Takeaways from the July Imagine Pathway Retreat

Fellows in the Leadership and Society Initiative Imagine Pathway returned to Hyde Park for four days of rigorous inquiry, community, and deepening clarity about the next chapters they are working to shape.

In late July, the Leadership and Society Initiative (LSI) Fellows in the Imagine Pathway gathered at the University of Chicago for their third residential retreat of the fellowship year.  The July retreat invited Fellows to turn their attention outward, to consider the forces shaping the world, the challenges defining it, and the many forms meaningful leadership might take within it. 

The four days on campus were organized around two interlocking questions: What will the world look like in 2050? And what pathways exist for leaders who are ready to shape the future in significant ways? 

Arriving in Community 

The retreat opened with a visit to the Obama Presidential Center. The tour offered more than a cultural introduction, it grounded the retreat’s larger questions in a place shaped by the ideas of civic participation, collective action and community.  Michael Strautmanis, Chief Corporate Affairs Officer of the Obama Foundation, joined Fellows that afternoon to share the development and goals of the Center and its vision for impact on Chicago’s southside, opening a conversation about community-informed change and the responsibilities that accompany efforts to create lasting impact. 

The weekend was anchored by a mini course on Critical Inquires in Contemporary Philanthropy and Social Change, taught by Sampriti Ganguli, former CEO of Arabella Advisors and LSI instructor.  Each morning, Fellows engaged in a rigorous, session-by-session examination of modern philanthropy’s role, tools, and tensions in driving systemic change in the United States.  

Rather than offering a straightforward case for giving, the series pressed Fellows to grapple with harder questions: What makes philanthropy truly strategic? How do advocacy, collective action, and narrative change function as levers for systems level impact? And does philanthropy, by its nature, support or undermine democratic values? 

Drawing on decades of practitioner experience, Ganguli guided Fellows from the landscape of the giving sector through the mechanics of social movements and into some of the most consequential critiques of large-scale philanthropy. The course invited Fellows to consider not only what effective giving looks like, but also the responsibilities, limitations, and tradeoffs inherent in using private resources to pursue public change. 

The World in 2050: Rigorous Inquiry into the Future 

Friday and Saturday centered on a series of breakout sessions under the theme “The World in 2050,” in which Fellows chose between faculty-led explorations of the forces most likely to define the decades ahead. From climate to AI, capitalism to global conflict, the breakout sessions invited Fellows to examine consequential and often contested questions about the future of society. The goal: to position Fellows to anticipate the influences now that will create paradigms of the future in pursuit of contextualizing their own leadership decisions and priorities moving forward.  

Koichiro Ito, Professor at the Harris School of Public Policy, led a session on renewable energy expansion, examining the global energy transition and the key challenges and emerging opportunities on the path to decarbonizing society.   

Bernard Koch, Assistant Professor in the Department of Sociology, explored how artificial intelligence is radically reshaping the worlds of science and culture, accelerating the discovery and creation of ideas while, in some respects, narrowing how we think. 

 Yueran Ma, Carhart Family Professor of Finance at the Booth School of Business, traced the history and evolution of capitalism and invited Fellows to imagine its future and its implications for economies and societies.   

Paul Poast, Associate Professor of Political Science, examined today’s global disorder, exploring what a multi-polar international order may mean for conflict, cooperation, and leadership over the next 25 years.  

Aziz Huq, Frank and Bernice J. Greenberg Professor of Law at the University of Chicago Law School, led a session on the future of democracy and governance, investigating the forces shaping democratic institutions in an increasingly complex global landscape.  

Julia Behrman, Associate Professor of Sociology at Northwestern University, offered Fellows a complementary lens, exploring how shifting trends in birth rates and longevity will transform society in the years ahead. 

Across these sessions, Fellows encountered scholarly frameworks and evidence-based perspectives that challenged them to think more rigorously about the future and to consider how those forces might inform their own choices about leadership, responsibility, and contribution. 

Pathways to Impact 

Saturday afternoon brought the retreat’s other central inquiry into focus: not just what the world will look like but where and how Fellows might choose to act within it. Four breakout sessions introduced Fellows to distinct pathways for making meaningful impact, each led by a practitioner with deep experience in their domain. 

Buffy Higgins-Beard, Township Supervisor of Milton Township and LSI Fellow, offered a ground-level view of elected service and local government, exploring what it takes to contribute to public policy from within the civic sphere.  

Seth Green, Dean of the Graham School, led a session on social business that examined how enterprises can be structured to address pressing societal needs.  

Priya Parrish, Partner and Chief Investment Officer at Impact Engine, explored the landscape of impact investing and the role capital can play in driving social change.  

Kathleen Tamayo, Partner in the Board and CEO Practice at Spencer Stuart, offered a practitioner’s guide to strategic board service, helping Fellows understand how to evaluate board roles, develop their governance skills, and make meaningful contributions to organizations whose missions align with their values. 

Together, these sessions gave Fellows a chance to move from reflection toward possibility: to examine different avenues for contribution, ask what each requires, and consider which forms of leadership might align with their experience, values, and aspirations for what comes next. 

Community Across Cohorts and Generations 

One of the July retreat’s most distinctive features was its sustained integration of the broader LSI community. On Friday, Imagine Pathway Fellows were joined by Fellows from across all LSI cohorts for a community lunch featuring a conversation with Dennis Chookaszian, former Chairman and CEO of CNA Insurance Companies, hosted by Graham School Dean Seth Green. Chookaszian’s story of enduring leadership across a lifetime, and his willingness to speak with candor about what he has learned, offered Fellows something the schedule alone could not: a concrete example of what it looks like to lead with purpose over the long arc of a career and a life. 

Friday evening extended that spirit of community into a cross-generational conversation. Current University of Chicago students joined Fellows for “The Issues of the Future,” a panel moderated by Ravy Uong, Director of Civic Engagement at the Institute of Politics, in which students shared their biggest concerns and greatest hopes. Fellows and student leaders then continued their discussion over dinner, exploring together where leadership is needed most and what intergenerational collaboration could accomplish for a stronger future.  

 The exchange brought different stages of life into conversation around a shared set of questions: What kind of future are we creating? What responsibilities do different generations hold? And where might each person contribute? The discussion underscored a central idea of the retreat—that shaping the future is not the work of any one group, but a shared project. 

Closing with Clarity 

Saturday evening offered a different kind of highlight: a private architecture boat tour and catered dinner aboard the Little Lady, traveling along the Chicago River and watching fireworks off Navy Pier. It was a fitting close to a weekend spent thinking about large forces and long horizons; it was a moment of beauty and shared experience that reinforced what has become one of the Imagine Pathway’s most important features: the relationships Fellows are building with one another. 

Fellows left the retreat carrying new frameworks for understanding the world, stronger connections with one another, and new questions to carry into their own discernment about what comes next. The conversations will continue, as will the work of translating reflection into purposeful action. Through that process, the Leadership and Society Initiative will continue to support Fellows as they imagine and begin to shape their next chapters of leadership and contribution. Learn more about LSI by attending our upcoming information session

Category
About LSI