Dreaming Beyond the Boundaries: Jennifer Hodges Awarded Sixth Donald Stewart Fellowship

Jennifer Hodges is the co-founder and vice president of KIPP Chicago’s Whole Child Initiative, a program that supports students, teachers and families through a holistic approach aimed at removing barriers to student success. She is also a visual artist whose abstract mixed-media work explores the complexity of Black identity, particularly Black femininity. With a career spanning finance, nonprofit and education, she brings a creative lens to leadership and social impact.

In 2025, she became the sixth recipient of the Donald Stewart Fellowship, awarded annually by African American Legacy, an affinity fund of the Trust, to an individual embodying leadership in Chicago’s Black community. In an interview with the Trust’s Strategic Communications Intern Cora Fassett, Hodges shares insights into her career journey, the lessons she’s learned, and her vision for Chicago’s future.

Tell us about your career journey and how you got to where you are now.  

Jennifer Hodges: I describe myself as an artist, an alchemist, and a visionary leader—identities that reflect the layered, nontraditional path my career has taken. I’ve worked between the corporate, nonprofit, and now education sectors, with art as the constant thread connecting every phase of my journey.

My professional journey in finance started with a Michigan-based firm, Greenleaf Trust. Having grown up in Detroit myself, I saw it as a way to acquire the tools and knowledge that had been historically out of reach for people in my community. Working in the president’s office at Greenleaf Trust, I was privy to his impact and transformation on the North Side of Kalamazoo, a predominantly Black community, and became inspired and ignited by his impact.

That realization led me to the nonprofit sector, where I found deeper alignment. I moved to Chicago because it was and is the perfect blend of art and business. I joined United Way of Metro Chicago, where I fundraised for South and West Side communities, helping raise approximately $14 million annually. The work was deeply fulfilling, and I saw the direct impact of how my work in securing financial investment could transform communities. But I began to crave a closer relationship with the individuals and families we aimed to support. I wanted to hear their stories, understand their experiences, and witness firsthand the change we were working toward.

That desire brought me into the field of education. I joined KIPP Chicago to launch and lead the Whole Child Initiative, a program designed to support the overall well-being of students, families and educators. It’s a role that integrates all aspects of who I am—the artist, the advocate, and the community-centered leader—to benefit youth and adults.

Through every chapter of my career, creativity has remained my compass. Whether that’s creating a new path, drawing connections in seemingly disparate sectors, or creating something from scratch—be it a program to meet the needs of individuals to creating original works of art on canvas. It’s how I connect, how I lead, and how I reimagine what’s possible for the communities I serve.

What are some lessons you’ve learned in your career? 

JH: One of the most important lessons I’ve learned is to lead with purpose. My purpose statement: to use my creativity to elevate human potential for generational advancement is my compass for decision-making. It helps me discern between opportunities that are simply “good” and those that are truly right for me—aligned with my values, vision and mission.

Having a clear sense of purpose has allowed me to move through my career with intention and clarity. It keeps me rooted in my deeper “why,” which is a commitment to impacting lives authentically and creatively, not just in the present but for generations to come.

Are there leaders or icons, past or present, who inspire you?  

JH: Malcolm X is a major inspiration for me. His unwavering commitment to Black excellence and his continual process of self-reinvention deeply resonate with my own journey.

When I moved to Chicago, I created a vision board of leaders I admired and aspired to meet or collaborate with. At the very top was Michelle Boone—now CEO of the Poetry Foundation, but then serving as commissioner of the Department of Cultural Affairs and Special Events. I’ve always admired how seamlessly she blends strong leadership with deep engagement in the creative sector. Another person I hold in high regard is Connie Lindsey. She’s a powerhouse—leading with intelligence, grace and authenticity. As a Black woman in executive corporate leadership, it’s incredibly challenging to be effective, respected and warm all at once. Connie strikes that balance effortlessly.

As the Donald Stewart Fellow, you are awarded money to support your work. What do you plan to use it for?  

JH: I’m deeply honored to be selected as the Donald Stewart Fellow. What made this recognition especially meaningful was learning how closely Donald Stewart’s life mission mirrors my own with a shared commitment toward generational advancement. That alignment reinforces the purpose behind my work and gives this fellowship even greater significance.
I view the use of this award through the lens of time: past, present and future.

For the future, I plan on investing in my entrepreneurial and artistic endeavors, an inventive hiatus that includes international travel centered on artistic learning and creative exploration for my brand, Art. Life. Luxury. That will include exploring new creative markets and building the infrastructure to scale the business of my creative work.

In the present, I want to strengthen my financial foundation and continue investing toward sustainability.

To honor the past, I will support small nonprofits focused on education and creativity—especially those rooted in community work that aligns with the values I hold dear.

This award is more than funding—it’s a catalyst to deepen my impact, honor legacy, and build boldly toward what’s next.

Do you have a blue-sky vision for Chicago’s future, especially when thinking about the Black community? 

JH: My blue-sky vision for Chicago is for the Black community to dream beyond the boundaries of their lived experience, and for every individual to have the freedom and agency to achieve their dreams.

I’ve come to understand that real dreaming begins when you’re no longer in survival mode. When basic needs consume your energy, it’s hard to imagine a different future, let alone a bold one. I’ve been fortunate to have mentors, friends and community leaders who invested in me and helped me see beyond limitations and beyond what I thought was possible. That gift of vision and radical dreaming is something I now strive to implement and pass on to my son, my mentees, and the communities I serve.

Through my work, I aim to create spaces and opportunities where dreaming big isn’t just encouraged, it’s expected. Because when we equip people with the tools, resources and belief to imagine something greater, we unlock the full potential of our communities.