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  • Bet on Yourself: Family, Identity & Leading Fearlessly with Cathy Carroll

    Bet on Yourself: Family, Identity & Leading Fearlessly with Cathy Carroll
    2026/09/28
    What happens when the business you’re leading is also your family—and the role you’ve built your identity around no longer fits? Cathy Carroll knows that tension firsthand. After a successful corporate career, she stepped into leadership in her father’s family business and quickly discovered that leading a family enterprise requires a very different mix of courage, self-awareness, love, and logic. In this episode of Live Fearlessly, Cathy shares how that experience ultimately forced her to question who she was, walk away from an identity she had deeply invested in, and make the decision to bet on herself. Ben and Cathy explore what makes family business leadership uniquely difficult, why family systems matter, how leaders can balance support with challenge, and what it means to stop letting other people define who you are. They also discuss: • Why family business leadership is fundamentally different from corporate leadership • The tension between love and logic • The loneliness that can come with leading inside a family system • How identity gets tied to career, family, and leadership roles • What it means to “self-author” your life • Why Cathy decided to bet on herself and become a coach • The role of emotional development in becoming a stronger leader • How to balance support and challenge in coaching and leadership • Why family businesses require a systems perspective • Cathy’s work training coaches to specialize in family business Cathy Carroll is the Founder and President of Legacy Onward, an internationally recognized family business leadership coach, speaker, and author of Hug of War: How to Lead a Family Business With Both Love and Logic. She is also an ICF Master Certified Coach (MCC).
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    31 分
  • Fearless Friday: Clarify Expectations

    Fearless Friday: Clarify Expectations
    2026/09/11

    Fear isn’t the problem, how we respond to it is.

    In this Fearless Friday episode, Dr. Benjamin Ritter walks through his book, Becoming Fearless: A Journey from Self-Doubt to Self-Mastery.

    This episode is part of an ongoing Fearless Friday series covering all 65 strategies from the book.

    If this resonates, you can find the full book on Amazon:
    https://amzn.to/3YwGBf1
    or learn more at liveforyourselfconsulting.com

    Don’t rush it. One strategy at a time.
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    5 分
  • Fearless Friday: Never Have Too Much Work

    Fearless Friday: Never Have Too Much Work
    2026/08/28

    Fear isn’t the problem, how we respond to it is.

    In this Fearless Friday episode, Dr. Benjamin Ritter walks through his book, Becoming Fearless: A Journey from Self-Doubt to Self-Mastery.

    This episode is part of an ongoing Fearless Friday series covering all 65 strategies from the book.

    If this resonates, you can find the full book on Amazon:
    https://amzn.to/3YwGBf1
    or learn more at liveforyourselfconsulting.com

    Don’t rush it. One strategy at a time.
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    4 分
  • Fearless Friday: Avoid Burning Out

    Fearless Friday: Avoid Burning Out
    2026/08/14

    Fear isn’t the problem, how we respond to it is.

    In this Fearless Friday episode, Dr. Benjamin Ritter walks through his book, Becoming Fearless: A Journey from Self-Doubt to Self-Mastery.

    This episode is part of an ongoing Fearless Friday series covering all 65 strategies from the book.

    If this resonates, you can find the full book on Amazon:
    https://amzn.to/3YwGBf1
    or learn more at liveforyourselfconsulting.com

    Don’t rush it. One strategy at a time.
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    6 分
  • Fearless Friday: Accept the True Meaning of Work

    Fearless Friday: Accept the True Meaning of Work
    2026/07/31

    Fear isn’t the problem, how we respond to it is.

    In this Fearless Friday episode, Dr. Benjamin Ritter walks through his book, Becoming Fearless: A Journey from Self-Doubt to Self-Mastery.

    This episode is part of an ongoing Fearless Friday series covering all 65 strategies from the book.

    If this resonates, you can find the full book on Amazon:
    https://amzn.to/3YwGBf1
    or learn more at liveforyourselfconsulting.com

    Don’t rush it. One strategy at a time.
    続きを読む 一部表示
    5 分
  • Discomfort Is Where the Value Is with Adam Callinan

    Discomfort Is Where the Value Is with Adam Callinan
    2026/07/27
    Most of us spend real energy making our lives a little more comfortable. Adam Callinan has spent his doing the opposite, on purpose. Adam scaled BottleKeeper to more than $60 million in sales with no outside funding and a team of six, then exited to private equity. But the resume is the smaller story. After a decade living on the beach in Manhattan Beach, he and his wife reassessed what they actually wanted for their kids and moved the family to the Montana backcountry. Today he runs Pentane, helping ecommerce founders stop guessing their way to profitability, and twice a year he leads active-duty special operations soldiers into the wilderness through a nonprofit called Big Sky Bravery. In this conversation with Dr. Benjamin Ritter, Adam makes the case that the value you're looking for usually sits on the other side of discomfort. He explains why he built his businesses around hard constraints instead of outside money, how asking "why" three layers deep uncovers what everyone else accepted without thinking, and why he guards his time so carefully now that saying no has become a skill. He also shares what he has learned from operators who make life-or-death decisions for a living, and why pushing your physical limits resets what "difficult" means everywhere else. This episode is for anyone who senses the default path isn't theirs and wants permission to build something more intentional. Bring a notebook. A few of these ideas are worth keeping. Links: Pentane: https://pentane.com Adam Callinan on LinkedIn: https://www.linkedin.com/in/adammcallinan Big Sky Bravery: https://www.bigskybravery.org
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    33 分
  • Fearless Friday: Remember How Great You Are

    Fearless Friday: Remember How Great You Are
    2026/07/17

    Fear isn’t the problem, how we respond to it is.

    In this Fearless Friday episode, Dr. Benjamin Ritter walks through his book, Becoming Fearless: A Journey from Self-Doubt to Self-Mastery.

    This episode is part of an ongoing Fearless Friday series covering all 65 strategies from the book.

    If this resonates, you can find the full book on Amazon:
    https://amzn.to/3YwGBf1
    or learn more at liveforyourselfconsulting.com

    Don’t rush it. One strategy at a time.
    続きを読む 一部表示
    6 分
  • Fearless Friday: Do What You Want To Do

    Fearless Friday: Do What You Want To Do
    2026/07/03

    Fear isn’t the problem, how we respond to it is.

    In this Fearless Friday episode, Dr. Benjamin Ritter walks through the Becoming Fearless strategy Do What You Want To Do.

    This episode is part of an ongoing Fearless Friday series covering all 65 strategies from the book, Becoming Fearless: A Journey from Self-Doubt to Self-Mastery.

    If this resonates, you can find the full book on Amazon:
    https://amzn.to/3YwGBf1
    or learn more at liveforyourselfconsulting.com

    Don’t rush it. One strategy at a time.
    続きを読む 一部表示
    5 分