Underdog Leadership Podcast

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 ou...

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...

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. Je...

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...

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,...

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 le...

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...

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 pedali...

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...

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...

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 -...

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—espe...

"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. Defin...

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...

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, tr...

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 tha...

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,...

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 the...

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 milesto...

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 metho...

In this episode, Jenny Mitchell and nonprofit expert Dr. Patton McDowell dive into shifts redefining the sector, from evolving financing models to the rise of contract work and organizational mergers. These changes aren't just relevant for nonprofits - they offer lessons for leaders everywhere about adaptability and innovation. A central theme of the episode is women's leadership, where Patton and...

Have you ever found yourself stepping in to protect your team from failure, only to realize that your well-intentioned actions might be holding them back? In this episode of the Underdog Leadership Podcast, host Jenny Mitchell dives deep into the intriguing concept of 'mothering' in the workplace. Discover how many women leaders parallel their career milestones with family stages, leading to prote...

In this episode, Jenny Mitchell takes you behind the scenes of leadership struggles we all face and specifically, her own personal battle with self-sabotage. She shares 7 powerful strategies to stop undermining yourself and step into your leadership potential. A recent coaching call with a promising young leader inspired this episode, where Jenny explores the subtle yet significant behaviors that...

In this episode, Dave Hutchinson and Jenny Mitchell dive into the talent crisis shaking up the non-profit world, especially in Canada. With boomers retiring and Gen X mysteriously under-engaged, who's going to step up? Their answer: millennials in their mid-30s to early 40s! But it's not just about filling seats - organizations need thoughtful, values-driven succession planning to secure the right...

The Underdog Leadership Podcast is BACK with Season 5! In this eye-opening first episode of Season 5, host Jenny Mitchell sits down with Christina J. Schoemaker, MBA, CFRE, Senior Vice President for Advancement at Valley Youth House. Get inspired by Christina's journey from health care to leading the development team at a local youth-focused nonprofit. Over 10 years, Christina transformed her depa...