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
Summer Listening Guide [S2 Ep25]
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You don't always need a new episode to do new work. Sometimes the most useful thing you can do is go back and actually use what you already heard. This summer, The Work of You is giving you three different ways to slow down, revisit, and go deeper with the episodes that matter most.
This is the Summer Listening Guide — a solo episode designed to meet you wherever you are this summer, whether you're tuning in every week, catching up on episodes you missed, or stepping back from your regular routine entirely. Jen walks you through three ways to stay engaged with your inner work over the coming months: catching up on Season 1 and Season 2 episodes you haven't heard yet, tuning in live as Jen revisits fan-favorite episodes with fresh context from her own life (including turning 50 and a possible big move), and using this episode itself as a standalone journal guide you can return to again and again. August is also an Enneagram deep-dive — the perfect time to learn your type or go further with the model.
In this episode, we explore:
- Three ways to engage this summer: Jen maps out how to keep doing the inner work whether you're listening live, catching up on past episodes, or using this episode as a self-paced journal guide.
- A Season 1 highlight reel: Jen calls out key early episodes — on emotional intelligence, the stories we tell ourselves, communication styles, patterns, and Appreciative Inquiry — and why they're worth revisiting with fresh eyes.
- Journal prompts you can actually use: Each episode highlight comes with specific reflective questions you can work through one at a time, designed to turn listening into real self-leadership practice.
The Work of You - Reflective Prompts:
- What would it look like to invest in your self-awareness? To spend some time prioritizing personal development over professional development.
- How might the story you’re telling be shaping your current actions or reactions?
- What communication pattern can I shift to ensure others hear and understand me?
Resources | Links:
Download this Free Resource: Discover Your Hidden Layer of Leadership
Season 1 Episode 2 |The Leadership Gap No One Talks About
Season 1 Episode 3 | The Myth of Fixing Yourself
Season 1 Episode 4 | Breaking Free from the Patterns That Hold You Back
Season 1 Episode 11 | The Stories We Tell Ourselves
Season 1 Episode 13 | The Communication Patterns You Don't Even Notice
Season 1 Episode 21 | Seeing What's Working via Appreciative Inquiry