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

Dr. Benjamin Ritter, Live for Yourself Consulting

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

Fearless Friday: Clarify Expectations

Dr. Benjamin Ritter, Live for Yourself Consulting

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.

Fearless Friday: Never Have Too Much Work

Dr. Benjamin Ritter, Live for Yourself Consulting

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.

Fearless Friday: Avoid Burning Out

Dr. Benjamin Ritter, Live for Yourself Consulting

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.

Fearless Friday: Accept the True Meaning of Work

Dr. Benjamin Ritter, Live for Yourself Consulting

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.

Discomfort Is Where the Value Is with Adam Callinan

Dr. Benjamin Ritter, Live for Yourself Consulting

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

Fearless Friday: Remember How Great You Are

Dr. Benjamin Ritter, Live for Yourself Consulting

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.

Fearless Friday: Do What You Want To Do

Dr. Benjamin Ritter, Live for Yourself Consulting

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.

Trust Your Strengths (Not the Playbook) with Anya Cheng

Dr. Benjamin Ritter, Live for Yourself Consulting

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: anya@taelor.ai
🏷️ 25% off first month (menswear rental): PODCAST25 (https://taelor.style/pages/membership)
🎁 10% off gift cards: PODCASTGIFT (https://taelor.style/products/menswear-rental-gift-card)

Fearless Friday: Shift From Victim To Creator

Dr. Benjamin Ritter, Live for Yourself Consulting

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.

Fearless Friday: Create Instead of Chase Happiness

Dr. Benjamin Ritter, Live for Yourself Consulting

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 Create Instead of Chase Happiness and explores how fear quietly influences our thoughts, decisions, and actions.

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

Trusting Yourself More Than Fear with Meredith “MK” Katz

Dr. Benjamin Ritter, Live for Yourself Consulting

MK is the co-founder of Retrocycle, a Colorado nonprofit building a borrow-and-return network for reusable cups, starting with the Colorado Cup launching in May 2026 in Breckenridge.

In this conversation, we get into what it looks like to lead yourself first while building something uncertain: nervous system regulation, staying steady through emotional waves, and using fear as a signal instead of a stop sign.

MK also shares her path from Zappos and marketing into a full reset (WWOOFing, herbalism, sustainability exploration), how a reuse system in Germany sparked the Retrocycle vision, and why the model is built to last beyond the founders through nonprofit governance, community partners, local government collaboration, and local art on every cup.

If you’ve been craving work that feels real again, this one is a blueprint for choosing trust over fear and building a mission with momentum.

Connect with Meredith “MK” Katz & Retrocycle:

🌐 Retrocycle: https://retrocycle.org/
📸 Instagram: https://www.instagram.com/retrocycle.us/
💼 Meredith “MK” Katz on LinkedIn: https://www.linkedin.com/in/meredithekatz/

Fearless Friday: Share Your Success

Dr. Benjamin Ritter, Live for Yourself Consulting

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 Share Your Success and explores how fear quietly influences our thoughts, decisions, and actions.

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.

From a Poker Table to a Cancer-Detecting Startup with Scott Hickle

Dr. Benjamin Ritter, Live for Yourself Consulting

In this episode of The Live Fearlessly Podcast, Dr. Benjamin Ritter sits down with Scott Hickle, co-founder of Throne, to explore the journey from an unconventional idea to building a mission-driven company focused on improving gut health and enabling earlier cancer detection.

Scott shares insights on:

• Navigating the emotional highs and lows of fundraising

• The realities of solo founding and rebuilding after failure

• Developing the mindset required to pursue ambitious ideas

• Why entrepreneurship is ultimately a process of personal transformation

This conversation offers a candid look at what it takes to build something meaningful—and the growth required along the way.

🌐Learn more about Throne: https://thronescience.com

💼Connect with Scott Hickle: https://www.linkedin.com/in/scotthickle

Explore coaching and resources:
https://liveforyourselfconsulting.com

Fearless Friday: Believe in Yourself

Dr. Benjamin Ritter, Live for Yourself Consulting

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 Believe in Yourself.

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.

From Burnout to Courage with Owen Reader

Dr. Benjamin Ritter, Live for Yourself Consulting

From Burnout to Courage

Rebuilding after losing everything

 What happens when the drive that built your career is the same force that nearly breaks your life?

 In this episode, I sit down with Owen Reader, founder of Indelible, to talk about burnout, bankruptcy, identity collapse, and what it really takes to rebuild when everything falls apart.

 Owen shares how chasing impact and legacy led to exhaustion and disruption — and how hitting bottom forced a complete reset. We explore the uncomfortable truth about fear, why most of what we’re afraid of never materializes, and how courage isn’t a personality trait — it’s a practice.

 In this conversation, we unpack:

•  What burnout actually reveals about your priorities

• How to rebuild after financial and relational collapse

• Why fear can become a compass, not a stop sign

• The discipline of taking one step forward when hope feels thin

• How to live “all in” instead of circling the life you want

If you’re a leader at a crossroads, quietly questioning your direction, or rebuilding after a setback, this episode will resonate.

You’re not alone in the collapse.

And you’re not stuck there either.

Connect with Owen & Indelible:

🌐 Indelible: https://indelible.co

🎙️ The Gathering Business Festival: https://thegatheringfestival.com

💼 Owen Reader on LinkedIn: https://www.linkedin.com/in/owen-reader-611aba24/

Fearless Friday: Don't Believe Your Beliefs

Dr. Benjamin Ritter, Live for Yourself Consulting

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 Feel Your Feelings and explores how fear quietly influences our thoughts, decisions, and actions.

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.

Fearless Friday: Think About Your Thoughts

Dr. Benjamin Ritter, Live for Yourself Consulting

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 Feel Your Feelings and explores how fear quietly influences our thoughts, decisions, and actions.

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.

Fearless Friday: Create a Life That Helps You Feel Good

Dr. Benjamin Ritter, Live for Yourself Consulting

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 Create a Life That Helps You Feel Good.

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.

Fearless Fridays: Choose How You Feel

Dr. Benjamin Ritter, Live for Yourself Consulting

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 Choose How You Feel.

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.