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. 4d ago

    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]

  2. 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]

  3. 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]

  4. 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]

  5. Jul 1

    Summer Listening Guide [S2 Ep25]

    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 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 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 Listening Guide [S2 Ep25]

  6. Jun 24

    Audience Q+A [S2 Ep24]

    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 * Life doesn't pause for your consistency goals. New job, a move, grief, a team in chaos, an Enneagram type you can't pin down — and you're still expected to show up and lead. To close out June and celebrate one year of The Work of You, Jen opens the floor to audience questions — no prep, no scripts, just honest answers. She tackles everything from managing through personal upheaval, to leading people for the first time, to why your Enneagram test results keep changing. Throughout, she weaves in callbacks to key episodes from both seasons so you know exactly where to go deeper. Think of it as a guided tour through the core frameworks of this show, filtered through the questions you're actually sitting with. In this episode, we explore: Consistency through disruption: How to identify the one thing worth holding onto when a new job, a move, and grief are all happening at once.First-time people management: Why understanding your own values — and naming them out loud to your team — is one of the most underrated moves a new manager can make.The Enneagram and difference: How the three centers of intelligence (body, heart, head) give you a starting point for working with someone who seems wired completely opposite to you.Tracking inner work: Why growth is usually too subtle to feel in real time — and why writing things down is the most practical way to prove to yourself that it's actually happening.Resources | Links: [S2 Ep16] The Real Work of Self Care - with Dr Anna Teerlinck [S2 Ep13] Consistency Over Complication -- with Heidi Jones  [S2 Ep10] Being Strategic in Leading You – Interview with KG Treser, LinkedIn  [S1 E12] Building Your Leadership Brand [S1 E27] Moving Through the World as an Enneagram Body Type (8,9,1)  [S1 E28] The Emotional Blueprint of the Enneagram Heart Types (2, 3, 4)   [S1 E29] The Inner Patterns of The Enneagram Head Types (5, 6, 7) [S1 Ep14] Moving Your Brain From Threat to Reward State   [S2 Ep15] Why Uncertainty Hits You the Way It Does  Get Your Enneagram Report Here Download this Free Resource: Discover Your Hidden Layer of Leadership  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

    Audience Q+A [S2 Ep24]

  7. Jun 17

    One Year of Doing This Out Loud [S2 Ep 23]

    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 * June 18th marks one full year of The Work of You, and Jen marks it the only way she knows how — with radical honesty. She takes you back to where the podcast began: a business that had slowed, time that needed a purpose, and a calling she couldn't ignore. What she didn't see coming was the perfect storm waiting on the other side of launch week — a psychological Enneagram retreat that surfaced repressed trauma, the onset of perimenopause, and months of feeling like a shell of herself. She shares how she navigated all of it, why she kept showing up, and what this year has clarified about what's coming next for The Work of You as a platform. In this episode, we explore: Why the podcast started: How a season of financial uncertainty and slowed client work became the opening for something Jen had been called to build all along.The harder story: What really happened in the second half of 2025 — a psychological retreat that surfaced repressed trauma, perimenopause, and the weekly work of showing up anyway.What commitment actually looks like: The difference between staying accountable to numbers and staying accountable to yourself and the people you're showing up for.What's next: Jen's expanded vision for The Work of You as a full platform — including the Enneagram masterclass, self-guided coaching products, and what's coming in season three.The Work of You - Reflective Prompts:  Where in your life are you showing up even when it's hard, and have you given yourself credit for that?What are you currently doing more for external proof than for internal alignment, and what would it look like to shift that?Is there a version of the next chapter of your life that you're not letting yourself fully imagine yet — and what's in the way?Next Week: Have you had a favorite podcast interview, but wished you could ask the guest for clarification on something? Are you new to the enneagram and have questions on how to understand how it can work as a map? Are you in a leadership position and struggling to figure how to strengthen your relationship with your team? In next week's episode, Jen will be answering your questions on The Work of You Podcast. Submit any and all questions you may have related to the enneagram, leadership, personal growth, or The Work of You here! Resources | Links: Submit Your Question For My Q&A Episode Here LAST CHANCE: Sign Up for The Work of You MasterClass on 6/25 Download this Free Resource: Discover Your Hidden Layer of Leadership  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

    One Year of Doing This Out Loud [S2 Ep 23]

  8. Jun 10

    EQ Is Not a Soft Skill — with Juan Cortés [S2 Ep 22]

    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 * Best intentions don't protect you from blind spots — and Juan Cortés has the mansplaining story to prove it. Juan has spent his career helping organizations build cultures rooted in emotional intelligence, and the most powerful thing he brings to that work is a willingness to turn the lens on himself first.  Juan Cortés, co-founder of Matter of Culture, has led L&D, OD, and DEI inside organizations across advertising, hospitality, biotech, and fintech (to name a few)— and going external gave him something he couldn't get from the inside: clarity. In this conversation, Juan and Jen dig into what it actually means to confuse proximity for influence, why EQ keeps getting dismissed as a soft skill, and what it costs leaders when it does. Juan shares his three R's framework — reflect, repair, recalibrate — and breaks down the four components of emotional intelligence in a way that makes them immediately actionable. This is the episode for anyone who knows they want to show up better but hasn't found the model that makes it click. In this episode, we explore: Inside vs. outside perspective: How going external helped Juan see the gap between what organizations say they want to be and how their people actually feel — and why that gap is almost always a surprise.The three R's: Juan's personal framework for turning self-awareness into action — reflect on what happened, repair by owning it, and recalibrate for what comes next.EQ as the linchpin: Why emotional intelligence isn't a soft skill add-on but the foundation that makes every other leadership skill work — and what gets lost when organizations treat it as optional.Catching yourself in the moment: The story of Juan realizing mid-sentence that he was mansplaining — and why naming it out loud in the room was the whole point.The Work of You via Juan Cortés Self Awareness: What are the things that move me and motivate me? How am I coming across to others? Self Management: How do I prevent myself from reacting and focus more on responding?Social Awareness: What does this person/group/team need from me?Relationship Management: How do I put all of this to play? How might I be coming across to others and what am I doing about it?About the Guest:  Juan Cortés has spent his career helping organizations across the globe build cultures that promote employee development and engagement. With EQ as the linchpin of all development efforts, Juan delivers inclusive learning experiences designed to grow the skills, knowledge and attitudes necessary to succeed as a distributed workforce. Prior to co-founding Matter of Culture, Juan led L&D, OD and DEI efforts for many organizations in industries including advertising, digital marketing, hospitality, biotech, fintech, media, entertainment, retail and publishing. Juan holds professional certifications in training, facilitation and executive coaching. He is also a qualified coach on Myers-Briggs Type Indicator (MBTI). Juan co-chairs the DEIB committee for Hamlin Robinson School in Seattle, Washington.  Resources | Links: Sign up for The Work of You MasterClass on 6/25 Download this Free Resource: Discover Your Hidden Layer of Leadership  Juan Cortés | Linkedin Matter of Culture Emotional Intelligence by Daniel Goleman Emotional Intelligence 2.0 by Bradberry & Greaves  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

    EQ Is Not a Soft Skill — with Juan Cortés [S2 Ep 22]
See All (63)

Trailers

5
out of 5
23 Ratings

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
    63
  • Rating
    Explicit
  • Copyright
    © 2026 The Work of You
  • Show Website
    The Work of You