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.