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 f...

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 observin...

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.