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

    5d ago

    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

    33 min
  2. Summer Listening Guide [S2 Ep25]

    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

    30 min
  3. Audience Q+A [S2 Ep24]

    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

    34 min
  4. One Year of Doing This Out Loud [S2 Ep 23]

    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

    28 min
  5. EQ Is Not a Soft Skill — with Juan Cortés [S2 Ep 22]

    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

    32 min
  6. What Happens When You Stop Doing Life in Order — with CPO Keesha Jean-Baptiste [S2 Ep 21]

    Jun 3

    What Happens When You Stop Doing Life in Order — with CPO Keesha Jean-Baptiste [S2 Ep 21]

    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 episode, Jen is joined by Keesha Jean-Baptiste, a distinguished Chief People Officer specializing in HR transformation, to discuss the courage it takes to lead from your authentic essence when the environment around you is designed to diminish it. Keesha shares her powerful journey of navigating high-stakes leadership roles at companies like Hearst Magazines and Wieden + Kennedy, and the pivotal moment in Geneva where she chose her own integrity over a comfortable paycheck. They dive deep into the concept of "doing life in order" and what happens when the checklist of success—the degrees, the titles, the material gains—no longer satiates your soul. Keesha opens up about her personal rebirth at age 50, shifting from a performative stance to reclaiming her identity as a writer, speaker, and teacher. This conversation is especially for any high-achiever who feels the "quiet exhaustion" of leadership and is ready to trade external validation for internal peace and self-knowledge. In this episode, we explore: Leadership as Energy: Why your impact on an organization is determined by the energy you transmit and how you manage your "inner code" under pressure.The Mid-Life Rebirth: Moving past the "manual" of how life is supposed to look to discover your creative essence and rewrite your own story.The Work of You via Keesha Jean-Baptiste: 1. Do one thing this year that makes you uncomfortable, but in a structured way. How does pushing yourself in this way make you feel? When you start to face discomfort, you get so in touch with yourself by pushing to go deeper. 2. Take a moment and write down a decision that you made that you are proud of and a decision you made that you aren't? What can you learn from how you reacted/acted in each of these situations? 3. Ask someone close to you, "What do you see me doing when I'm at my best? What am I doing when I am my most authentic self? About the Guest:  Keesha Jean-Baptiste is a distinguished Chief People Officer specializing in HR transformation. With a nearly three-decades-long career, she has driven organizational and cultural change at renowned companies such as Hearst Magazines, Wieden + Kennedy, and Richemont International. Keesha holds a certification in compassionate leadership and is a coach for the Shift Positive 360® feedback method, further elevating the deep respect held among Chief People Officers. Her insights have been featured extensively in leading trade publications like ADWEEK and numerous podcasts, underscoring her influence and thought leadership on various HR topics. Resources | Links: Sign up for The Work of You MasterClass on 6/25 Download this Free Resource: Discover Your Hidden Layer of Leadership TWOY S1 E1 | Living in Alignment - The First Step in Leading You Keesha's LinkedIn Keesha's Leadership Cert Program 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

    36 min
  7. The Gift Hidden Inside Your Enneagram Type — with Diane Ring [S2 Ep 20]

    May 27

    The Gift Hidden Inside Your Enneagram Type — with Diane Ring [S2 Ep 20]

    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 milestone 50th episode, Jen is joined by her original Enneagram teacher and mentor, Diane Ring, for a full-circle conversation about the deep architecture of inner work. Diane brings three decades of experience coaching senior leaders to the discussion. They examine the Enneagram not just as a categorization tool, but as a "sense-making" GPS that can help accurately locate where someone is and provide a specific growth path to help move the "edges of a proverbial box". The conversation also dives into the "Core Gift" bridge, a framework that helps  distinguish between defensive personality strategies and the deeper "why" for being in the world. From real-world stories on shifting leader intensity to the introduction of EnneaEdge—an AI-supported Enneagram coaching experience designed for the "moments that matter"—this episode is an invitation to get out of your own echo chamber and engage with a professional mirror. In this episode, we explore: The Enneagram as a Leadership GPS: Understanding the framework as a map that points to where you currently are and provides a specific growth path to help you break out of automatic identities. Shifting from Intensity to Grounded Presence: By recognizing an automatic pattern of "intensity," a leader can experiment with "downshifting" to find a calmer, more productive way of engaging with their team.The Distinction Between Personality and Core Gift: While personality is a strategy system for self-protection, your core gift (such as attunement) is what you are uniquely called to give to the world.EnneaEdge | AI-Supported Enneagram Coaching: To solve the problem of "fall off" after leadership workshops, Diane created an AI coach designed to help professionals apply Enneagram insights when they are most likely to succumb to autopilot default patterns.The Work of You via Diane Ring: Find somebody with professional capabilities, a coach, mentor, or peer-support group, that can help you recognize and reflect on your patterns, motivations, and blind spots. The goal is to intentionally step outside your own echo chamber and build self-awareness through guided reflection.About the Guest:  Diane Ring is an executive coach who has been bringing the Enneagram into the real work of leadership for 30 years. Through her company, Ring Results, she helps senior leaders and teams understand the deeper patterns that shape how they communicate, make decisions, handle pressure, and relate to others. Diane is known for making the Enneagram practical, relevant, and deeply useful—helping leaders see not only why they do what they do, but also the core gifts they are here to bring forward. She serves on the faculty of Integrative Enneagram Solutions and has presented several times at global Enneagram conferences. Diane is also the creator of EnneaEdge™, an AI-supported Enneagram coaching experience designed to help leaders apply insight in the moments that matter. Resources | Links: Download this Free Resource: Discover Your Hidden Layer of Leadership Get Your Enneagram Report Here Diane's Company | Ring Results LinkedIn | Diane Ring 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

    44 min
  8. Permission to Own What You Want [S2 Ep19]

    May 20

    Permission to Own What You Want [S2 Ep19]

    Send some fan mail Click Here to Support: **If you're able and willing to support this free independently produced podcast it would mean so much to me * In this episode, Jen shares a vulnerable personal moment of "standing in her personal power" by handing her book proposal to a New York Times bestselling author—an act that required overcoming her own inner code of playing it small. She explores the "cost of silence" and why declaring a vision is not a jinx, but rather a way to recruit the support and accountability needed to turn ideas into realized reality. Whether you are a high-achiever hiding a dream until success is guaranteed or a perfectionist waiting for the right moment, this conversation is for you. Jen breaks down how different Enneagram types uniquely self-sabotage by keeping their goals invisible and offers practical prompts to help you name your "meaty goals" loudly and proudly. This episode is for any leader ready to stop "building in the background" and start inviting others to walk alongside them in the work of you. In this episode, we explore: Declaring vs. Jinxing: Declaring a goal doesn't jinx it; it recruits others onto your "sidelines" to act as cheerleaders, coaches, or accountability buddies.The Power of "Naming It": Growth comes to those who learn to say the thing out loud—whether it is an observation, a vision, or a dream—even when it feels risky.Listening to the "Tiny Voice": Identifying the instinctual visions that have become difficult to ignore and moving them from your head onto paper.The Work of You - Reflective Prompts:  I would encourage you to sit down for 30 minutes and journal with a couple of these prompts, feel free to come back to them and reflect as needed. 1. What's one thing you've been working on quietly in the background, maybe just in your head, maybe you haven't even written it down yet? What would change if you said it out loud this week? 2. What is something that makes you a little uncomfortable to even think about, but also feels so instinctually on point that it's really become difficult to ignore?  3. Once you've identified a few examples, just name it. You could give it a code name or just write it out in terms of a goal. See what happens once you allowed yourself to lean into this vision or allowed yourself to actually want this for yourself. Resources | Links: Download this Free Resource: Discover Your Hidden Layer of Leadership Sign Up for The Work of You MasterClass on 5/27 Dogs, Boys, and Other Things I've Cried About by Isabel Klee 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

    25 min
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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
    60
  • Rating
    Explicit
  • Copyright
    © 2026 The Work of You
  • Show Website
    The Work of You

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