Live Fearlessly: Living toward greater health, wealth, and happiness

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).

Learn more about Cathy:

Legacy Onward
https://www.legacyonward.com

Hug of War
https://www.legacyonward.com/hug-of-war

LinkedIn
https://www.linkedin.com/in/cathyacarroll

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.

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.

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.

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.

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

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.

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.

Anya Cheng has had a career most people would call “impossible” on paper: Sears, Target, McDonald’s, eBay, Meta and then the leap into founding her own company. In this conversation, Anya breaks down the real strategy behind those moves (and the mindset shift that changed everything): stop optimizing for “better” and start asking what you actually want.

We talk about playing the long game through community, referrals, and being a genuine connector (including how giving first helped her unlock key investor relationships). Anya also shares the origin story behind Taelor, an AI + human-stylist menswear rental that helps busy men look great without shopping or laundry, plus the surprising realities of fundraising as an immigrant woman founder and how she adapted without losing herself.

If you’re building your next chapter, this one is a reminder to leverage your strengths, stay in motion, and let courage look like your version of action.

Connect with Anya & Taelor:

🌐 Taelor: https://taelor.style
💌 Business partnerships / investors: [email protected]
🏷️ 25% off first month (menswear rental): POCAST25
🎁 10% off gift cards: podcastgift

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 Shift From Victim To Creator.

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.