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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Season 2: Trailer
Welcome to Season 2 of The Work of You—the podcast about the leadership that matters most, the kind that starts from within. In Season 2, we’re expanding the conversation. Alongside solo reflections, I’m also sitting down with leaders, coaches, and change agents who are doing the real work—inside themselves and in the world—to explore what growth, self-awareness, and leadership actually require.
This is about noticing the patterns shaping your choices and learning how to lead with more clarity, integrity, and alignment. If you’re a high-achieving human who’s ready to get honest about the patterns holding you back, this show is for you. Because this isn’t about fixing yourself. It’s about finally understanding yourself so your choices, relationships, and leadership actually align to who you really are.
Join us for Season Two of The Work of You starting Wednesday January 14th.
Ep 30: Season 1 Wrap Up - Let’s Celebrate The Wins!
What has this podcast brought me AND you in 2025?
In this milestone episode, I pause to reflect on what this podcast became in 2025. What started as a curiosity-led experiment grew into a consistent practice of inquiry, meaning-making, and conversation around how we understand ourselves. I share how the podcast AND I have grown and of course, ask you to reflect on the same. I look ahead to what’s coming next. As we move into 2026, this podcast will begin to widen the circle with guest conversations, while staying rooted in the same core questions that have shaped the show from the beginning. This episode is an invitation to pause, integrate, and step forward with intention — together.