Act Three

Cara Gray
  • 5.0 (8)
  • HOBBIES
  • UPDATED WEEKLY

The past few years have caused many of us to rethink how we live our lives. And for those of you approaching retirement, the question becomes more urgent - now what? How do you find new meaning and purpose? I'm Cara Gray, a consultant, multi-passionate entrepreneur, and seeker of life's answers. Join me as I explore inspiring conversations with those thriving in their "third act." Hear first-hand as former and current executives, professionals, and creatives share their authentic journeys of self-discovery. Learn how they forged new identities, found community, manage wellness, and uncovered what makes them feel alive. And though each story is unique, they all paint a hopeful picture of how to live with purpose, passion, and vitality at any age. Join me each week as I unlock wisdom and insights from those thriving in Act Three. Because it's never too late to thoughtfully shape the rest of your life.

  1. 12/07/2025

    Rishad Tobaccowala on How to Design a Meaningful Act Three

    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.

    34 min

  2. 10/08/2025

    Embracing Age Inclusivity with Jacynth Bassett | Act Three Podcast

    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/

    30 min

  3. 08/24/2025

    The Four Pillars of Aging Well | Allison O'Shea on Staying Independent, Prepared & Confident

    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.

    31 min

  4. 07/14/2025

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

    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

    46 min

  5. 05/12/2025

    Dr. Karen Falkenberg's Journey from Chemical Engineer to Strength Training Advocate

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

    36 min

  6. 04/21/2025

    Embracing Life's Third Act with Ann Medlock

    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

    29 min

  7. 03/24/2025

    Embracing Transformation: Alicia Johnson on Wonder-Based Trauma Recovery and Reinvention

    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/

    46 min

  8. 02/27/2025

    Finding Purpose through Service and Courage with John Graham

    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/

    33 min
See All (37)

Trailer

Ratings & Reviews

5
out of 5
8 Ratings

About

The past few years have caused many of us to rethink how we live our lives. And for those of you approaching retirement, the question becomes more urgent - now what? How do you find new meaning and purpose? I'm Cara Gray, a consultant, multi-passionate entrepreneur, and seeker of life's answers. Join me as I explore inspiring conversations with those thriving in their "third act." Hear first-hand as former and current executives, professionals, and creatives share their authentic journeys of self-discovery. Learn how they forged new identities, found community, manage wellness, and uncovered what makes them feel alive. And though each story is unique, they all paint a hopeful picture of how to live with purpose, passion, and vitality at any age. Join me each week as I unlock wisdom and insights from those thriving in Act Three. Because it's never too late to thoughtfully shape the rest of your life.

Information

  • Creator
    Cara Gray
  • Years Active
    2023 - 2025
  • Episodes
    37
  • Rating
    Explicit
  • Copyright
    © 2025
  • Show Website
    Act Three