From Reflection to Action: Deborah Bennett’s Next Chapter Bloomed in the Leadership and Society Initiative
Combining community, care, and conservation through repurposed flowers
For leaders navigating the second half of their careers, the Leadership & Society Initiative (LSI) at the University of Chicago offers more than an opportunity for reflection. It offers a path forward. Dan Draper, CEO of S&P Dow Jones Indices, shares why he joined the LSI advisory committee and what makes the new Imagine Pathway such a powerful opportunity for today’s accomplished leaders.
A Pathway Built for Leaders in Motion
Designed for senior leaders who remain active in demanding professional roles, the LSI Imagine Pathway offers a structured yet flexible way to strategically pause, gain perspective, and envision what comes next. Through quarterly residential gatherings, Fellows engage in guided reflection, build enduring connections with peers, and explore how their values, experience, and expertise might shape a more purposeful future. Drawing on his experience as an advisor, Dan reflects on the purpose and promise of this new pathway.
“The LSI Imagine Pathway offers an incredible opportunity for leaders who are actively engaged in high-level roles across society,” Draper explains. “It brings all the intellectual rigor of the traditional LSI experience but adapts the format to fit the time constraints of executives.”
Over the course of a year, the fellowship’s four immersive sessions create the conditions for meaningful insight and lasting community.
“What’s most exciting about working with this group of leaders in LSI,” Draper shares, “is the reflection that happens when people from very different industries and experiences come together. You start rethinking your own assumptions and seeing past challenges as assets.”
At its core, LSI invites Fellows to think deeply about how their personal experiences can serve not only themselves or their organizations, but also the greater good.
A Liberal Arts Lens for Leadership
For Dan, the liberal arts are essential for any leader navigating complex systems: “You can’t lead effectively without empathy, without communication, without perspective,” he says. “The liberal arts offer a shared language and an intellectual compass. They help leaders see where they’ve been and imagine where they could go.”
That compass, Draper explains, is particularly critical at moments of rapid technological, political, and cultural change.
Realigning with Purpose
One of the most important shifts the Imagine Pathway supports is the move from extrinsic to intrinsic motivation. “A lot of leaders spend their careers chasing external recognition,” Draper notes. “But the Imagine Pathway gives you space to realign with your inner purpose. It’s about reconnecting to the ‘why’ that got you started in the first place.”
Draper emphasizes that this isn’t a passive experience, it’s an intentional way to help plan your next chapter. “This is an investment of time with tremendous return,” he says. “Yes, you grow as an individual, but your organization benefits, your team benefits, and society benefits. It’s not just about thinking differently. It’s about acting differently.”
And as Draper puts it, learning shouldn’t stop when your current career chapter ends. “With AI and evolving technology, leaders now have access to more tools and resources than ever. The real challenge is imagining how to use them for meaningful impact.”
A Scaffold for Your Next Chapter
The LSI Imagine Pathway is a carefully curated experience, providing reflective moments of pause for Fellows who are still engaged in day-to-day responsibilities and want to begin envisioning what’s next.
“It’s like scaffolding,” Draper says. “You may be building something that’s never finished, but with the right support, you can build higher, stronger, and more responsibly. And help others build after you.”
When asked what he hopes every Fellow takes away, Draper was clear: “I hope they come away more humble and more brave. Braver about facing the big challenges, about acting with purpose, and about creating change that lasts.”
Through LSI’s rigorous curriculum, Fellows engage with eminent faculty and expert practitioners to explore how their next chapter can be meaningful for them and for society. This fellowship is a commitment to personal growth, enduring wellness, and dynamic engagement with pressing societal issues. Contact us to learn more about LSI.
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