The Stuck(ish) Podcast

Hosted by Olivia Wolf

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May 2025

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About the show

Have you ever felt stuck and thought it was just you? Good news!! Feeling stuck is a normal part of the life and leadership journey. So come along, and we can go together!

Listen to episodes

37 recent

May 20, 2025Episode 3558 min

Guest Ruschell Gladden: Finding Hidden Treasures

I know so many people (myself included) whose lives were made better by the impact of those people gifted with seeing something in someone before they see it themselves. Ms. Ruschell is one of those gifted people, and in this episode, she joins me to talk about finding hidden treasures, and leading people to elevate their impact, and step into their gifts and into their power. Please join us - you won't be disappointed!

April 9, 2025Episode 351 hr 5 min

Stuck(ish) Stories: Rebuilding Life After the Dark Side of Leadership

In this powerful episode of Stuck(ish) Stories, therapist and returning guest Jillian joins me to unpack the dark sides of leadership—specifically in high-control, high-demand environments. While these patterns are often associated with religious spaces, we explore how they also show up in educational, professional, and other hierarchical systems. Jillian and I share parallel stories of surviving toxic leadership, each from our own context, and reflect on the long road of healing, reclaiming autonomy, and rediscovering trust. This conversation is a raw, honest dive into what it means to navigate leadership trauma and come out the other side with your integrity intact.

March 4, 2025Episode 3458 min

Guest Jillian Eichel-Dobray: Normalizing & Moving Through Stuck

Since the start of this show, I've wanted to have a deeper conversation about being stuck - the time has arrived!! In this episode of The Stuck(ish) Podcast, I sit down with my friend Jillian to explore the deeper functions of feeling stuck—how it presents in our lives, why it happens, and, most importantly, how we move through it. Together, we share personal experiences of being stuck, the hidden roles of grief and upbringing, and the ways connection and community can help us navigate these moments. Whether you're feeling stuck in your career, relationships, or personal growth, this conversation offers insight, reflection, and hope for finding your way forward.

March 3, 20257 min

Stuck(ish) Stories: Introduction

Introducing Stuck(ish) Stories: Tales from the Trenches—a new spin-off from The Stuck(ish) Podcast! In this special series, we're moving beyond leadership to dive into deeper, more personal storytelling and meaningful conversations. We'll explore the messy, beautiful, and raw experiences that shape us, tackling important topics with honesty, curiosity, and heart. This introduction sets the stage for what's to come—stories of resilience, reckoning, and transformation, told by those who've lived them. Stay tuned!!

September 17, 2024Episode 341 hr 1 min

Guest Craig Osborne: Uniquely You and Being One of One

In this episode, I sit down with Craig Osborne, a retired U.S. Army Colonel with 30 years of service and a distinguished career in leadership, education, and sports. Craig uses his expertise in statistics to explore the idea of individuality, challenging the common notion of being "one in a million." His findings reveal that each of us is "one of one"—a truly unique individual. Tune in as we discuss what it means to embrace our uniqueness and how statistics can illuminate this powerful concept.

August 20, 2024Episode 3350 min

Guest Lisa Moody: Inclusion in Education

In this enlightening episode, we welcome Lisa Moody, a visionary special education teacher and my fellow student in the EdD program, who has pioneered a transformative approach to educational inclusion. Lisa shares the inspiring journey behind her hybrid program, which skillfully combines dedicated focus time for special education students with their integration into general education classes. This model enhances learning opportunities for all students and fosters a more inclusive and understanding school environment. Join us as Lisa delves into the challenges, triumphs, and profound impacts of her work on students, educators, and communities alike, underscoring the crucial role of inclusion in shaping a more integrated world.

July 23, 2024Episode 3259 min

Guest Rachel Cushing: Overcoming Imposter Phenomenon

Join us on this enlightening episode as we dive deep into the complexities of the Imposter Phenomenon with Rachel Cushing, a fellow doctoral candidate in the Interdisciplinary Leadership Studies program at Creighton University. Rachel brings her expertise and insights from her 5-minute master class topic, exploring the psychological patterns that contribute to feelings of fraudulence and self-doubt that so many leaders experience. Whether you're a seasoned executive or a budding entrepreneur, this discussion will provide valuable strategies to recognize, confront, and overcome the imposter syndrome. Tune in to discover how you can build a more confident and empowered leadership identity.

May 14, 2024Episode 3046 min

Guest Seth Kleinwort: The Power of TTRPGs

In this episode, we sit down with Seth Kleinwort, Career Advisor at Creighton University and one of Olivia's fellow EdD cohort members, to explore the transformative power of Tabletop Role Playing Games (TTRPGs). Seth shares his passion for TTRPGs and discusses how they go beyond entertainment, offering valuable lessons in social interactions, interpersonal skills, innovation, creativity, and adaptationn. Join us as we uncover the unique opportunities for curiosity and personal growth that TTRPGs provide. Tune in for an enlightening conversation filled with enthusiasm and insight!

May 9, 2024Episode 294 min

Turning the Page: Updates and What's Next

Join me as I share some exciting personal updates, including my recent venture into a doctoral program at Creighton University. Plus, get a sneak peek into future episodes where I'll introduce you to my inspiring cohort members, each with their unique insights into leadership.

February 13, 2024Episode 2848 min

Guest Candace Pomales: Bravery and Dream Chasing

In this inspiring episode, we sit down with Candace, a dreamer who turned her vision into reality by opening her very own coffee shop in Jacksonville, FL, after a bold move from Anchorage, AK. Candace shares the essence of taking risks, embracing courage, and relentlessly pursuing dreams. We delve into her transformative journey, discussing the pivotal moments of bravery, the challenges she faced, and the invaluable lessons learned along the way. Whether it's the art of adapting to new environments, navigating the complexities of entrepreneurship, or fostering community connections, Candace's story is a testament to the power of following one's passion with resilience. Join us as we explore the highs and lows of chasing dreams and discover the insights Candace has gained from her adventure in leadership and personal growth. This episode is a must-listen for anyone looking to be inspired to take that leap of faith toward their own aspirations.