With over 30 years of leadership, Deborah shares her insights on this year's Leadership and Society Initiative (LSI) Fellowship and the path that has shaped her impactful work.
With more than 30 years of experience in place-based philanthropy and community-development, LSI Fellow Deborah Bennett has been a leading voice and respected grantmaker, working alongside foundations, government agencies, nonprofits, and community leaders throughout Chicago and beyond.
We recently had the privilege of sitting down with Deborah, to learn about her journey and experiences as part of the 2024-2025 cohort.
Deborah: It has been stimulating to be a part of the University, the intellectual community, and this cohort. We’ve been exposed to ideas and concepts that were pioneered by University of Chicago scholars and faculty, and continue to influence disciplines like economics, sociology, philosophy, and business. The exuberance of the professors is palpable. They are so excited about passing on their knowledge to us.
As a Chicagoan, I appreciate that many of our courses use Chicago as a learning lab. We’ve learned about issues like poverty, economic restructuring, residential segregation, and community-led change within the Chicago context. The immersion days have also been influential, as they provide an opportunity for in-depth learning about issues facing our city and the country, like gun violence, immigration, and citizenship.
Deborah: It has been great to be a learner again and to be a learner with some life experience. Instead of our courses being didactic, we engage in a dialogue with our professors around topics like individual rights, the role of government and philanthropy in society, ethics, meritocracy, and how these concepts apply to today’s real-world challenges. That combination of academic rigor and exploration with lived experience is very powerful.
Deborah: I was surprised at how quickly our cohort jelled. We genuinely like and respect each other. I have also enjoyed the philosophy and practical wisdom courses. Reflecting on what makes a choice-worthy life and observing themes across various ancient philosophies gives me comfort that there’s a way to live a flourishing life. Having purpose, balance, and virtue is key.
Deborah: The most challenging thing has been the uncertainty or ambiguity about my next phase. Generally, as a leader, you set a goal, then make a plan, and execute it. The whole point of the LSI experience is to take a step back and reflect. The encouragement to take the time for reflection and to embrace the unknown about the future has helped me deal with that anxiety.
Deborah: It’s the timing of the Fellowship that has been significant for me. It has been an antidote to the disillusionment that I feel about the contentious and polarized political period we’re in in our country and the erosion of the efforts of many past generations that have struggled to make our society more just. The LSI Fellowship is giving me hope.
In addition to the classes related to LSI’s three pillars: knowing yourself, understanding the world, and envisioning the future, we can audit classes. I audited an African American history course, which really gave me perspective. The way to justice is a constant push and pull. I’m glad to be in LSI at this time right now.
Deborah: My coach and I have discussed and explored different leadership styles. At this point in my life, I don’t want to necessarily be the one out front leading an initiative. I’m very interested in servant leadership, where power is shared and the well-being of others is the most paramount thing. I realized that I much prefer walking alongside another leader and working with a team of people who are trying to reach a common goal, and that’s okay. You don’t have to be the one out front.
Deborah: I do have an idea for a project related to gun violence. I’m looking forward to researching that further and writing about it. I also have an academic advisor in mind, and I am looking forward to engaging that faculty member for some input.
Deborah: As I mentioned, I have this idea and I want to determine the feasibility of it. The Fellowship has given me a deeper understanding, more of a historical understanding of the issues that are impacting Chicago. We talked about Chicago being a learning lab for many of our classes, and I anticipate that I will continue to serve on boards that are advancing community development, affordable housing, and racial justice in Chicago.
Deborah: I would tell them that the LSI Fellowship is an exciting opportunity that requires a significant amount of time and energy. If they can commit, I would encourage them to apply. There is power in different people from different sectors with different life experiences coming together to grapple with challenges. I’ve learned so much from my peers. As I’ve said, I have made some lifelong relationships. We are going to make a difference in the world.
Deborah: The beauty of the University of Chicago campus. It’s just a wonderful environment to be in. I love sitting on the quad and reading. I would also mention the University’s other resources. I’ve been to several lectures from the Institute of Politics, which have been very enlightening. It’s been exciting to be around undergrads as well. It gives me hope for the future.
The University of Chicago Leadership and Society Initiative (LSI) supports accomplished leaders in successfully transitioning from their longstanding careers toward purposeful next chapters. LSI Fellows immerse themselves in UChicago’s unparalleled environment of big ideas and multigenerational dialogue, gaining frameworks for learning from their past and planning for their futures.
Through LSI’s rigorous and customizable 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.
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.
The Leadership and Society Initiative welcomes two new team members, Michelle Argento and Kelly Morgan, who will strengthen recruitment and program operations as the Initiative continues to grow and expand opportunities for leaders pursuing purpose-driven next chapters.
Fellows returned to campus for four days of rigorous inquiry, renewed connection, and deepening clarity about the motivations and intentions for future leadership.