Introduction: When Life Forces a Reset

What happens when everything you’ve built—your career, your identity, your expectations gets stripped away? For Diana Place, that moment didn’t come gently. It came as a series of what she calls “lightning strikes”: a cancer diagnosis, the loss of her business, her daughter leaving for college, and the milestone of turning 60.

Rather than crumble, Diana transformed. She used these pivotal moments as the foundation for her next chapter—what she now calls her Third Act Quest. Through this movement, Diana is helping women over 50 reframe what aging means, reconnect with their passions, and reclaim their power.

A Career of Reinvention: From Advertising to AOL

Diana’s early career was fast-paced and filled with creativity. She began at an ad agency in the 1980s, a time she remembers fondly. “It was wild,” she said. “I literally got headlines for a campaign on a cocktail napkin.” The agency world was thrilling and spontaneous, so much so that Diana jokes about the creative director being at the bar when the client arrived. Yet despite the excitement, she often felt like she was “dancing on the edges” of her passion, holding back from fully expressing her ideas out of fear.

After a decade, Diana had a defining moment on a sidewalk. She asked herself, “What am I doing with my life?” That question pushed her to leave the agency world and launch her own cause marketing firm, blending her business acumen with purpose-driven initiatives. She worked to create partnerships between public and private sectors, hoping to make a difference through her professional skills.

Then came the internet. Diana was offered a job at America Online (AOL) in the late 1990s, and even though it meant taking a 50% pay cut, she jumped at the opportunity. “I had a feeling this internet thing might be something,” she said. At AOL, she helped launch one of the first online brokerage platforms and believed deeply in the power of the web to democratize access to knowledge and opportunity. “If a pregnant teenager needed information, she could go online. That mattered to me.”

A Series of Lightning Strikes

Diana’s transformation wasn’t a slow burn. It came suddenly—and all at once.

First came a cancer diagnosis. Then, the closure of her business. Her daughter was preparing to leave for college. She was turning 60. These weren’t minor life changes. They were full-body jolts.

“I sat down and realized I had a clean slate,” she said. “This is your third act.” With that clarity, the Third Act Quest was born. It was never just about creating a platform. It was about creating a space where women could explore the question: What’s next?

The Birth of Third Act Quest and the 333 Collective

Diana launched the 333 Collective for “fiercely curious women over 50.” During the pandemic, she held over 25 Zoom events where women told their stories of disruption, reinvention, and resilience. These weren’t celebrities. These were women in their 50s, 60s, even 90s, who had reimagined their lives and dared to do something new.

She eventually took the gatherings offline. In May, she hosted the first in-person Quest Gathering to celebrate the 333 Collective. “I was blown away,” Diana shared. “Eighty women came. Many had never even heard of me before—something popped up on LinkedIn or online, and they just showed up.”

What surprised her most? “They didn’t come because of the speakers,” she said. “They came because they wanted to be with each other. When they walked in, it wasn’t about business cards or credentials. It was: ‘Hey, how are you? What’s your story?’”

Building a Movement Through Stories

Diana believes storytelling is at the heart of transformation. She’s now launching a video storytelling series featuring women who’ve crafted unique Third Acts. “It’s a way to archive these experiences,” she said. “So many of us forget who we were when we were young. Storytelling brings that part of us back.”

At one Quest event, she led an exercise called “Flashback to Five,” asking participants to share memories from age five. “At first people said, ‘I don’t remember anything,’” Diana said. “But soon the stories came flooding back. It’s a way to reconnect with the core of who we are.”

Collaboration Over Competition

Diana’s philosophy is deeply collaborative. “In the corporate world, women were often pitted against each other,” she said. “But I think that dynamic is shifting. Women over 50 are choosing to co-create and cheer each other on.”

She recalls conversations with Leslie Jane Seymour and other women in media who agree that it wasn’t the women themselves—it was the system that fostered competition. Now, Diana is actively building bridges, not walls. “If someone’s doing similar work, I want to figure out how to collaborate.”

Intergenerational Mentorship and Reverse Learning

One of the unexpected joys of Diana’s work is how it connects generations. She frequently learns from her 23-year-old daughter, who’s fulfilling her dream of restoring coral reefs. “She inspires me daily,” Diana said. “And I call her for marketing advice, too.”

Diana is a fan of reverse mentoring, where younger employees mentor senior leaders. “There are companies like Estée Lauder doing this, and their retention rates are amazing. Younger people bring fresh insights. We all have something to teach each other.”

She cited filmmaker Melissa Davey, who released her second film at age 74. The most surprising feedback? Praise from 20-somethings who found the stories deeply relatable. “It’s proof that our experiences are universal,” Diana said.

Age as a Catalyst, Not a Limitation

“When people ask when I’m going to retire, I say, Why should I?” Diana said. “I love what I do.”

She encourages women to shed societal expectations and embrace their own timelines. “Our mothers had linear paths. That’s not us,” she said. “We’re redefining work, love, community—all of it.”

She aligns with anti-ageism activists who believe the most powerful protest is visibility. “We debunk aging myths by how we live,” Diana said. “We’re not fading. We’re thriving.”

A Message to Her Younger Self

If she could talk to her younger self at AOL, Diana knows exactly what she’d say: “You don’t have to work 20 hours a day to prove yourself.”

She believes her cancer diagnosis was her body’s final warning. “I was a productivity junkie,” she said. Now, her success metrics are joy, ease, and alignment.

The 10-Year Vision

Diana’s vision for the future is rich and intentional. She imagines local Third Act hubs in at least 20 cities around the world. Each community would host storytelling events, in-person meetups, and collaborations that keep women inspired.

She’s also developing a massive digital library of stories—an archive where women can submit their journeys and be seen. “We need to hear these stories,” she said. “We need to remember we’re not alone.”

Final Thoughts

Diana Place didn’t wait for permission. She turned four lightning strikes into a movement of meaning. Her message isn’t just for women over 50—it’s for anyone facing reinvention.

“You’re not too late,” she said. “You’re right on time.”

Watch her full episode here:

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