In this episode of Act Three, I sit down with the brilliant and endlessly thoughtful Rishad Tobaccowala—author, futurist, speaker, and longtime global strategist—to talk about what it really takes to build a vibrant next chapter.

Rishad spent nearly four decades at Publicis Group, eventually becoming Chief Strategist and Chief Growth Officer. But his most interesting work, in many ways, began after he left corporate life and stepped into what he calls his "company of one."

We talk about:

🌟 How to prepare for the emotional side of leaving a big career 🌟 What people forget to plan for when they retire or reinvent 🌟 The four pillars every next chapter needs: identity, community, purpose, and growth 🌟 Why your zone of influence matters more than your zone of control 🌟 How to stay relevant in a world changing at high speed 🌟 The surprising truth about attention, status, and "popularity" at work 🌟 How writing, creating, and teaching shaped his Act Two (and soon, his Act Three) 🌟 The value of staying curious—and why it keeps you young 🌟 What he's building now across books, Substack, podcasting, and The Rethinking Work Show

This is a wise, funny, deeply grounded conversation with someone who has navigated big transitions with remarkable clarity. If you're thinking about your future, your identity, or the next stage of your work and life, this episode will give you a lot to consider.

📘 Books • Restoring the Soul of Business • Rethinking Work

📰 Weekly Thought Letter The Future Does Not Fit Into the Containers of the Past – a widely read newsletter for leaders seeking clarity in a changing world.

🎙 Podcast What's Next? – conversations about the forces shaping the future.

▶️ The Rethinking Work Show: https://rethinkingwork.io

🌐 Website: https://rishadtobaccowala.com

00:00 Welcome 01:00 Rishad on leadership and influence 03:00 The meaning of the Advertising Hall of Fame 06:00 How he planned his transition out of Publicis 10:00 The surprising emotional challenges of retirement 12:00 The four pillars: identity, community, purpose, growth 14:00 What people misunderstand about attention and status 16:00 How COVID reshaped the transition 17:00 Building a Substack and an audience 23:00 Why he never charges for his newsletter 26:00 His creative ecosystem: books, podcast, shows 29:00 Staying curious and "forever young" 31:00 Where to follow Rishad's work

If you're starting to think about your own Act Three—or you're already in it—explore my Third Act Blueprint and other resources at https://goodmorningfreedom.com

Subscribe for more conversations on longevity, identity, purpose, and designing a meaningful next chapter.

In this episode of Act Three, host Cara Gray welcomes Jacynth Bassett, a globally recognized expert in age inclusivity and the founder of 'Ageism is Never in Style.' They discuss Jacynth's journey into the field of age inclusivity, inspired by observing his mother's experience of ageism. The conversation covers the importance of intergenerational relationships, the impact of ageism on different age groups, and Jacynth's groundbreaking work in challenging ageist language in marketing. Jacynth also shares insights into societal perceptions of aging and strategies for integrating age inclusivity in personal and professional settings. Stay tuned for practical advice on fostering age-inclusive environments and learn more about how you can contribute to this transformative movement.

00:00 Introduction to Act Three Podcast

00:24 Meet Jacynth Bassett: Age Inclusivity Expert

01:51 Jacynth's Journey into Age Inclusivity

07:11 The Importance of Intergenerational Relationships

12:26 Challenging Anti-Aging Narratives

23:25 Pillars of Ageism is Never in Style

26:17 How to Get Involved with Ageism is Never in Style

28:58 Conclusion and Sponsor Message

https://www.ageismisneverinstyle.com/

This podcast is sponsored by Good Morning Freedom, my consulting practice. I help executives and professionals plan the non-financial part of their retirement, like how to discover new purpose and how you want to spend your time. I offer a 1:1 third-act blueprint package where we work together to discover some new avenues of exploration for your Act Three. This coaching is completely custom and will provide you with a ton of resources and support as you transition to this new stage of life. For all the details, please go to goodmorningfreedom.com.

Connect with Cara on LinkedIn: https://www.linkedin.com/in/caraliveslife/ or Instagram: https://www.instagram.com/caraliveslife/

How do you take control of your aging journey—before a crisis forces your hand?

In this episode of the Act Three Podcast, I sit down with Allison O'Shea, founder of Openly Aging and author of Openly Aging: The Four Pillars to Keep Control. With over 20 years of experience as an executive director in senior living, Allison has seen firsthand the difference between families who plan ahead and those who wait until it's too late.

Together, we explore Allison's Four Pillars of Aging Well:

Support Systems – building the right mix of family, friends, and professionals

Living Environment – choosing a home or community that supports independence

Social Connection – understanding your recreation style and designing connection that fits you

Supportive Services & Finances – knowing what services cost, what insurance covers, and planning before you need them

This conversation is for anyone thinking about their own independence as they age—or supporting parents who are navigating these decisions.

✨ Watch now to learn how to replace fear with confidence and create an intentional plan for your future.

Chapters 00:00 – Welcome to Act Three Podcast

01:05 – Introducing Allison O'Shea & Openly Aging

02:15 – Why planning ahead matters more than you think

04:50 – Pillar 1: Building the right support system

09:30 – Professional support options (care managers, nurse advocates)

11:20 – Pillar 2: Choosing the right living environment 1

3:40 – Downsizing, 55+ communities & "Golden Girls" housing

16:00 – Pillar 3: Social connection and recreation styles 1

8:45 – Purposeful vs social recreation (and why it matters for aging well)

20:10 – Pillar 4: Supportive services & finances

22:30 – Triggers that signal it's time for change (driving, finances, health)

24:20 – When should these conversations start?

25:45 – How Allison works with individuals and families

27:30 – Aging without shame: reframing independence and control

29:15 – TikTok, education, and shifting the culture of aging

30:20 – Final thoughts & how to connect with Allison

📌 Learn more about Allison's work: https://openlyaging.com

Follow Allison on TikTok: https://www.tiktok.com/@allisonoshea_openlyaging

Follow Allison on Instagram: https://www.instagram.com/openlyaging/

📌 Learn more about my work with Good Morning Freedom: https://goodmorningfreedom.com

👍 If you found this conversation helpful, please like, subscribe, and share it with someone who needs to hear it.

Kristen Cavallo's Third Act: From Global Ad CEO to Design Museum Visionary

How do you reinvent yourself after running a world-class ad agency? 🌍 In this candid Act Three conversation, former MullenLowe Group & The Martin Agency CEO Kristen Cavallo reveals how she swapped Super Bowl spots for museum walls—and why a solo 400-mile Camino de Santiago trek became the catalyst for a brand-new purpose.

▶️ What you'll learn in this episode

0:00 Intro & Cara Gray's mission

1:25 Why Kristen planned her exit three years in advance

5:44 The LinkedIn "informational interview" method that shaped her pivot

10:02 Walking the Camino: breaking a 30-year work habit

18:45 Saying no to politics—and yes to design

24:10 Leading the Branch Museum of Design & Architecture

30:35 Building equity & inclusion into cultural programming

41:10 Advice for CEOs plotting their own "third act"

Key takeaways

Use research skills on yourself—Kristen ran 40+ interviews to test possible futures.

A two-week "habit break" can reset lifelong routines.

Non-profits need marketing minds; your corporate skills translate.

Diverse teams aren't a nice-to-have—they prevent creative blind spots.

Design is everywhere; learning to see it makes life more hopeful.

💡 Enjoyed this?

Follow for monthly episodes on designing a purpose-filled retirement.

Visit https://www.goodmorningfreedom.com/

https://branchmuseum.org/

#KristenCavallo #CareerPivot #CaminoDeSantiago #DesignMuseum #AdvertisingCEO #RetirementPlanning #ThirdAct #CreativeLeadership #WomenInLeadership #ActThreePodcast

In this episode of Act Three with host Cara Gray, we welcome Dr. Karen Falkenberg, a lifelong innovator whose career transitions from chemical engineering to championing human potential through teaching, neuroscience, and strength training. Join us as we explore Karen's inspiring journey—from overcoming a life-altering car accident to launching the online health and fitness coaching company, Tiger's Eye Life, with Ryan MacQueen. Learn how Karen empowers busy professionals to enhance their vitality through strength training, nutrition, and mindset coaching, proving that transformation is possible at any age. For more information, visit Good Morning Freedom, Cara's Third Act Consultancy.

00:00 Introduction and Sponsor Message

00:24 Meet Dr. Karen Falkenberg: A Lifelong Innovator

03:25 Career Transitions and Teaching Passion

06:57 The Move to Atlanta and Pursuing a PhD

09:44 Impact at Emory University and Colorado State

12:33 Life-Altering Accident and Recovery

15:13 Discovering Strength Training

19:52 The Benefits of Strength Training

21:25 How to Get Started with Strength Training

27:09 Nutrition and Mental Health

28:49 Virtual Fitness Community and Programs

34:35 Conclusion and Contact Information

Karen's Website: https://tigerseye.life/

Contact: [email protected]

This podcast is sponsored by Good Morning Freedom, my consulting practice. I help executives and professionals plan the non-financial part of their retirement, like how to discover new purpose and how you want to spend your time. I offer a 1:1 third-act blueprint package where we work together to discover some new avenues of exploration for your Act Three. This coaching is completely custom and will provide you with a ton of resources and support as you transition to this new stage of life. For all the details, please go to goodmorningfreedom.com.

Connect with Cara on LinkedIn: https://www.linkedin.com/in/caraliveslife/ or Instagram: https://www.instagram.com/caraliveslife/

Join 3,000+ professionals reinventing retirement. Subscribe to my weekly newsletter: https://www.goodmorningfreedom.com/subscribe

In this episode of 'Act Three,' host Cara Gray welcomes Ann Medlock, a renowned writer, activist, and founder of the Giraffe Heroes Project. They explore Ann's multifaceted career and her new book 'Breadcrumbs: 18 Clues on the Path to a Meaningful, Exciting Life.' From discussing the pitfalls of the Golden Rule to embracing the risks of life and the importance of meditation, Anne shares her wisdom and experiences. They also delve into the significance of service in retirement and the challenges of balancing kindness, forgiveness, and justice. Tune in to gain insights on how to thoughtfully shape the rest of your life.

00:00 Introduction and Sponsor Message

00:24 Meet Ann Medlock: A Multifaceted Life

02:28 Discussing 'Breadcrumbs': Finding Meaning and Purpose

04:00 The Golden Rule vs. The Platinum Rule

05:47 Embracing Risks and Improvisation

07:29 Life Lessons and Personal Reflections

23:13 The Importance of Service and Community

26:22 Current Projects and Future Plans

28:22 Conclusion and Sponsor Reminder

To purchase Ann's Books or connect with her: https://www.annmedlock.com/

Ann's Social Media:

https://www.facebook.com/ann.medlock https://www.facebook.com/AnnMedlockAuthor

https://www.facebook.com/giraffeheroes

https://www.linkedin.com/in/annmedlock/

This podcast is sponsored by Good Morning Freedom, my consulting practice. I help executives and professionals plan the non-financial part of their retirement, like how to discover new purpose and how you want to spend your time. I offer a 1:1 third-act blueprint package where we work together to discover some new avenues of exploration for your Act Three. This coaching is completely custom and will provide you with a ton of resources and support as you transition to this new stage of life. For all the details, please go to goodmorningfreedom.com.

Connect with Cara on LinkedIn: https://www.linkedin.com/in/caraliveslife/ or Instagram: https://www.instagram.com/caraliveslife/

Join 3,000+ professionals reinventing retirement. Subscribe to my weekly newsletter: https://www.goodmorningfreedom.com/subscribe

In this episode of Act Three, hosted by Cara Gray, we delve into a captivating conversation with Alicia Johnson, a writer and transformation specialist. Alicia discusses her upcoming book, 'Buried Treasure,' which blends memoir and practical guidance for trauma recovery through wonder and self-revelation. She also shares her inspiring journey of returning to the modeling industry with Ford Models, breaking barriers as a mature, curvy model. Join us as Alicia talks about her approach to aging, her work in personal and professional renewal, and her exciting future projects, including her forthcoming novel 'Hudson.' Plus, insights on how to plan and intentionally design your third act of life.

00:00 Introduction and Sponsor Message

00:24 Guest Introduction: Alicia Johnson

02:18 Alicia's Modeling Journey

03:06 The Ford Modeling Agency Story

08:59 Representation and Aging in Fashion

15:29 Alicia's New Home Plans

20:23 Back to the Book: Wonder-Based Trauma Recovery

21:00 Personal Trauma and Lifelong Research

21:33 Synthesizing Research During Covid

23:27 The Role of Play and Imagination in Healing

24:32 The Body Keeps the Score

25:57 Making Friends with Your Brain

29:36 Understanding Personal Trauma

32:37 Transformational Projects and Brand Strategy

38:02 Future Projects and Personal Growth

45:12 Conclusion and Final Thoughts

To purchase Alicia's Books or connect with her: https://www.aliciaellejohnson.com/

Forbes Article: How Mature, Plus-size Models are Creating Their Own Runways https://www.forbes.com/sites/kristenphilipkoski/2025/01/30/how-mature-plus-size-models-are-creating-their-own-runways/

This podcast is sponsored by Good Morning Freedom, my consulting practice. I help executives and professionals plan the non-financial part of their retirement, like how to discover new purpose and how you want to spend your time. I offer a 1:1 third-act blueprint package where we work together to discover some new avenues of exploration for your Act Three. This coaching is completely custom and will provide you with a ton of resources and support as you transition to this new stage of life. For all the details, please go to goodmorningfreedom.com.

Connect with Cara on LinkedIn: https://www.linkedin.com/in/caraliveslife/ or Instagram: https://www.instagram.com/caraliveslife/

In this episode of 'Act Three,' host Cara Gray sits down with John Graham, an author, adventurer, former diplomat, and executive director of the Giraffe Heroes Project. John shares his incredible journey of seeking purpose, from hitchhiking through revolutions to climbing dangerous mountains and serving as a U.S. Foreign Service officer and a peacebuilder with the United Nations. He discusses the transformative power of finding meaning through service and highlights his work with the Giraffe Heroes Project, which inspires people to take courageous actions for the common good. Cara and John discuss the importance of finding purpose at any stage of life and offer insights on how to intentionally design a meaningful third act.

00:00 Introduction and Sponsor Message

00:24 Guest Introduction: John Graham

02:02 Early Adventures and Life Lessons

06:35 Diplomatic Career and Foreign Service

08:17 United Nations and Anti-Apartheid Efforts

18:13 Giraffe Heroes Project: Inspiring Stories

27:10 Finding Purpose in Life

30:28 Conclusion and Final Thoughts

Giraffe Heros Project: https://www.giraffe.org/

John's Website: johngraham.org

Find John on Socials:

https://www.facebook.com/giraffeheroes

https://www.instagram.com/johngraham3440

https://www.linkedin.com/in/johnagraham1/

This podcast is sponsored by Good Morning Freedom, my consulting practice. I help executives and professionals plan the non-financial part of their retirement, like how to discover new purpose and how you want to spend your time. I offer a 1:1 third-act blueprint package where we work together to discover some new avenues of exploration for your Act Three. This coaching is completely custom and will provide you with a ton of resources and support as you transition to this new stage of life. For all the details, please go to goodmorningfreedom.com.

Connect with Cara on LinkedIn: https://www.linkedin.com/in/caraliveslife/ or Instagram: https://www.instagram.com/caraliveslife/

In this episode of Act Three, host Cara Gray welcomes Kevin Newby, a versatile professional with over 25 years of experience in startups, marketing and executive leadership. Kevin discusses his journey from traditional advertising to digital, his experience with startups, and the challenges of corporate transitions and acquisitions. He also shares personal insights from his throat cancer diagnosis and how it influenced his career and led him to executive life coaching. Kevin offers a compelling narrative on self-advocacy, professional growth, and the power of mentorship. This episode provides valuable lessons on navigating life's challenges and finding purpose in transformation.

00:00 Introduction and Sponsor Message

00:23 Meet Kevin Newby: A Creative Problem Solver

01:36 Transitioning to Digital: Early Career Challenges

02:53 Navigating Acquisitions and Corporate Changes

06:20 Founding Kadium: Belief and Hustle

09:18 Joining Havas: A New Role and Challenges

16:33 Personal Struggles and Career Impact

20:27 Facing Financial Fears

20:48 Navigating Cancer Treatments

21:13 Self-Reflection and Realizations

23:32 Post-Cancer Challenges

25:43 Joining the Mankind Project

31:37 Embracing Coaching and New Beginnings

36:28 Ideal Clients and Coaching Philosophy

38:55 Conclusion and Contact Information

You can find Kevin here:

https://www.kevinnewby.coach/

This podcast is sponsored by Good Morning Freedom, my consultancy. I help executives and professionals plan the non-financial part of their retirement, like how to discover new purpose and how you want to spend your time. I offer a 1:1 coaching retirement blueprint package where we work together to discover some new avenues of exploration for your Act Three. This coaching is completely custom and will provide you with a ton of resources and support as you transition to this new stage of life. For all the details, please go to goodmorningfreedom.com/.

Connect with Cara on LinkedIn: https://www.linkedin.com/in/caraliveslife/

In this episode of 'Act Three,' host Cara Gray sits down with Elvi Moore, a distinguished figure in the performing arts world whose career spans over five decades. From her beginnings as an associate professor at the University of Chicago to her roles at the National Symphony Orchestra and the Washington Ballet, Elvi shares her journey and contributions to the arts. She also discusses founding the Laurel Fund for Performing Arts and her continued retirement endeavors, including owning Curves franchises and promoting young artists. Dive into Elvi's inspiring story and explore how purpose and passion can shape a fulfilling life post-retirement.

00:00 Introduction and Sponsor Message

00:23 Guest Introduction: Elvi Moore

01:22 Early Career at the University of Chicago

02:44 Transition to Arts Administration

04:32 National Symphony Orchestra and Washington Ballet

06:12 Founding the Laurel Fund for Performing Arts

12:02 Curves Franchise Venture

15:49 Board Memberships and Book Clubs

17:30 Travel and Future Plans

19:12 Advice for Approaching Retirement

20:21 Conclusion and Sponsor Message