The Work of You

Jen Ostrich
  • 5.0 (22)
  • 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. One Year of Doing This Out Loud [S2 Ep 23]

    2d ago

    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
  2. 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
  3. 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
  4. 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
  5. 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
  6. The Advice You Give vs. The Life You Live -- with CCO Jason Sperling [S2 Ep 18]

    May 13

    The Advice You Give vs. The Life You Live -- with CCO Jason Sperling [S2 Ep 18]

    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 Jason Sperling, Chief Creative Officer at INNOCEAN and author of Creative Directions, to discuss the messy, often terrifying transition from being a "man-child" creative to a responsible leader. They explore the unique architecture of those wired for commercial creativity: the outliers who find themselves suddenly responsible for the careers of others while navigating their own imposter syndrome. Jason shares some of his most vulnerable "growth moments," from a high-stakes DEI mistake at Meta Reality Labs to the "periodic peril" of launching the iPad under Steve Jobs. We dive deep into why "candor is kindness" and how the hardest part of leadership is often managing the unrealistic expectations we set for ourselves versus the realistic ones we must set for our teams.  In this episode, we explore: The Transition from Talent to Leader: Why being great at your craft doesn't automatically make you great at managing people, and the emotional maturity required to bridge that gap.Managing Self-Expectations: Learning to separate the perfectionism you demand of yourself from the standards required to lead a healthy, functioning team.The Work of You via Jason Sperling:  "Self-reflection helps build self awareness.""Continue to push and find areas where you can improve. It's very easy to fall into the things that you're talented in and that come naturally to you, but push on those areas where you feel you're deficient with the hope that when you do it long enough it does start to come natural or feel less uncomfortable."About the Guest: Jason Sperling joined INNOCEAN in February 2023 as the Chief Creative Officer, and has helped transform the global agency’s creative vision and leveled up the work. And for the first time in the agency's history they've been included on Ad Age's A-List. Prior to this he served as Global Executive Creative Director for Meta Reality Labs, overseeing the global marketing for VR, AR and Metaverse. During his career he’s developed iconic work for brands like Apple, Honda, TikTok, Amazon, Disney Pixar and UNICEF Worldwide. His work has put him on several industry best lists, including Adweek’s Top 30 Creative Directors and Campaign’s 40 over 40 Best Digital Creatives. And his commitment to culture recently landed him on AdWeek's list of Architects of Culture list. Jason’s most recent book, Creative Directions: Making the Move from Talent to Leader (HarperCollins Leadership, 2021) provides creative people with the tools to become effective creative leaders.  Resources | Links: Jason's Book | Creative Directions Jason's LinkedIn The Work of You Masterclass Free Download: Discover Your Hidden Layer of Leadership The Work of You on Substack Instagram | The Work of You Website | The Work of You Website | Grow Collective Support the show

    40 min
  7. Your Hidden Layers — What I Learned About Mine [S2 Ep17]

    May 6

    Your Hidden Layers — What I Learned About Mine [S2 Ep17]

    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 * Leadership training often fails because it stays above the waterline, coaching the 10–20% of ourselves that is visible while ignoring the vast architecture running beneath. In this solo episode, Jen explores the Hidden Layer: the subconscious "inner code" of beliefs and core fears that act as the true drivers for how you show up. Using the human iceberg model, she shares why behaviors are usually just symptoms and how sustainable change requires working with the layers sitting deep below the surface. Jen also share a vulnerable letter to her 30-something self—a version of her who used "giving" as a strategy to feel lovable while remaining blind to the patterns that were exhausting her. By mapping Jen's own journey as an Enneagram 2, she shows  how naming your hidden layers creates the distance needed to move from automatic ego reactions back to your authentic essence. In this episode, we explore: The Human Iceberg: Why behaviors are symptoms of the subconscious architecture beneath the waterline.The Hidden Layer: A walkthrough of defense mechanisms, beliefs, motivations, and core fears.Transactional vs. Transformational Change: Why working only at the behavior level leads to temporary shifts.Ego vs. Essence: Shifting from automatic survival patterns to intentional self-leadership.The Work of You - Reflective Prompts:  1. Think of a challenging behavior you've been trying to change—if that behavior is just a symptom, what belief is sitting at the bottom of your iceberg driving it? 2. Where is your "inner code" currently running the show without your awareness? 3. If you could name the core fear your ego is trying to protect today, how would that awareness change your next move? Resources | Links: The Work of You Masterclass Free Download: Discover Your Hidden Layer of Leadership Get Your Enneagram Report Here 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

    29 min
  8. The Real Work of Self Care - with Dr Anna Teerlinck [S2 Ep16]

    Apr 29

    The Real Work of Self Care - with Dr Anna Teerlinck [S2 Ep16]

    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 sits down with Dr. Anna Teerlinck — doctor of physical therapy, strength coach, and owner of Austin-based FemPower Physio — at 37 weeks pregnant and fully in motion. Anna works at the intersection of rehab and performance for women, and she brings the same unflinching honesty to this conversation that she brings to her clinical work. Together, they explore what it looks like to take care of yourself when life is full — not as a luxury, but as a non-negotiable. From the "glass balls vs. rubber balls" framework for managing competing roles, to ADHD and the 90-second rule, to why your physical body isn't a separate track from your inner work, this episode is warm, real, and quietly clarifying. In this episode, we explore: The "glass balls vs. rubber balls" framework — and why knowing the difference changes everythingWhy discipline is more sustainable than motivation when it comes to caring for your bodyHow ADHD shaped Anna's self-awareness and her ability to hold space for hard conversationsThe Work of You via Dr. Anna Teerlinck Anna's closing invitation was simple: stop seeing mistakes as failures.  Is there an area of your life where you've "fallen off the wagon" and been hard on yourself about it? What would grace look like there?What's one small thing you can return to today — not perfectly, just intentionally?About the Guest: Dr. Anna Teerlinck is a Doctor of Physical Therapy, strength and conditioning coach, and weightlifting coach dedicated to helping women build resilient, high-performing bodies. She is the owner of Austin-based pelvic floor PT practice, Fempower Physio, where she blends clinical expertise with performance-focused training to support clients from rehab through return to sport and motherhood. As a wife and mom of two, Anna brings both professional insight and lived experience to her work, which has coincided with and is heavily influenced by her neurodivergence and past history of sexual trauma.  Resources | Links: FemPower Physio — Dr. Anna Teerlinck's Austin-based pelvic floor PT practice FemPower Physio Resources (Birth Prep Course coming soon) Anna's ADHD/Subtypes Book Rec  Anna's ADHD/Relationship Book Rec S2 Ep[13] | Interview with Heidi The Work of You | Substack Website | The Work of You Instagram | The Work of You Support the show

    34 min
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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
    57
  • Rating
    Explicit
  • Copyright
    © 2026 The Work of You
  • Show Website
    The Work of You

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