Dear Friends -

A few weeks ago, I sat down with someone whose work I’ve admired for years: Rishad Tobaccowala. You may know him from his decades at Publicis Group, where he helped shape one of the world’s biggest communication and marketing organizations. Or maybe you’ve read his bestselling books Restoring the Soul of Business or Rethinking Work. Or perhaps you’re one of the 30,000+ people who read his weekly Substack, The Future Does Not Fit in the Containers of the Past.

Rishad has spent a lifetime helping people see, think, and feel differently about change. And now, in his own “company of one,” he’s modeling what it looks like to create a vibrant next chapter—one filled with purpose, connection, curiosity, and continuous growth.

Our conversation was packed with insight. Below are the pieces that stayed with me, because they speak directly to what so many of us are navigating: who we become when the career chapter ends, and how we design what comes next with intention.

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When I asked Rishad about the most important lesson he learned during his decades in leadership, he didn’t hesitate:
“Leadership isn’t about your zone of control. It’s about your zone of influence.”

A title may grant authority, but the ability to shape thinking, develop talent, and stay relevant comes from how you show up—not the org chart. This mindset becomes even more important when you transition out of a big role. Influence carries forward. Control rarely does.

This is a subtle but powerful reframe for Act Three planning:
your leadership doesn’t end when your title does.

This part of the conversation hit home.

Rishad shared that before leaving Publicis, he read a book called Retirement and Its Discontents. It follows five people through their first year after retiring—a doctor, teacher, construction worker, CEO, and more. What matters most isn’t money. It’s whether you maintain:

These are the exact pillars I work through with clients, and hearing him echo them with such clarity was validating. In his case, he intentionally built bridges before he left. He wrote a book, stayed partially connected to Publicis, created new communities, and designed new ways to grow.

Act Three doesn’t happen by accident.
It needs scaffolding. It needs thoughtfulness. It needs a plan.

One of the most painful truths he named was this:

People often confuse their popularity with their title and their budget.

When the title goes away, many discover that the attention they received wasn’t about them at all. Losing this external validation can be deeply destabilizing.

Rishad avoided the worst of this because, in his final years at Publicis, he no longer controlled budgets or clients. His relevance came from his ideas, not his power.

That became the foundation of his next chapter.

For those approaching retirement or reinvention, this is worth sitting with:

I loved this moment:

He described a piece he once wrote inspired by the line on author Arthur C. Clarke’s gravestone:
“He never grew up.”

It wasn’t about immaturity—it was about staying open, evolving, learning.
“You can be 25 and already dead,” he said,
“and you can be 75 and more alive than ever if you’re still learning.”

This is the heart of Act Three design. Your next chapter should stretch you. It should challenge you. It should expand your world.

The seasoned ones, as he calls us, don’t age out of relevance.
We age into possibility.

Though he calls himself a “company of one,” he’s anything but alone.

He creates content. He teaches. He speaks around the world. He collaborates with talented producers, editors, designers, and technologists—but none of them sit on his payroll. His ecosystem is fluid and modern. Lean, but powerful.

This is an inspiring model for anyone imagining an independent path in Act Three:
you don’t need a corporation behind you to do meaningful work.
You need curiosity, clarity, and the willingness to keep learning.

The part that will stay with me the longest was this:

“What brings me joy is making, building, and teaching.”

He writes his Substack every week.
He hosts two shows:

He speaks everywhere.
He thinks deeply about how the world is changing and how people can continue to matter within it.

It’s a generous body of work, and he views it as a service.
Even his free newsletter reaches more people than most keynote stages ever could.

That, to me, is Act Three at its best:
a chapter where your wisdom becomes your contribution.

His work is a goldmine. Start here:

🔹 Website: https://rishadtobaccowala.com
A full hub for his books, essays, podcast, and speaking.

🔹 Weekly Thought Letter:
The Future Does Not Fit Into the Containers of the Past
A sharp, eclectic, weekly read for leaders, creatives, and curious minds.

🔹 Books:
Restoring the Soul of Business
Rethinking Work (his newest)

🔹 Podcast: What’s Next?
Conversations about the world ahead.

🔹 The Rethinking Work Show (YouTube):
Interviews with innovators shaping the future of work: https://rethinkingwork.io

Watch/listen to our entire interview:

Rishad’s story offers a real blueprint for leaving one chapter with grace and entering the next with intention. His path reflects the very things so many of us crave:

That’s what Act Three is all about.

If you’re thinking about your own transition—whether it’s six months away or six years out—I’d love to help you shape it with the same clarity Rishad brought to his journey.

You don’t need to navigate the identity, purpose, and lifestyle questions alone.
This stage is too important to leave to chance.

Learn more about my practice here: goodmorningfreedom.com

Warmly,
Cara Gray
Third Act Consultant, CPRC, CEPA

P.S. If you want to start planning your third act, set up a time on my calendar for a chat: Schedule a Chat with Cara