Exploring Philanthropy’s Path Forward: Insights from the 2024 Philanthropy Leads Conference

Indiana Philanthropy Alliance’s (IPA) 2024 Philanthropy Leads Conference gathered leaders and changemakers from all corners of philanthropy, including corporate, community, and government sectors, in a powerful show of collective vision and innovation. 

The conference offered a unique opportunity to discuss critical issues facing philanthropy today, while fostering collaboration across Indiana’s philanthropic ecosystem. 

As Debra Jacobs, President and CEO of The Patterson Foundation, expressed, “Being part of IPA's conference is an incredibly energizing opportunity because not only am I going to get to share what keeps me up at night and what gets me out of bed energized in the morning, but I'm going to be able to learn from others...that learn where you are, listen to others, embrace possibilities. The who else cares and what's possible should undergird all of our work in philanthropy.”

The conference’s plenary lunch session, led by distinguished philanthropic figures including: Dr. Leslie Lenkowsky of Indiana University, Debra Jacobs of The Patterson Foundation, Philip Li of Robert Sterling Clark Foundation, and Mary L. Thomas of CFLeads, brought a wealth of experience to address vital questions about the future of philanthropy, engagement with communities, and advice for future generations of philanthropic leaders. 
 

In the planning stages of the 2024 Philanthropy leads conference, IPA staff asked these three leaders the following questions: 

1.    How do you engage with and learn from the communities you serve?
2.    What keeps you up at night about the future of philanthropy?
3.    What advice would you give to your past self at the beginning of your career?

Learn more about their outlooks and approaches to philanthropy in this article.

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How do You Engage with, and Learn from the Communities You Serve?

Debra Jacobs, who took on the role of President and CEO of The Patterson Foundation in 2009, has championed creative collaboration throughout her career. For Jacobs, engaging with communities means going “beyond the desk.” 

She noted, “If we don't go out into community, we will miss an opportunity to learn where people are.” Under her leadership, The Patterson Foundation has strengthened its impact by combining face-to-face interactions with digital communication strategies that foster accessible, two-way engagement.
 

Leslie Lenkowsky, an Emeritus Professor of Public Policy and Philanthropic Studies at Indiana University, has a storied career in civic engagement and philanthropy, including serving as CEO of the Corporation for National and Community Service under President George W. Bush. Although now observing from a more detached position, Lenkowsky shared his belief that a strong relationship between philanthropy and community is essential. 

“A good philanthropist must be more than a giver,” he said, reminding attendees that philanthropy’s privilege requires the highest purpose and utmost care in engagement.
 

Mary L. Thomas, President and CEO of CFLeads, has over 25 years in the community foundation field. Her passion for amplifying community voices through grassroots leadership and her dedication to racial equity have been hallmarks of her work. Thomas explained that to truly empower communities, philanthropists must be present and responsive to local needs. 

“If we’re going to strengthen individuals, organizations, and communities, we need to be where the people are,” she emphasized, advocating for a community-centric approach to leadership development.
 

What Keeps You Up at Night Regarding the Future of Philanthropy?

Each speaker voiced concerns about philanthropy’s future, while offering unique perspectives on how to approach these challenges.

For Jacobs, the future is not a source of fear but of motivation, saying, “There are immense opportunities for philanthropy to make a positive impact.” She encouraged her colleagues to meet each day with intention, seizing opportunities to create meaningful change.

Lenkowsky voiced his concerns about the sector’s evolving nature, saying, “What I most worry about is that we may have lost too much of the personal side of giving and volunteering.” As a leading scholar on civic engagement, Lenkowsky fears that the rise of institutional philanthropy may overshadow the human connections that define civil society, an aspect he believes is essential to philanthropy’s role in building community.

For Thomas, the continuity of leadership in the sector is paramount. She reflected on the urgency of cultivating the next generation of leaders, saying, “What will leadership look like 20 or 30 years from now? What is my role and responsibility in helping to nurture the next generation?” Thomas’s concerns about succession reflect a broader call to action to ensure the philanthropic sector remains robust and adaptive for decades to come.

 

What Advice Would You Give Yourself at the Beginning of Your Career?

Reflecting on their early years, each speaker shared valuable lessons they would impart to their younger selves. 

Jacobs advised staying humble and embracing collaboration. “Understanding you can do nothing alone,” she said, is a principle she has relied on throughout her career. Her experiences underscore the power of collective action and shared aspirations.

For Lenkowsky, whose career path began serendipitously, the lesson was about humility and curiosity. He cautioned newcomers to resist the allure of perceived expertise that may come with working in affluent settings. “Always remember there is a lot you do not know,” he advised, urging young professionals to keep learning and questioning.

Thomas emphasized the importance of gratitude and community. With her experience in grassroots leadership, she encouraged her younger self to embrace the spirit of collaboration, understanding that progress is a series of lessons “Learn as you go, and don’t take things too seriously,” she said, highlighting the value of each phase in the journey.