Jen Ostrich
The Work of You
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 ultim...
Author
Jen Ostrich
Category
Podcast website
Latest episode
Jul 8, 2026
Where to listen?
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Episodes
A Takeaway -- Wisdom From Every Season 2 Guest [S2 Ep26] 08.07.2026 33:11
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 har...
Summer Listening Guide [S2 Ep25] 01.07.2026 30:23
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 * 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 w...
Audience Q+A [S2 Ep24] 24.06.2026 33:49
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...
One Year of Doing This Out Loud [S2 Ep 23] 17.06.2026 27:38
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 i...
EQ Is Not a Soft Skill — with Juan Cortés [S2 Ep 22] 10.06.2026 31:56
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 th...
What Happens When You Stop Doing Life in Order — with CPO Keesha Jean-Baptiste [S2 Ep 21] 03.06.2026 35:33
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...
The Gift Hidden Inside Your Enneagram Type — with Diane Ring [S2 Ep 20] 27.05.2026 44:26
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 disc...
Permission to Own What You Want [S2 Ep19] 20.05.2026 24:53
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...
The Advice You Give vs. The Life You Live -- with CCO Jason Sperling [S2 Ep 18] 13.05.2026 40:00
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 t...
Your Hidden Layers — What I Learned About Mine [S2 Ep17] 06.05.2026 29:06
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 subconsciou...
The Real Work of Self Care - with Dr Anna Teerlinck [S2 Ep16] 29.04.2026 33:41
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,...
Why Uncertainty Hits You the Way It Does [S2 Ep15] 22.04.2026 26:51
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 * Uncertainty is everywhere—from AI upending industries to the constant noise of a volatile world—and it is easy for your system to feel like it’s under attack. In this solo episode, Jen explores why our brains react to instability with the sa...
The Work of Showing Up — with Brannan Sirratt [S2 Ep14] 15.04.2026 35:55
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 sits down with Brannan Sirratt — book developer, coach, and owner of DevelopYourBook.com — for a conversation that starts with manuscripts and ends somewhere much deeper. Brannan spent two decades helping authors find th...
Consistency Over Complication -- with Heidi Jones [S2 Ep13] 08.04.2026 32:52
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 * How we take care of our bodies is a direct reflection of how we lead ourselves. In this episode, Jen is joined by strength coach and close friend Heidi Jones to discuss why consistency—not complication—is the key to long-term wellness. They discus...
The Enneagram as a Mirror and a Map [S2 Ep12] 01.04.2026 28:34
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 solo episode of The Work of You, Jen returns to one of her favorite topics — the Enneagram — with a fresh frame: the mirror and the map. She breaks down what your Enneagram type actually is (and isn't), how to make sense of your...
The Inner Work of Leadership [S2 Ep11] 25.03.2026 23:48
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 synthesizes core themes from her recent conversations with tech leaders Tony Ross (formerly of Apple) and KG Treser (LinkedIn); two leaders who are actively leading themselves. Jen breaks down four insights...
Being Strategic in Leading You – Interview with KG Treser, LinkedIn [S2 Ep10] 18.03.2026 29:46
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 fr...
Climbing What's in Front of You-- Interview with Tony Ross [S2 Ep9] 11.03.2026 31:11
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 mana...
Two Things Can Be True – Your Enneagram Type as a Strategy [S2 E8] 04.03.2026 25:00
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...
The Work of Holding Both - Interview with Nikki Shultz [S2 Ep 7] 25.02.2026 33:51
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 Enneagra...
A Year of Becoming: Fire Horse Energy [S2 Ep6] 18.02.2026 24:08
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 S...
From Rescue to Responsibility -- What Two Conversations Revealed [S2 Ep5] 11.02.2026 24:17
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 se...
Taking The Rocks Out of the Backpack -- with Kat Gordon [S2 Ep 4] 04.02.2026 28:10
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% Moveme...
No One Is Coming to Save You — with Damon D’Amore [S2 Ep3] 28.01.2026 33:00
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 fou...
Reflections: Who You Become When You Stay in the Work [S2 Ep2] 21.01.2026 29:04
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 reflective solo episode of The Work of You , Jen slows things down to integrate the conversation from Season Two’s opening interview with her longtime coach, Eileen. Rather than focusing on quick takeaways, this episode explores what act...
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