The leadership conversation nobody else is having.
Most leadership content tells you what to do.
This show asks you to look at who’s doing it.
Every week Jen Ostrich goes beneath the surface of leadership — into the patterns, the blind spots, the unconscious strategies, and the stories leaders tell themselves — to explore what it actually takes to lead well from the inside out.
With honesty, humor, and a sharp dose of emotional clarity, each episode brings you insights from coaching, the Enneagram, and lived experience that you can apply immediately to how you lead, how you show up, and how you understand yourself.
This isn’t about fixing yourself. It’s about finally understanding yourself.
New episodes drop every Wednesday at 6am EST.
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All episodes below
Ep 29: The Inner Patterns of The Enneagram Head Types [5, 6, 7]
What is it like to be an Enneagram Head Type living in a mind seeking certainty and security?
In this episode we explore the Head Center of the Enneagram—Types 5, 6, and 7—who each in their own way seek certainty and create a sense of safety and security. We'll breakdown the core fear, primary motivation and core emotion to be managed for each type as well as how these translates in personality attributes and behaviors. We'll do a light touch on how each of the 3 instincts shade the core type as well as the pathways to growth for each type.
Ep 28: The Emotional Blueprint of the Enneagram Heart Types [2,3,4]
What is it like to be an Enneagram Heart Type moving through the world seeking connection and attention?
In this episode we explore the Heart Center of the Enneagram—Types 2, 3, and 4—whose core drive is to be in connection and to feel seen. We'll breakdown the core fear, primary motivation and core emotion to be managed for each type as well as how these translates in personality attributes and behaviors. We'll do a light touch on how each of the 3 instincts shade the core type as well as the pathways to growth for each type.
Ep 27: Moving Through the World as an Enneagram Body Type [8,9,1]
What is it like to be an Enneagram Body Type processing the world somatically and through instinct?
Kicking off our 3-part series on diving deeper into all 9 Enneagram types, in this episode we explore the Body Center of the Enneagram—Types 8, 9, and 1—whose core drive is to have agency and autonomy over their world. We'll breakdown the core fear, primary motivation and core emotion to be managed for each type as well as how these translates in personality attributes and behaviors. We'll do a light touch on how each of the 3 instincts shade the core type as well as the pathways to growth for each type.
Ep 26: Embracing More Play!
Play isn’t just something fun — it’s a core part of resilience, creativity, and healthy leadership.
In this episode, we explore why play matters for adults, how it expands your capacity to handle stress (hello, Broaden-and-Build Theory), and simple ways to bring more lightness and joy into your daily life. A gentle reminder that doing “the work of you” doesn’t always have to be heavy… sometimes the most profound growth comes from letting yourself play again.
Ep 25: Gratitude + Audience Q&A
Milestone moment reaching episode 25 and perfect timing as it's falling over the week of Thanksgiving. I hold so much gratitude for my listeners and that's why this week I focus on what you want to hear! I've asked what you're curious to learn more about, questions you have, or resources you're looking for. Tune into this episode to hear all the answers and a special announcement for an upcoming Season 2 plan.
Ep 24: Finding Meaning in the Mess
What if our "mess" is not a detour to be taken and instead a doorway to welcome?
In this episode, we explore what it really means to reset the soul when life feels tangled, heavy, or uncertain. Fresh off facilitating Enneagram work at the Soul Reset retreat, I share the themes that surfaced again and again: the surprising power of rest, what renewal actually looks like in real time, and why resilience is less about pushing through and more about softening into what’s true. If you’re navigating a season of complexity or craving a deeper sense of clarity, this episode offers companionship, perspective, and gentle encouragement for whatever chapter you’re in.
Ep 23: How to Earn (and Keep) Trust
What does trust meant to you? What does it look like in practice?
Trust is the foundation of every relationship — and every breakdown. But what “trust” means can look very different depending on your Enneagram type. In this episode, Jen unpacks what each type needs to feel safe and grounded in trust — and what may erode that trust without you even realizing it. You’ll also explore how each type can stretch toward greater openness and how understanding these differences can help any leader or team strengthen their foundation of connection.
Ep 22: Understanding Your Team via the Enneagram
Without system awareness, the person who is the most self aware often feels the most exhausted.
In this episode, we explore how the Enneagram can be used not just for self awareness and growth but also for system awareness -- to understand and support the dynamics of your team. We’ll look at how different core motivations, communication patterns, and instinctual priorities shape how each person shows up at work. You’ll learn how to recognize common tension points, how to create more psychological safety, and how to build a team culture where people feel seen, valued, and able to contribute in their own way.
Ep 21: Seeing What’s Working via Appreciative Inquiry
What if the key to leading change wasn’t fixing what’s broken, but amplifying what’s already working?
In this episode Jen explores how leaders can create a culture of growth by focusing on what’s already working — not just what’s broken. Using the Appreciative Inquiry framework, she walks through the 4D process: Discover, Dream, Design, and Destiny/Deliver, showing how each phase helps teams tap into their strengths, build collective vision, and sustain meaningful change. You’ll learn how shifting from problem-solving to possibility-thinking transforms engagement, connection, and trust — one appreciative question at a time.
Ep 20: Leading with Humanity - Rediscovering the Heart of Leadership
What if the most powerful thing a leader could do wasn't to have all the answers -- but to stay deeply human and authentic in the process?
Leadership isn’t about being perfect—it’s about being real. In this heartfelt conversation, Jen shares stories and lessons on how to lead with empathy, curiosity, and courage, even when the world feels uncertain. Learn how human-centered leadership can transform not only your team but the culture you create together.
