
Re-Educated on Midlife Transition: A Conversation with Lucy Kellaway
In this conversation, journalist, author, and educator Lucy Kellaway discussed midlife transition, lifelong learning, and her book Re-Educated.
The University of Chicago Leadership & Society Initiative is pleased to announce the 2026 Fellows in its Imagine Pathway, bringing together accomplished senior leaders from across the private sector, government, and civil society. The cohort includes CEOs, board members, C-suite executives, and managing partners of global enterprises, as well as former cabinet-level officials, academic leaders, and internationally recognized experts.
“What stands out about this cohort is not only the scale of their accomplishments, but the curiosity and intention they bring to this moment,” said Seth Green, Dean of the University of Chicago Graham School. “These are leaders who have operated at the highest levels and are now choosing to engage in rigorous reflection. The Imagine Pathway creates a rare format that allows them to do that deep reflective work without stepping away from their ongoing responsibilities.”
These forty leaders share a common commitment: to discern how they can meaningfully focus their next chapters of leadership contributing to society. Through the Imagine Pathway, these LSI Fellows will convene for quarterly retreats on the university’s Hyde Park campus, reflecting on their values, strengths, and passions while engaging with perspectives on the world’s most pressing challenges—and the most promising paths forward.
“I have been asking myself ‘What’s Next?’,” reflects Lyell Clarke, Chairman of the Board of The Clarke Company, who recently finished his tenure as the company’s CEO. “I want to develop a plan for this next chapter that allows me to do as much good as I can, for as long as I can. This fellowship has come at the perfect time to explore those options and begin to visualize the path forward.”
This cohort of Fellows shares a readiness to engage in rigorous inquiry, of both self and of society, at a pivotal stage of leadership. Actively engaged in their fields, they come to LSI with a common aspiration: to consider how their experience, influence, and values can be directed toward meaningful impact in the years ahead. This group’s aspirations for their next chapter are as diverse as their backgrounds and experiences. They are considering next chapters that range from strengthening healthcare access and food security to addressing global conflict, political polarization, mental health stigma, long-term unemployment, and the development of young leaders.
The Imagine Pathway is a curated fellowship experience designed for leaders who remain deeply engaged in their day-to-day responsibilities and seek intentional moments of pause to reflect, recalibrate, and imagine a fulfilling future. Meeting quarterly, Fellows come together to examine their experiences, explore emerging possibilities, and envision purposeful next chapters grounded in their values and aspirations.
“I’m looking forward to the opportunity to step out of the day-to-day pressures of my schedule and spend time being thoughtful and intentional about what lies ahead in my leadership journey. Too often, the demands of leading an organization take priority over creating space to be strategic about my own development,” says Robert Diaz, Executive Vice President & General Counsel of National CORE, an affordable housing developer in Southern California.
Through a carefully designed learning journey situated within UChicago’s environment of intellectual freedom and field-defining scholarship, the LSI Fellows in the Imagine Pathway gain access to the structure, perspective, and resources needed to clarify their motivations, broaden their thinking, and apply new insights to both their current roles and their evolving futures.
Jennifer Tescher, Founder & CEO of the Financial Health Network, is looking forward to learning alongside the cohort. “I am excited for the rare opportunity to engage with a group of people wrestling with the same questions I have about finding new ways to contribute our time and talents to pressing societal issues. The LSI fellowship offers a structure for exploring the relevant frameworks that will help guide our journey.” Through engagement with the University’s eminent faculty and participation in a robust peer-learning community, Fellows deepen their discernment through structured dialogue, ideation, and feedback. This collective exchange, rooted in trust, curiosity, and shared purpose, enables Fellows to test ideas, gain clarity, and expand how they define contribution and impact while remaining fully engaged in their professional lives.
“I’m pursuing LSI because I want to earn the skill to craft the next act of my life into one of service and scale,” said Aki Hussain, co-founder and chief legal compliance officer at Terrapay. “And I want to do it surrounded by—and guided by—people who have chosen impact over inertia. The LSI fellowship speaks to me because it’s rigorous. It demands self-awareness, curiosity and moral courage.”
Spanning industries including health care, education, finance, technology, life sciences, law, and international development, the incoming Fellows in the Imagine Pathway represent a wide spectrum of leadership experience and executive distinction. Members of the cohort have led major corporations, advanced innovation in global enterprises, guided prominent educational institutions, and overseen complex civic organizations. Representing multiple countries and more than a dozen U.S. states, the Fellows bring deep global leadership experience and a diversity of perspectives that will enrich classroom dialogue and strengthen the collective impact of the Initiative.
“The Imagine Pathway was designed for leaders who are still very much in motion, carrying responsibility, influence, and impact, yet who recognize the value of stepping back in order to move forward with greater intention,” said Diana Petty, Executive Director of the Leadership and Society Initiative. “This inaugural cohort brings a rare combination of accomplishment, openness, and seriousness of purpose that will shape a powerful learning community, and we’re truly honored to be expanding the ways we can support leaders in this distinct stage of life.”
LSI will welcome the Imagine Pathway Fellows to campus this January as they join a growing community of leaders engaged in reflective inquiry and purposeful action. The inaugural cohort reflects both the momentum of the Initiative and the shared possibilities ahead. To learn more about this new cohort please view our current Fellows page.