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PODCAST

Underdog Leadership Podcast

Jenny Mitchell, Executive Coach for Women in Leadership

A podcast to help #2"s become #1"s in life and work. Meet your host, Jenny Mitchell, an executive coach, and professional fundraiser. Jenny believes in the power of the underdog - the person who has overcome hardship, stereotyping, typecasting, or debilitating self-doubt to step into the best version of themselves. Underdogs lead with compassion and kindness. These leaders are hard-wired to make the world a better place for everyone. Join Jenny in this podcast to grow your skills, step into who you

business management

All Episodes

03:43

6.8: UNCUT - What DO You Want?

Underdog Leadership Podcast ·

2025/06/26

In this punchy UNCUT mini-episode, Jenny Mitchell dives into one of the hardest questions many of us avoid: What do you want? Sounds simple, but if you’re someone who identifies as a people-pleaser or is constantly tuned in to what others need, this question might leave you blank. Jenny explores how our desire to keep the peace, avoid discomfort, or live up to unrealistic expectations can cloud our own internal compass. Drawing from her own journey as a leader and coach, she offers a loving (but

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21:03

6.8: Stop Pleasing Others and Start Reclaiming Your...

Underdog Leadership Podcast ·

2025/06/19

Ever feel like you're leading a team, running a household, or juggling it all and still putting everyone else’s needs ahead of your own? In this powerful solo episode, Jenny Mitchell dives headfirst into the messy truth about people-pleasing and how it quietly chips away at your leadership potential. With a mix of personal stories, hard-won insights, and “big girl pants” moments, Jenny challenges us to stop managing everyone else’s emotions and start standing firm in our own decisions, even if it

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09:07

6.7: UNCUT - A Leadership Fable about a Cat, an...

Underdog Leadership Podcast ·

2025/06/12

This episode includes a dog, a cat who runs up a tree and gets stuck, an electrical cord, and a leadership lesson. There’s a backyard rescue mission, a personal realization and a few more interesting plot twists. But the real story? It’s not about the cat. It’s about what happens inside a people-pleaser’s mind when something goes wrong, and the urge to fix, help, and over-function takes over. Jenny explores the discomfort of stepping back, resisting the urge to over-help, and learning to trust

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23:47

6.7: How Successful Leaders Build Strong Communities...

Underdog Leadership Podcast ·

2025/06/05

Ever wonder how “that woman” does it? You know the one—she knows everyone, is in the right room at the right time, and has the perfect connection for what you’re looking for. This week, Jenny Mitchell pulls back the curtain on the not-so-secret, yet rarely talked about, art of building and maintaining a powerful leadership network. In this episode, Jenny shares the real reasons behind why strong leaders aren’t just good at their jobs—they’re connected, curated, and community-driven. Whether you're

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04:59

6.6: UNCUT - From New Leader to Confident Boss: Key...

Underdog Leadership Podcast ·

2025/05/29

In this week’s Uncut episode, Jenny Mitchell takes us back to basics with a quick and practical set of "cue cards" — essential reminders for anyone stepping into leadership for the first time. This episode serves as a companion piece to last week’s conversation with Katie McMillan about navigating the first year as a new executive director and the role coaching can play. Leadership is a marathon, not a sprint. Remember to embrace patience and persistence as key leadership traits. If you’re stepping

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30:10

6.6: Navigating Leadership as a New Executive...

Underdog Leadership Podcast ·

2025/05/22

Stepping into a new leadership role can feel like sailing into uncharted, rocky waters—exciting AND terrifying. Your inner critic is loud, your confidence shaken, and the pressure to lead feels overwhelming. In this episode, Jenny Mitchell chats with Katie McMillan, Executive Director of the Milton District Health Foundation, who shares real, raw lessons from her first year as a newly appointed leader. Katie opens up about the moment she knew it was time to move from a supporting role into

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08:06

6.5: UNCUT - Use This Exercise to Prioritize Your...

Underdog Leadership Podcast ·

2025/05/15

Feeling overwhelmed and pulled in a million directions? Take a load off, and have a listen! This episode is a lifeline to clarity. Jenny shares her go-to brain dump exercise—a powerful, simple practice she uses with clients, teams, even her partner—to cut through chaos and zero in on what really matters. Inspired by a Warren Buffett story about ruthless prioritization, this short session walks you through a process to clear mental clutter, sort your goals, and start taking aligned, strategic

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23:35

6.5: The ONE Thing All Leaders Must Do

Underdog Leadership Podcast ·

2025/05/08

In this solo episode, Jenny Mitchell takes listeners deep into one of the most critical skills every leader must master: the ability to prioritize with clarity and conviction. Drawing inspiration from Gary Keller’s book The One Thing, Jenny explores how simplification is not a sign of weakness, but a strategic power move. She shares personal stories — like the shift from pedaling faster to pedaling smarter — and explains how true leadership begins when we train our attention on high-value tasks,

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06:04

6.4: UNCUT - Owning Your Emotions, Thoughts and...

Underdog Leadership Podcast ·

2025/05/01

This Uncut episode explores a powerful shift in leadership: letting others own their experiences. Building on last week’s chat with Nate and inspired by Mel Robbins’ Let Them, we unpack how women leaders overstep in the name of being helpful, offering unsolicited help that undermines others’ confidence. Nate’s insight around the importance of feeling valuable, capable, and responsible reframes how we support others without taking over. We dig into the importance of owning your own behaviour rather

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35:27

6.4: Compassionate Accountability for Leaders with...

Underdog Leadership Podcast ·

2025/04/24

This episode will challenge everything you thought you knew about conflict, communication, and accountability. In this episode, Jenny Mitchell sits down with Dr. Nate Regier, founder of Next Element Consulting and author of Compassionate Accountability. Together, they dive into the often-misunderstood space between being nice and being firm—revealing that true leadership doesn’t have to sacrifice kindness for results. Through candid stories and practical insights, Jenny and Nate explore how leaders

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07:52

6.3: UNCUT - Sacrificial Living

Underdog Leadership Podcast ·

2025/04/17

In this new UNCUT episode, Jenny Mitchell gets raw about a term that was casually dropped by last week’s guest—sacrificial living—and how it shows up in our everyday work lives, especially for entrepreneurs and corporate folks. She shares: - What sacrificial living looks and feels like - The turning point that made her say, “No more.” - Simple, empowering shifts to reclaim your time and energy - Why it’s time to stop letting your work bucket overflow and start filling your life bucket with

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31:49

6.3: Personal Leadership that Delivers Utter...

Underdog Leadership Podcast ·

2025/04/10

Jen Szpigiel, founder of Becoming Iconic, sits down with Jenny to explore what it truly means to lead with courage, make empowered decisions, and step into your future self—before you are ready. We discuss: ✨ Taking bold leaps, even when the path ahead is uncertain ✨ Making decisions as your future self instead of being held back by past doubts ✨ The role of belief and mindset in success—especially when fear and imposter syndrome creep in ✨ Betting on yourself as the ultimate investment, no matter

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05:24

6.2: UNCUT - The Truth Behind Fake it Till You Make It

Underdog Leadership Podcast ·

2025/04/03

“Fake it till you make it.” Jenny explores how the stories we tell about ourselves shape our confidence, actions, and success. Career specialist Michelle Schaefer joined Jenny last episode and described herself as a career storyteller. Jenny reflected on her own journey: early on, she described Chavender as a small consulting firm—until she realized the word “small” was limiting her mindset. Defining yourself as just a VP or just a small business owner will impact your growth. She shares a striking

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34:58

6.2: How To Make Career Development a 365 Day a Year...

Underdog Leadership Podcast ·

2025/03/27

What if losing your job was the best thing that ever happened to you? That’s exactly what career coach Michelle Schafer discovered when an unexpected job loss led her to her true calling. In this episode, Michelle shares her personal journey—jumping across industries from banking to government to nonprofits—before finally finding her passion in coaching. She reveals how discomfort and uncertainty aren’t just challenges but catalysts for reinvention. We’ll also dive into insights from her book,

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04:02

6.1: UNCUT - How To Do a Weekly Time Audit

Underdog Leadership Podcast ·

2025/03/20

Following last week's episode on workaholism, this week's UNCUT is all about taking stock of your time—before burnout hits. Jenny shares one of her go-to strategies: a time audit. When life feels overwhelming and the balance between work and personal life starts tipping, Jenny takes a step back and examines where her time is truly going. She walks you through her method of reviewing past weeks, tracking how much time she spends coaching, in meetings, volunteering, or at home. The numbers don’t lie,

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23:43

6.1: Work Life Integration: Lessons Learned from a...

Underdog Leadership Podcast ·

2025/03/13

The Underdog Leadership Podcast is BACK for Season 6. In this episode, Jenny Mitchell explores the concept of workaholism and how it has evolved over time. Once worn as a badge of honor, being a "workaholic" is now a term many professionals are actively trying to shed. Jenny shares her journey from an overachiever to a high performer, highlighting the importance of work-life integration rather than balance. Through personal stories, coaching insights, and practical strategies, she provides guidance

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56:13

5.9: How to Balance Personal Leadership Growth with...

Underdog Leadership Podcast ·

2025/01/23

What does it take to lead with impact in the nonprofit world while staying true to your personal growth? In this episode, Jenny Mitchell and Kristi Rivait, co-founder of Scale Collaborative, dive into the relationship between personal leadership and organizational development. Kristi shares her journey from growing up in a small-town to becoming a leader in social enterprise innovation. Together, they explore how nonprofit leaders can embrace ambition, overcome imposter syndrome, and adopt an

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52:34

5.8: Things That Women Do in Interviews That Sabotage...

Underdog Leadership Podcast ·

2025/01/09

In this empowering episode of the Underdog Leadership Podcast, Jenny Mitchell is joined by Allison Fuller to tackle a tough topic: how women sabotage themselves during the job application and interview process. Together, they discuss the common pitfalls women fall into, from discounting their strengths to struggling with imposter syndrome. Alison offers practical advice to help listeners break these habits. Topics on this episode include crafting tailored resumes, navigating ageism, and how body

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33:03

5.7: Jenny's Journey: Career Transitions and how to...

Underdog Leadership Podcast ·

2024/12/12

This episode was inspired by a coaching client. She said “Jenny, I’d love to learn more about your career journey and how you navigated your transitions in your professional life.” In this episode, Jenny Mitchell opens up about her personal journey of growth and leadership, diving into how our personal narratives shape who we are, influence our professional lives, and guide us through key milestones. Of course she talks about the challenges of balancing motherhood with ambition, some of her early

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45:19

5.6: Practicing Kindness as a Leadership Superpower...

Underdog Leadership Podcast ·

2024/11/28

What if better leadership starts with simply liking yourself more? In this episode of The Underdog Leadership Podcast, Jenny Mitchell chats with Alan Questel, a Feldenkrais practitioner, about the transformative power of self-acceptance and kindness. Alan shares how focusing on liking ourselves, rather than striving for self-love, can lead to profound personal growth. Through the Feldenkrais method, which emphasizes the mind-body connection, he reveals how small shifts in awareness can ripple out

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