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. Being Strategic in Leading You – Interview with KG Treser, LinkedIn [S2 Ep10]

    2D AGO

    Being Strategic in Leading You – Interview with KG Treser, LinkedIn [S2 Ep10]

    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 week's episode, Jen has an open conversation with KG Treser, a Chief of Staff at LinkedIn, who is on a mission to democratize executive-level skills for everyone. We dive into the gritty reality of the “gear shift” required to move from being a high-performing doer to a strategic leader who leads with a point of view—even when you feel like you’re just making it up. KG opens up about her own “Swiss Army Knife” of inner work, exploring how everything from tarot cards to spot patterns to using AI for processing helps her navigate the high-pressure world of tech with authenticity and grace. In this episode, we explore: The pivotal "gear shift" from operator to strategistBreaking down strategy: goals, constraints, and the blend of IQ and EQUsing "clean systems" like the Enneagram and Tarot to identify blind spotsThe "Enneagram 2 Shadow" and the power of shifting worldviewsHow to use AI (Claude and Copilot) to navigate complex team dynamicsGrounding yourself in simple mantras to rewire core beliefsThe Work of You Resource- via KG Treser Come up with a simple and concise mantra to help you focus  and reground About the Guest:  KG is a Chief of Staff with over a decade of experience in strategy and operations, including nearly seven years at LinkedIn. She's also the creator of Chief of Staff School, a Substack newsletter and TikTok community with over 17,000 followers, where she breaks down strategy frameworks and workplace skills for professionals without an MBA. When she's not supporting senior leaders, she's helping other Chiefs of Staff and future executives level up through her coaching practice. Resources | Links:  Chief of Staff School | KG's Substack TikTok | Follow KG Instagram | Follow KG  The Work of You | Substack GET YOUR ENNEAGRAM TYPE -- includes the Instinct data; most ideal for professional use: leaders and teams ALT OPTION FOR TYPING - also includes the Instincts  The Grow Effect Coaching Model  Instagram | The Work of You Instagram | Grow Collective Website | The Work of You Website | Grow Collective Support the show

    30 min
  2. Climbing What's in Front of You-- Interview with Tony Ross [S2 Ep9]

    MAR 11

    Climbing What's in Front of You-- Interview with Tony Ross [S2 Ep9]

    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.** In this Season Two conversation of The Work of You, Jen sits down with (now retired) executive leader Tony Ross to explore the inner growth behind a 20+ year career at Apple. Tony reflects on the pivotal transitions from individual contributor to manager to leader of leaders, sharing candid lessons on delegation, strategy, culture-building, and leading across global teams. From navigating cultural differences in China to hosting “gelato with Tony” sessions to become more approachable, he offers practical insight into the mindset shifts that elevate good leaders into impactful ones. The conversation also highlights the role of self-awareness and continuous development—both personally and organizationally—including how tools like the Enneagram can strengthen team dynamics. Now in retirement, Tony shares how witnessing his parents’ health journeys inspired him to prioritize adventure and meaning, leading him to climb Denali—twice. His closing message is simple and powerful (see below for his The Work of You advice) -- this is a must watch episode.  In this episode, we explore: Why moving from individual contributor to manager requires a complete mindset overhaul, not just a promotionHow Tony reshaped team norms and built connections at scale to humanize executive leadership Using tools like the Enneagram and intentional development plans to fuel both personal growth and stronger team dynamicsWhat summiting Denali taught Tony about mindset, resilience, and taking bold steps before “someday” slips awayThe Work of You Resources -- via Tony Ross Stay Curious -- question things, take on new challenges, push yourself out of your comfort zone and set concrete goals each yearKeep Growing!About the Guest: With over 20 years of operational leadership at Apple, Tony brings deep expertise in global supply chain, planning, and product operations. He currently advises mission-driven startups like Crowdstake and serves on nonprofit boards focused on health and economic growth. His career began as a Navy engineering officer and continued through senior roles in the tech sector, supported by degrees from Cornell and Stanford GSB. Today Tony is dedicated to mentorship, community engagement, and amplifying organizations that create positive impact. Resources | Links:  Simon Sinek Video  [where one of Tony's favoriate quotes lives] Enneagram for Teams  The Work of You on Substack The Grow Effect Coaching Model  Instagram | The Work of You Instagram | Grow Collective Website | The Work of You Website | Grow Collective Support the show

    31 min
  3. Two Things Can Be True – Your Enneagram Type as a Strategy [S2 E8]

    MAR 4

    Two Things Can Be True – Your Enneagram Type as a Strategy [S2 E8]

    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 of The Work of You, Jen explores the idea that “two things can be true” and how the Enneagram can help us hold tension instead of collapsing into either-or thinking. She discusses how your Enneagram type reflects both strengths and shadow sides—and how awareness of both can expand your leadership and personal growth. Jen reframes your type not as a fixed identity or flaw, but as a strategy developed early in life. She shows how integrating new ways of being—balancing opposites like decisiveness and collaboration, ambition and inclusivity, or high standards and grace—can widen your emotional, behavioral, and relational bandwidth. Whether you’re new to the Enneagram or a seasoned enthusiast, this episode offers practical insights and reflective prompts to notice where your natural tendencies may limit impact and how to cultivate growth. In this episode, we explore: The importance of embracing two truths at onceHow to recognize strengths and shadow sidesUsing the Enneagram to expand capacityIntegrating new ways of being for growthThe Work of You Reflective Prompts: 1. Who are you becoming as you loosen your grip on your strategy/Enneagram type? 2. What is one area that you may be overusing or doubling down on (even if it's a strength)? Where might that be limiting the impact that you're having? 3. What would it look like to integrate yourself towards one of these new ways of being? How can you play around with finding balance between your natural way of being? Resources | Links:  S2 Ep7 | The Work of Holding Both - Interview with Nikki Shultz  Follow The Work of You on Substack   GET YOUR ENNEAGRAM TYPE -- includes the Instinct data; most ideal for professional use: leaders and teams ALT OPTION FOR TYPING - also includes the Instincts  Follow The Work of You on Substack   The Grow Effect Coaching Model  Instagram | The Work of You Instagram | Grow Collective Website | The Work of You Website | Grow Collective Support the show

    25 min
  4. The Work of Holding Both - Interview with Nikki Shultz [S2 Ep 7]

    FEB 25

    The Work of Holding Both - Interview with Nikki Shultz [S2 Ep 7]

    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.** In this personal conversation, Jen speaks with executive coach Nikki Shultz about the transformative power of the Enneagram and the importance of ongoing inner work. A certified teacher with CP Enneagram and former speaker at the International Enneagram Association Global Conference, Nikki shares how the system has shaped her leadership, marriage, and parenting. She emphasizes that real impact comes not from “adding value,” but from embodied presence and balanced growth—integrating head, heart, and body, as well as psychological and spiritual development. Reflecting as a Type Seven, Nikki shares how she once bypassed grief during a corporate layoff by defaulting to positivity, and how years later she allowed herself to fully process that loss. She contrasts this with a recent parenting moment where she stayed grounded and emotionally present with her son’s anger, choosing connection over control—evidence of her shift from living in her head to leading with heart and body. She closes with practical wisdom: question your assumptions (head), engage creativity to access emotion (heart), and invite honest feedback (body). True transformation, she reminds us, requires embracing both psychological and spiritual growth. In this episode, we explore: How lasting impact comes from embodied presence, not over-functioningActively engaging your own psychological and spiritual growth to truly support othersHow growth happens through integrating all three centers of intelligence and holding polarities rather than defaulting to one dominant patternPersonal transformation often requires confronting avoided emotionsThe importance of questioning your assumptions, engaging creativity to access the heart, and seeking honest feedback about how others experience you to support embodied, ongoing developmentAbout the Guest: Nikki Shultz is an executive coach and leadership development consultant working at the intersection of the Enneagram and adult development. She helps leaders see how personality both supports and limits growth, and builds the capacity to widen perspective and hold tension. Nikki is professionally certified with CP Enneagram, has spent over a decade in deep study of the Enneagram, and has been a speaker at the International Enneagram Association Global Conference. Nikki was introduced to The Work of You community through host Jen. They first met when Jen was co-leading a Shift Positive training and stayed in touch, becoming colleagues through Grow Collective, and now good friends through their shared love of the Enneagram. Resources | Links:  Nikki's Website Nikki's LinkedIn  GET YOUR ENNEAGRAM TYPE -- includes the Instinct data; most ideal for professional use: leaders and teams ALT OPTION FOR TYPING - also includes the Instincts  Follow on Substack  The Grow Effect Coaching Model  Instagram | The Work of You Instagram | Grow Collective Support the show

    34 min
  5. A Year of Becoming: Fire Horse Energy [S2 Ep6]

    FEB 18

    A Year of Becoming: Fire Horse Energy [S2 Ep6]

    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.** What if this is the year you lead yourself?  In this solo episode, I explore the powerful overlap between Chinese astrology and numerology as we move from a Year 9 of completion into a Year 1 of beginnings — and from the reflective energy of the Wood Snake into the bold momentum of the Fire Horse. This is about shifting from internal calibration and external expansion.  I share a simple, grounded explanation of both systems and reflect on what it means to close a chapter well — and then consciously step into initiation, identity, and leadership. If last year asked you to release, refine, and shed old skin, this year may be inviting you to move with bold action. We talk about endings, courage, momentum, self-leadership, and what it really means to trust your own fire. If you’ve felt the shift from reflection to readiness… this episode is for you. Episode Topics •A simple explanation of Chinese astrology (animal + element) •What the Wood Snake symbolized and why 2025 was about refinement and release •The themes of a Numerology Year 9: completion, closure, and integration •How Year 9 prepares the ground for what’s next •Entering a Numerology Year 1: initiation, identity, and new beginnings •Fire Horse energy: momentum, visibility, courage, and self-trust •The shadow side of fire (burnout, reactivity, isolation) •Moving from shedding to starting •What it means to lead yourself this year •Reflective questions to help you identify what you’re ready to initiate The Work of You Reflective Prompts:  What is one dream big or small that I've been ignoring for far too long?Where am I ready to take initiative in work or in life?What is one forward step I'm ready to take right now?Resources | Links:  S1 Ep1: Living in Alignment: The First Step to Leading You Substack: The Year of Becoming  The Grow Effect Coaching Model  Instagram | The Work of You Instagram | Grow Collective Website | The Work of You Website | Grow Collective Support the show Support the show

    24 min
  6. From Rescue to Responsibility -- What Two Conversations Revealed [S2 Ep5]

    FEB 11

    From Rescue to Responsibility -- What Two Conversations Revealed [S2 Ep5]

    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 * What happens when you stop waiting and begin choosing to take full responsibility for your life? This Season 2 episode explores the shift from being rescued to stepping into personal authority, and what it looks like to stay in the work without self-abandonment. After two very different conversations—with Damon D’Amore and Kat Gordon—I noticed they were pointing to the same deeper truth from opposite directions: no one can do this work for you, and that realization doesn’t have to be harsh. It can be grounding. Liberating. Clarifying. In this solo episode, I unpack the common threads between two interviews and explore what it actually means to move from waiting into responsibility—without self-abandonment, punishment, or isolation. This is an invitation to notice where you might still be waiting for clarity, permission, or certainty… and what becomes possible when you choose to stay in the work instead. In this episode, we explore: The hidden ways we wait to be rescued as adultsWhy “responsibility” doesn’t have to mean doing everything aloneThe difference between self-reliance and self-abandonmentHow Damon and Kat arrive at the same truth from different pathsInternal authority vs external validationResponsibility as the ability to respond, not a burdenWhat actually changes when you stop waiting and start choosingThe Work of You Reflective Prompts:  Where am I still waiting to be rescued?What responsibility feels ready to be claimed? Where do you feel ready to step into your power of taking responsibility?What would staying in the work look like right now?Resources | Links:  S2 Ep4 - With Kat Gordon S2 - Ep 3 - With Damon D'Amore The Grow Effect Coaching Model  Instagram | The Work of You Instagram | Grow Collective Website | The Work of You Website | Grow Collective Support the show Support the show

    24 min
  7. Taking The Rocks Out of the Backpack -- with Kat Gordon [S2 Ep 4]

    FEB 4

    Taking The Rocks Out of the Backpack -- with Kat Gordon [S2 Ep 4]

    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 Season Two conversation of The Work of You, Jen sits down with her own longtime client turned friend and colleague, Kat Gordon, for an honest exploration of what doing the work of you actually requires. Kat is the founder of the 3% Movement and co-founder of the 3% Coaching Coalition, and this conversation traces her personal evolution from creative leader to coach, Reiki master, and guide for others navigating growth, identity shifts, and leadership from the inside out. Together, Jen and Kat reflect on how coaching works not by fixing us, but by helping us notice the unseen beliefs, patterns, and “rocks in the backpack” we’ve been carrying for years. This episode explores the role of relationship in growth, why self-awareness precedes real change, and how staying with discomfort can unlock clarity, self-trust, and alignment. It’s a grounded, deeply human conversation about leadership, transformation, and learning how to lead yourself with more honesty and compassion. In this episode, we explore: •How Kat’s work with the 3% Movement evolved into the 3% Coaching Coalition •Why coaching became the next natural chapter in her leadership journey •The impact of long-term coaching relationships on personal and professional growth •What “live it to give it” means in coaching, leadership, and inner work •The role of active listening in transformation •How somatic practices like Reiki complement mindset-based coaching •Why journaling (morning pages) can accelerate self-awareness and clarity •The idea of “rocks in the backpack” and how unexamined beliefs weigh us down •Letting go of conditional worth and reclaiming self-trust •How the Enneagram can illuminate both our strengths and blind spots •Why growth isn’t about avoiding discomfort—but learning from it The Work of You Resource -- via Kat Gordon Morning Pages (inspired by Julia Cameron): first thing when you wake up take pen to paper and free forum write your thoughts for 3 pages worth. Bonus: Reflect back after a month or two on what was on your mind in the pervious month. What are you noticing? How are you growing? About the Guest: Kat Gordon is Founder of The 3% Movement and Co-Founder of The 3% Coaching Coalition. As an Executive Coach for Creative Leaders, Kat helps clients be the kind of leaders they wish they had as young creatives. Drawing upon her years as a diversity leader and recent study as a Reiki Master, Kat brings a level of soulfulness and inclusion to her work that help clients access their deepest knowing.  She was named one of "30 Most Creative Women in Advertising" by BusinessInsider and "Visionary of the Year" from Advertising Age.  Resources | Links:  Kat Gordon Substack Kat Gordon Website 3% Coaching Coalition  GET YOUR ENNEAGRAM TYPE -- includes the Instinct data; most ideal for professional use: leaders and teams ALT OPTION FOR TYPING - also includes the Instincts  The Grow Effect Coaching Model  Instagram | The Work of You Instagram | Grow Support the show

    28 min
  8. No One Is Coming to Save You — with Damon D’Amore [S2 Ep3]

    JAN 28

    No One Is Coming to Save You — with Damon D’Amore [S2 Ep3]

    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 Season Two conversation of The Work of You, Jen sits down with longtime mentor, executive advisor, and storyteller Damon D’Amore for an unfiltered look at resilience, responsibility, and what real self-leadership demands. Drawing from four careers, multiple ventures, and decades working with C-suite leaders, Damon shares the lessons that shaped his philosophy: no one is coming to save you, meaning is yours to create, and growth requires daily honesty with yourself. Together, they explore mentorship, negative motivation, long-term discipline, and why doing the work means facing discomfort instead of bypassing it. This episode is a grounded, provocative conversation about inner accountability, surviving hard seasons, and learning how to show up fully — even when the outcome isn’t guaranteed. In this episode, we explore: The mentors who shaped Damon’s career and leadership philosophyWhy “no one is coming to save you” is a call to empowerment, not fearNegative motivation and managing future regretThe role of mentorship in entrepreneurship and leadership growthGiving yourself grace without losing momentumThe “Rocky Test” and being radically honest with yourselfWhy resistance, imposter syndrome, and inner patterns always returnCreating structure, discipline, and accountability that actually worksDefending your time and working in focused seasonsWhy leaders need a clear point of view — and the courage to share itThe Work of You Resources -- via Damon D'Amore 90-day planning and goal alignmentTime blocking and defending creative work timeMonthly self-reviews and accountability systemsStoic principles and emotional regulationAbout the Guest: Damon has spent more than 20 years working directly with C-Suite leaders in Fortune 500 firms. His work focuses on psychological performance, crisis leadership and storytelling to gain stakeholder advocacy. Damon speaks internationally on storytelling, legacy, women in leadership, resilience, mindset, and applying the lessons of entrepreneurship to corporate environments. More than half of Damon’s clients are female leaders in the C-Suite.  Resources | Links:  Damon's Results Over Regrets Substack Damon's Website GET YOUR ENNEAGRAM TYPE -- includes the Instinct data; most ideal for professional use: leaders and teams ALT OPTION FOR TYPING - also includes the Instincts  The Grow Effect Coaching Model  Instagram | The Work of You Instagram | Grow Collective Website | The Work of You Website | Grow Collective Support the show

    33 min
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5
out of 5
22 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
    44
  • Rating
    Explicit
  • Copyright
    © 2026 The Work of You
  • Show Website
    The Work of You

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