concept of becoming anti-fragile—what it is, how it connects to philosophy and spirituality, and why embracing pressure is the key to becoming truly undefeatable. We explore how challenges and adversity don’t just break us down, but actually shape us into stronger, more resilient individuals. Tune in to discover practical ways to grow through life’s toughest...

Have you ever wondered why you see the world the way you do? Why you react to challenges a certain way? Why some decisions feel right and others don’t? Whether you realize it or not, you’re already living by a philosophy—it’s just been operating in the background. In this episode, we break down the two fundamental components of every personal philosophy—metaphysics (how you understand reality) and...

In this thought-provoking episode, we explore the intricate Hierarchy of Language, breaking down how communication evolves from the simplicity of a single word to the complexity of a full narrative. We journey up the linguistic ladder—words, sentences, paragraphs, chapters, and beyond—examining how each layer adds depth, meaning, and nuance to human expression. Along the way, we grapple with the t...

What’s in a name? Turns out, a lot more than you might think. In this episode, we dive deep into the profound power of naming and how it shapes the way we understand ourselves and the world. From the spiritual significance of Adam naming the animals in Genesis to the psychological impact of “naming it to tame it,” we explore how names create identity, connection, and legacy. Discover the untold st...

In this episode, we dive headfirst into the fascinating world of contradictions. What if life isn’t about choosing sides but embracing the tension of opposites? We explore the profound freedom of living in the "yes/and" instead of the restrictive "either/or." From religion's paradoxes to the unexpected wisdom in comedy, we uncover how contradictions challenge our thinking and help us grow. We’ll a...

In this celestial episode, we journey into the enigmatic allure of the stars. Why do they captivate us? From the ancient art of astrology to the timeless questions they inspire, we explore how the stars whisper stories of connection, mystery, and meaning. They remind us of paradoxes—how we are both infinitesimal and infinite, grounded yet longing for the heavens. Join us as we delve into the cosmo...

In The Art of Getting Lost, Heath Hollensbe explores why losing your way might just be the best thing that ever happens to you. From the paradox of control to the sacred teachings of wilderness and vision quests, we’ll unpack the beauty of uncertainty and the power of presence. With poetic reflections, transformative stories, and practical wisdom, this episode invites you to trade fear for curiosi...