The Work of You
This is a podcast about the leadership that matters most — the kind that starts from within.
Hosted by certified behavioral coach and Enneagram expert Jen Ostrich, The Work of You is for high-achieving humans ready to stop repeating patterns and start leading themselves differently.
Through insights from coaching, the Enneagram, and her own personal inner overhaul, Jen brings honesty, humor, and sharp emotional clarity to the table. With real talk, self-awareness tools, and a healthy dose of tough love, she helps you uncover what’s driving you, shift what’s no longer serving you, and ultimately do the work of you — one honest episode at a time.
This isn’t about fixing yourself. It’s about finally understanding yourself — so your choices, relationships, and leadership can actually align with who you truly are.
The Work of You
The Art of Real Connection -- Finding Our Way Back
What if the way back to connection isn’t out there – but in here, in how we choose to show up to one another?
The world feels fractured and more divided than ever before. AND, the technology and algorithms are actually keeping us in separate sandboxes instead of bringing us back together through perspectives and forums of shared connection. This episode explores how we can rediscover genuine connection — with ourselves and others — in a time when the world feels increasingly pulled apart. Jen reflects on the simple yet powerful acts that rebuild trust and empathy, and how connection is at the heart of leadership and personal growth.
Episode topics:
- Why connection matters
- What drives disconnection
- 4 Ways to finding our way back to connection:
- Find + Focus on common ground: through shared values, stories, interests
- Listen over Fix: Building empathy is an invitation to see the world through another’s experience without trying to solve it and instead just sit in it and listen with compassiom
- Ask over Assume: consider asking why or nudge someone to “say more” before you assume and potentially make up your own story that’s not grounded in the truth. This comes down to leading with curiosity and leaving the judgement at the door.
- Self Check: pause and consider how you take in information and is that getting in the way of you connecting with those who operate differently?Enneagram can help here:
- Ex: as a heart type – where are you taking something personally when in fact it’s nothing to do with you it’s about the other persons frame of reference
- EX as a head type – where are you seeking certainty and that’s creating a barrier to seeing another perspective?
- EX as a body type – where are you shutting down or pushing away because difference feels like a threat to your sense of autonomy and agency?
- Takeaways:
- We can’t build trust if we stop talking.
- Connection starts when we choose curiosity over certainty
- When the world feels divided, it’s our small acts of empathy that bring it back together.
Coaching Prompts:
- What would it look like to reconnect with one person you’ve pulled away from?
- What is one small shift you could make to move toward vs further away?
- Take one small action this week to reach out or listen more deeply.
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