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Underdog Leadership Podcast

Underdog Leadership Podcast

By: Jenny Mitchell
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About this listen

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 were always meant to be, and expand into your best version of yourself. Because right now, the world needs more underdog leadership.2022 Career Success Economics Management Management & Leadership
Episodes
  • 6.8: UNCUT - What DO You Want?
    Jun 26 2025

    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 firm) reminder: You can't have it all, at least not all at once, and leadership means choosing what you want and accepting what comes with it.

    Listener Reflection:
    What do you really want and what are you willing (and not willing) to do to make it happen? Can you give yourself 10 quiet minutes to name it, write it down, and begin making a plan?


    Listen to Episode 6.8 here: https://chavender.com/underdog-leadership-podcast/stop-pleasing-others-and-start-reclaiming-your-leadership-power/



    ✨Buy the Embracing Ambition Book: https://chavender.com/embracing-ambition-the-book/

    Book a discovery call: https://calendly.com/jennychavender/30min?back=1&month=2022-09

    Lean into Meaningful Conversations with this complimentary 20 minute video all about the tools and techniques for moving conversations forward: https://youtu.be/zv1N_ZsDEAs

    Don't miss an episode by joining my Podcast VIP Email List: https://chavender.activehosted.com/f/27

    Catch me on email: jenny@chavender.com

    Check out my website: chavender.com

    Hop on over to Instagram: @jennychavender

    Let's connect on LinkedIn: Jenny Mitchell, CFRE, CEC, DMA

    "See" me on Youtube: https://www.youtube.com/channel/UC0Q97-c98aPUmfhzlpswfsw

    Show More Show Less
    4 mins
  • 6.8: Stop Pleasing Others and Start Reclaiming Your Leadership Power
    Jun 19 2025

    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 means someone might think a bad thought about us. Let them.

    This episode is a must-listen for recovering (or reluctant) people-pleasers, especially women leaders who are ready to get clear, get intentional, and reclaim their voice. If you've been feeling disconnected from what you want, this episode might just be the sign you've been waiting for.

    Key Takeaways:

    1. People pleasing undermines leadership

    2. Self-awareness is the first step to change

    3. Resentment is a red flag

    4. Effective leadership requires tough choices

    5. Empowered leaders lead from intention

    Chapters:

    00:00 Understanding People Pleasing in Leadership

    02:51 The Impact of People Pleasing on Leadership Effectiveness

    06:12 Reactive vs. Creative Leadership Tendencies

    09:05 Navigating Leadership Decisions and External Perceptions

    11:56 Finding Clarity and Streamlining Leadership

    14:42 Empowering Leadership Through Self-Awareness


    If you loved this episode, you’ll also enjoy:

    • Episode 6.5 - The ONE Thing All Leaders Must Do: https://chavender.com/underdog-leadership-podcast/the-one-thing-all-leaders-must-do/

    • Episode 6.4 - Compassionate Accountability for Leaders (ft. Nate Regier): https://chavender.com/underdog-leadership-podcast/compassionate-accountability-for-leaders/

    • Episode 4.1 - Giving Yourself Permission to Do The Big Thing: https://open.spotify.com/episode/715H358Nm9hgPnhgU5UqPO?si=MIvh8apBTeKLA1zPLeiaoA




    ✨Buy the Embracing Ambition Book: https://chavender.com/embracing-ambition-the-book/

    Book a discovery call: https://calendly.com/jennychavender/30min?back=1&month=2022-09

    Lean into Meaningful Conversations with this complimentary 20 minute video all about the tools and techniques for moving conversations forward: https://youtu.be/zv1N_ZsDEAs

    Don't miss an episode by joining my Podcast VIP Email List: https://chavender.activehosted.com/f/27

    Catch me on email: jenny@chavender.com

    Check out my website: chavender.com

    Hop on over to Instagram: @jennychavender

    Let's connect on LinkedIn: Jenny Mitchell, CFRE, CEC, DMA

    "See" me on Youtube: https://www.youtube.com/channel/UC0Q97-c98aPUmfhzlpswfsw

    Show More Show Less
    21 mins
  • 6.7: UNCUT - A Leadership Fable about a Cat, an Electrical Cord, a Backpack
    Jun 12 2025

    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 that other people are capable—even when it’s hard to watch.

    Listener Reflection:
    Have you ever helped without being asked? What would it have looked like to step back with compassion instead?


    Listen to Episode 6.7 here: https://chavender.com/underdog-leadership-podcast/how-successful-leaders-build-strong-communities-around-themselves/



    ✨Buy the Embracing Ambition Book: https://chavender.com/embracing-ambition-the-book/

    Book a discovery call: https://calendly.com/jennychavender/30min?back=1&month=2022-09

    Lean into Meaningful Conversations with this complimentary 20 minute video all about the tools and techniques for moving conversations forward: https://youtu.be/zv1N_ZsDEAs

    Don't miss an episode by joining my Podcast VIP Email List: https://chavender.activehosted.com/f/27

    Catch me on email: jenny@chavender.com

    Check out my website: chavender.com

    Hop on over to Instagram: @jennychavender

    Let's connect on LinkedIn: Jenny Mitchell, CFRE, CEC, DMA

    "See" me on Youtube: https://www.youtube.com/channel/UC0Q97-c98aPUmfhzlpswfsw

    Show More Show Less
    9 mins
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