The Work of You

Jen Ostrich
  • 5.0 (23)
  • Self-Improvement

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.

  1. Sep 2

    The 50th Decade — Pausing, Pivoting, and Choosing Me [S2 Ep34]

    Send some fan mail Click Here to Support: *If you're able to support this free independently produced podcast it would mean so much to me * In this solo episode, Jen shares the real story behind a major life decision: selling her home and moving into a new season she's calling her "50th decade." She walks through the framework that got her there — knowing when to pause, when to pivot, and when to proceed — and how each of those shows up differently depending on how you're wired. Jen also gets honest about what's behind the podcast's own pause: a season three that's being rebuilt from the ground up, centered fully on the Enneagram. This is a episode about permission — to change your mind, to prioritize yourself, and to trust your own timeline even when it doesn't look like what you promised. In This Episode We Explore The Pause/Pivot/Proceed Framework: Jen introduces the three-word lens she uses for reading what a decision actually calls for, and how your default wiring can make one of the three harder than the others.Choosing Yourself Without Justifying It: Why Jen decided to sell her home and move — a decision she describes as not needing to make sense to anyone but her.Leading Through an Enneagram 2 Lens: How Jen's Type 2 wiring shows up in the guilt of "letting people down," and what it looks like to keep leading herself through it anyway.What's Ahead for Season Three: Jen shares why the podcast is pausing its weekly cadence, what's coming instead between now and the relaunch, and her vision for a season built entirely around the nine Enneagram types and their subtypes.The Work of You — Reflective Prompts 1. Consider where you might need something that you may not be allowing yourself to fully name or see or accept.  2. Do you need to pause or pivot or proceed around something? Is doing so in service of your needs specifically? Resources and Links Enneagram Type Deep Dive Mini Course- Promo Code: POD2026 (valid through the end of 2026) Download this Free Resource: Discover Your Hidden Layer of Leadership  iEQ9 Enneagram Assessment  The Work of You | Substack  Instagram | The Work of You Website | The Work of You Instagram | Grow Collective Website | Grow Collective Support the show

    The 50th Decade — Pausing, Pivoting, and Choosing Me [S2 Ep34]

  2. Aug 26

    A Koko Birthday Tribute: The 9 Types as Dog Breeds [S2 E33]

    Send some fan mail Click Here to Support: *If you're able to support this free independently produced podcast it would mean so much to me * You already know your patterns show up in how you love, how you compete, how you protect yourself, and how you avoid pain. What you might not know is that they show up in your dog, too. This episode is a tribute to Jen's 15-year-old boy Koko, and a joyful, surprisingly clarifying tour through all nine Enneagram types as dog breeds. In this rerun-turned-tribute episode, Jen celebrates her dog Koko's 15th birthday by bringing back one of her favorite frameworks: mapping the high side of each Enneagram type onto the dog breeds that embody it. She moves through all three centers of intelligence — heart, head, and body — pairing two breeds per type, from the people-pleasing Cavalier King Charles Spaniel of type Two to the no-nonsense Blue Heeler of type One. Along the way, she weaves in stories about her own dogs and the dogs of friends and listeners, using each one as a mirror for the motivations, fears, and gifts underneath the type. It's a lighter entry point into the Enneagram model, but the goal is the same as always: helping you get curious about your own inner drive, not just your outward behavior. In this episode, we explore: The three centers of intelligence: How the heart, head, and body types organize all nine Enneagram numbers, and why the type breakdown moves in that order.The high side of each type: Two dog breeds per type, chosen to capture the different expressions of that type's core motivation and energy.Subconscious motivation over behavior: Why your type is defined by what drives you underneath, not by how you appear on the surface.Wings and lines as a growth map: A reminder that your core type is a starting point, not a box, and that the neighboring numbers and connecting lines show you the path to your most integrated self.The Work of You - Reflective Prompts:  1. Which dog description felt the most like you, and which parts deeply resonated? 2. Was there a dog type or an Enneagram type that you felt resistance to? What might that be telling you? 3. How do you show up when you're at your best? And what kind of dog would that be like? 4. Who in your life might be a totally different dog type, and how does that shape your dynamic? What are some things you might notice between you and another "dog" in your life? Resources | Links: S1 E9: What if the Enneagram Had a Tail? Learn the 9 Types as Dog Breeds Enneagram Type Deep Dive Mini Course- Promo Code: POD2026 (valid through the end of 2026) Download this Free Resource: Discover Your Hidden Layer of Leadership  iEQ9 Enneagram Assessment  The Work of You | Substack  Instagram | The Work of You Website | The Work of You Instagram | Grow Collective Website | Grow Collective Support the show

    A Koko Birthday Tribute: The 9 Types as Dog Breeds [S2 E33]

  3. Aug 12

    Your Enneagram Lines -- What They're Telling You, Part 1 [S2 Ep31]

    Send some fan mail Click Here to Support: *If you're able to support this free independently produced podcast it would mean so much to me * When you're stressed, you don't become a worse version of yourself — you become a predictable one. There's a pattern to where you go under pressure, and once you can see it, you can stop being run by it. This episode is  learning how the Enneagram works as a map. In this episode, Jen breaks down one of the most misunderstood parts of the Enneagram system: the lines, sometimes called arrows, that connect each type to two others. These lines aren't abstract theory — they show up in real time, in the specific ways you default under stress and the specific ways you can grow beyond your core type. Jen walks through the difference between the high side and low side of a type, what integration and disintegration actually mean, and why understanding this gives you an early warning system for your own patterns. This first installment covers the framework itself, plus a deep dive into how the lines operate for the three heart types — two, three, and four. Part two picks up next week with the head and body types. In this episode, we explore: The map, not the box: Why the Enneagram's wings and lines exist to open you up rather than confine you to a single number.High side vs. low side: How to recognize when you're accessing the most integrated version of a type versus its most reactive, stress-driven patterns.Wings as access points: How the two types neighboring your core number can offer easier, more immediate growth opportunities.The heart types under stress: How twos, threes, and fours specifically disintegrate along their lines — and what the high side of the opposite line offers as a way back.The Work of You - Reflective Prompts:  1. What are the low side patterns you notice coming up for you, and what are some alternative pathways to pull you out of that? 2. What might it look like to move to the high side of your alternative line and see how that changes up the stress cycle? Resources | Links: CP Enneagram Lines Diagram Enneagram Type Deep Dive Mini Course- Promo Code: POD2026 (valid through the end of 2026) Download this Free Resource: Discover Your Hidden Layer of Leadership  iEQ9 Enneagram Assessment  The Work of You | Substack  Instagram | The Work of You Website | The Work of You Instagram | Grow Collective Website | Grow Collective Support the show

    Your Enneagram Lines -- What They're Telling You, Part 1 [S2 Ep31]

  4. Aug 5

    Understanding Your Enneagram Subtype [S2 Ep30]

    Send some fan mail Click Here to Support: *If you're able to support this free independently produced podcast it would mean so much to me * You already know your Enneagram type. But do you know why two people with the same type can look nothing alike? The answer is your instinct — the unconscious force running beneath your type that decides what you protect, what you prioritize, and how you show up when things fall apart. This week Jen unpacks the three instincts — self-preservation, social, and sexual (or one-on-one) — and how each one colors your Enneagram type in a completely different shade. She walks through all nine types under each instinct, calling out the "countertypes" where the instinct actually pulls a type's behavior in an unexpected direction. Jen also gets personal, sharing her own subtype and what it's taught her about a lifelong pattern she's still working to understand. This episode builds the foundation for everything that comes next in the August Enneagram series, including a future deep dive into all 27 subtypes. In this episode, we explore: The three instincts: What self-preservation, social, and sexual instincts each protect and prioritize, and why they operate like an animalistic survival drive.Counter types: How certain types behave opposite to what you'd expect once a specific instinct takes the lead — like a self-preservation Four who looks upbeat instead of moody.Your instinctual stack: Why understanding your dominant, secondary, and repressed instinct matters, and how overusing one keeps you from your growth edge.Jen's own subtype: What it's been like living as a Type 2 with a dominant sexual instinct, and the personal pattern it's taken her years to understand.The Work of You - Reflective Prompts:  1. Which instinct feels most like home to you? 2. For the next week, try going without one of your comforts/routines or try focusing on someone else's needs or desires over your own and see what that's like. 3. Which of the three instincts perhaps sounds the least like you? Resources | Links: Enneagram Type Deep Dive Mini Course- Promo Code: POD2026 (valid through the end of 2026) Download this Free Resource: Discover Your Hidden Layer of Leadership  iEQ9 Enneagram Assessment  The Work of You | Substack  Instagram | The Work of You Website | The Work of You Instagram | Grow Collective Website | Grow Collective Support the show

    Understanding Your Enneagram Subtype [S2 Ep30]

  5. Jul 29

    Enneagram 101 -- Why It's Your Leadership Superpower [S2 Ep29]

    Send some fan mail Click Here to Support: *If you're able to support this free independently produced podcast it would mean so much to me * Most personality tools tell you what you do. The Enneagram tells you why — and that's where real leadership work begins. If you've heard the word thrown around but never quite understood what makes it different, or if you've taken the assessment and wondered what to actually do with your results, this episode is your foundation. This is the most-downloaded episode in The Work of You catalog, and it's back for good reason: August is going all-in on the Enneagram (including a special new offer), and this is your on-ramp. Jen breaks down what the Enneagram actually is — a nine-point map of core motivation, not behavior — and why that distinction changes everything. She walks through the iceberg model, the three centers of intelligence, and the role of instincts in shaping how your type shows up in the world. Whether you're brand new to the Enneagram or have been sitting with your results without knowing what to do next, this episode gives you the framework to make the information mean something.  In this episode, we explore: What makes the Enneagram different: Why this tool works at the level of subconscious motivation rather than surface behavior — and why that depth is exactly what leadership development requires.The three centers of intelligence: How the body, heart, and head centers organize the nine types, what each center cares about most, and how knowing this becomes a practical cheat sheet for understanding yourself and the people you work with.Instincts and subtypes: What the three instincts are, how your dominant instinct colors the way your core type shows up, and why this layer of data matters as much as your type number.The Work of You - Reflective Prompts:  1. When you consider how you experience the world and take in information, what feels most important to you? Having certainty and safety, being in connection, and feeling seen and valued, or being in control of your environment? 2. What might be your go-to strategy to ensure this in your life? To ensure feeling safe, feeling seen, or being in control.  3. What patterns or ways of being or ways of acting does this bring out in you? What do you notice for how you're showing up at home, at work, or with your team? Resources | Links: [S1 E5] Why the Enneagram is a Leadership Superpower Download this Free Resource: Discover Your Hidden Layer of Leadership  iEQ9 Enneagram Assessment  The Work of You | Substack  Instagram | The Work of You Website | The Work of You Instagram | Grow Collective Website | Grow Collective Support the show

    Enneagram 101 -- Why It's Your Leadership Superpower [S2 Ep29]

  6. Jul 22

    Living in Alignment at 50! [S2 Ep28]

    Send some fan mail Click Here to Support: *If you're able to support this free independently produced podcast it would mean so much to me * Turning 50 has a way of making you honest. On the eve of her fifth decade, Jen pulls up the very first episode she ever recorded — Living in Alignment: The First Step to Leading You — and asks herself the question she asks everyone else: am I actually living this? The answer is yes. And the story of how she got there is worth hearing again, whether for the first time or the tenth. This episode pairs a birthday reflection with a replay of Jen's inaugural episode, built around a simple but powerful framework she sketched in a notebook during coach training at the Hudson Institute. Using a visual of six arrows — career, community, family, friends, love, and current job — she maps what it looks like to spend your twenties and thirties pointing yourself toward everything outside you, and what it takes to finally flip those arrows back in. Jen walks through her own five-year reckoning: leaving Philadelphia, losing her mom, launching a coaching practice from scratch, and landing in Austin with every arrow pointing inward. She closes the episode with concrete prompts to help you do the same inventory on your own life. In this episode, we explore: The alignment framework: A visual tool Jen developed in coach training — six arrows, one for each major life system — that reveals where you're living authentically and where you're still trying to fit yourself to something outside you.The shock point moment: How losing her mom at 33 became the pivotal event that reshaped every aspect of Jen's life — geography, career, relationships, and sense of self — and introduced her to the concept of Post-Traumatic Growth.Flipping the arrows: A year-by-year account of how Jen changed her city, career, friend group, and more — and why it was the hardest, most rewarding work she's ever done.The Work of You - Reflective Prompt:  1. Where am I living in alignment and where may I be out of alignment? Resources | Links: 50 Layers Deep (Jen's birthday essay) — available on The Work of You Substack this week Living in Alignment - The First Step in Leading You [S1 E1] Download this Free Resource: Discover Your Hidden Layer of Leadership  Instagram | The Work of You Website | The Work of You Instagram | Grow Collective Website | Grow Collective Support the show

    Living in Alignment at 50! [S2 Ep28]

  7. Jul 15

    Summer Reflection - What Chapter Are You In? [S2 Ep27]

    Send some fan mail Click Here to Support: *If you're able to support this free independently produced podcast it would mean so much to me * We talk a lot about what's next. But before you can get there, you have to know where you actually are. This summer reflection episode revisits one of the most listened-to episodes of Season 1 — a deep dive into the Hudson Institute's Cycle of Renewal — because no matter how many times you hear it, it lands differently depending on which chapter of life you're currently living. Season 1, Episode 17, framed with a personal reflection from Jen as she approaches her 50th birthday and a significant life transition of her own. The episode introduces the Hudson Institute's Cycle of Renewal — a four-phase model for understanding where you are in any major chapter of life or career. Jen walks through each phase (Go for It, the Doldrums, Cocooning, and Getting Ready), what they feel like from the inside, and what they ask of you. Whether you're mid-stride, stuck, healing, or quietly preparing for something new, this framework gives you language for what's already happening. In this episode, we explore: The Cycle of Renewal: A breakdown of the Hudson Institute's four-phase model and how to identify which phase you're currently in across life, career, or relationship.Mini transitions vs. transformation: Why swapping jobs or changing your circumstances can work for a while — and what it means when it stops being enough.Being vs. doing: How the energy shifts between phases, and why slowing down in the right-side phases isn't stalling — it's the work.Coaching through the cycle: How this framework helps leaders meet others (and themselves) where they actually are, rather than where they think they should be.The Work of You - Reflective Prompts:  1. What if we thought about our life in chapters?  2. How might that guide you differently for assessing where you are in life and how might it ready you for what possibly could be the next chapter? Resources | Links: [S1 E17] Exploring Your Life Chapters Download this Free Resource: Discover Your Hidden Layer of Leadership  Hudson | The Cycle of Renewal  Hudson | Life Forward Retreat The Work of You on Substack Instagram | The Work of You Website | The Work of You Instagram | Grow Collective Website | Grow Collective Support the show

    Summer Reflection - What Chapter Are You In? [S2 Ep27]

  8. Jul 8

    A Takeaway -- Wisdom From Every Season 2 Guest [S2 Ep26]

    Send some fan mail Click Here to Support: *If you're able to support this free independently produced podcast it would mean so much to me * Season two brought some of the most honest, grounded voices Jen has had on this show — coaches, leaders, doctors, and creatives who are all doing their own inner work. This episode is a collection of what they left behind: the practices, prompts, and hard-won wisdom they'd hand you if they had one more minute with you. Consider it a resource you return to, not just something you listen to once. Jen compiles the most actionable takeaways from every season two guest — not a highlight reel, but a practical guide to what each person would want you to actually do after listening. From Eileen Joyce's defining moments timeline to Damon's Sunday planning ritual, each guest offers one concrete practice for doing the work of you. The episode covers self-awareness tools, body-centered practices, creative expression, accountability systems, and the courage it takes to grow with support rather than alone. Think of it as a menu: not everything all at once, but something here is meant for you right now. In this episode, we explore: Mapping your defining moments: Eileen Joyce's practice of plotting milestone moments on a timeline — and why the small, courageous ones matter just as much as the big ones.The body, health, and self-compassion: Heidi  Jones and Dr. Anna Teerlink on keeping physical health simple, and on reframing mistakes as lessons rather than failures.Creative expression as inner work: Nikki Schultz and Brannan on why art, writing, and any form of making opens the heart and accelerates growth in ways productivity tactics can't.Structure, accountability, and support: Damon's Sunday time-blocking practice and Diane Ring's reminder that real growth rarely happens in an echo chamber.The Work of You - Reflective Prompts:  1. Eileen Joyce: Draw a line horizontally to show your life so far and ask yourself, what is one of those defining moments and plot it on the timeline.  2. Kat Gordon: Look at what you're capable of and ask yourself, what else is possible for me? 3. Tony Ross: What is one thing that you can do this summer that feels totally new, and stretches yourself? 4. KG Treser: Come up with a mantra or focus that can help you to reground and be a touch point to refer back to. 5. Brannan Sirratt: What is one way this summer that you can show up fully as yourself and for ourself? Resources | Links: Download this Free Resource: Discover Your Hidden Layer of Leadership  Who You Become When You Stay in the Work -- with My Coach, Eileen Joyce [S2 Ep1]  No One Is Coming to Save You — with Damon D’Amore [S2 Ep3] Taking The Rocks Out of the Backpack -- with Kat Gordon [S2 Ep 4] The Work of Holding Both - Interview with Nikki Shultz [S2 Ep 7] Climbing What's in Front of You-- Interview with Tony Ross [S2 Ep9] Being Strategic in Leading You – Interview with KG Treser, LinkedIn [S2 Ep10] Consistency Over Complication -- with Heidi Jones [S2 Ep13] The Work of Showing Up — with Brannan Sirratt [S2 Ep14] The Real Work of Self Care - with Dr Anna Teerlinck [S2 Ep16] The Advice You Give vs. The Life You Live -- with CCO Jason Sperling [S2 Ep 18] The Gift Hidden Inside Your Enneagram Type — with Diane Ring [S2 Ep 20] What Happens When You Stop Doing Life in Order — with CPO Keesha Jean-Baptiste [S2 Ep 21] EQ Is Not a Soft Skill — with Juan Cortés [S2 Ep 22] The Work of You on Substack Instagram | The Work of You Website | The Work of You Instagram | Grow Collective Website | Grow Collective Support the show

    A Takeaway -- Wisdom From Every Season 2 Guest [S2 Ep26]
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About

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.

Information

  • Creator
    Jen Ostrich
  • Years Active
    2025 - 2026
  • Episodes
    68
  • Rating
    Clean
  • Copyright
    © 2026 The Work of You
  • Show Website
    The Work of You

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