Gabby Bennett '20 helped lead Wesleyan Volleyball to the program's first NESCAC Tournament title and first NCAA Elite Eight appearance. Today, she is a licensed social worker, an Adult Generalist Post Graduate Fellow at Wellington Counseling Group, and the founder of Cross Court Connections, a nonprofit that uses volleyball to address equity gaps in college access and athlete development. The connection between those roles is tighter than it sounds. It begins with what volleyball taught her about pressure, belonging, and the difference between surviving a system and changing one.
Bennett says the foundation for her path was laid long before college. Her family demanded excellence. Discipline was expected, not optional, and she was often placed in spaces that were designed to challenge and stretch her. At the same time, she was frequently one of the only Black girls in those spaces. That reality built a certain backbone. She learned how to perform under pressure, move through discomfort, and keep going even when she felt unseen. Just as importantly, it made her reflective. Volleyball became the lens through which she started to understand systems, opportunity, and performance, and later, the basis for asking a bigger question: what becomes possible when talented people get the support, structure, and access they actually need?
At Wesleyan, that question became real. Bennett still remembers coach Ben Somera calling her as a recruit and talking about changing the culture, hanging banners, and building something different. At first, it was a vision. Then it became a standard. By the time Wesleyan reached the Elite Eight and NCAA appearances started to feel like expectation rather than exception, she and her teammates understood they were not just winning matches. They were changing what people thought Wesleyan Volleyball could be. She often comes back to a speech her captains gave at the Elite Eight: as first-years, they were 1–9; as seniors, they were playing on one of the biggest stages in Division III. That kind of jump does not happen by accident. It happens through belief, discipline, and a group of people staying committed to something bigger than themselves.
Her own experience as a four-year starter taught her that perseverance is not just about pushing harder. It is also about knowing what you are sacrificing and why. One of the ideas that stayed with her most came from coach Ben: "Sacrifice is about giving up something you want for something you want more." Over four years, she had to define what her "more" was, especially while managing pressure, expectations, and injury. She learned to lower the stakes in her own mind when needed, to laugh, to zoom out, and to remember that she was choosing to play. That perspective helped her compete with more freedom and taught her that being a good teammate is not always about being the loudest voice. Often, it is about consistency, communication, and doing your role well even when it is not the most visible one.
That same way of thinking carried into the classroom. Bennett's dual major in Psychology and Education Studies helped her understand people from both directions. Psychology helped her think about what happens inside people: thoughts, emotions, identity, performance, and the hidden weight high achievers can carry. Education Studies widened the lens and showed her how schools, teams, and institutions shape belonging and outcomes from the outside. Taken together, those fields helped her see that environments are never neutral. They can help people expand, or they can quietly teach them to shrink. Social work, she realized, offered a way to connect those questions to action. It felt less like a pivot and more like the next step in the same inquiry she had already started at Wesleyan.
Service has always been part of that picture. Bennett traces her leadership instincts back to St. Ignatius College Prep and its call to be "a person for others," but Wesleyan deepened that commitment. Whether she was serving as a peer tutor, resident advisor, student intern, or helping build student leadership spaces, she came to see leadership and service as inseparable. They both ask the same thing: are you paying attention to what people need, and are you willing to help make the space better for the next person? That mindset followed her to the University of Chicago, where she served in student government while completing her social work training and later was named an Obama Foundation Scholar.
Before that, though, she spent time in corporate settings, including Goldman Sachs and Mesirow. Those roles were formative, especially because they taught her how systems operate, how leadership is developed, and how much organizational culture shapes people's lives. She worked on leadership development and DEI-focused initiatives and learned a great deal about professionalism, strategic thinking, and high-performance environments. But she also realized something important: scale is not the same as alignment. Being in a large institution does not automatically mean you are making the impact you most care about. Over time, she felt more drawn to work that stayed closer to people's lived experiences, where she could see change happen in a direct and human way.
That realization shaped Cross Court Connections, the nonprofit she founded to use volleyball as a vehicle for college access, leadership development, and equity. Bennett has seen how often the sport mirrors the admissions process itself. From club fees and recruiting travel to private coaching and insider knowledge, access is uneven from the start. Too many talented athletes get filtered out early because they lack resources, information, or high-quality instruction, not because they lack potential. She also points to gaps in coaching competency, emotional awareness, and assumptions about what a "college athlete" is supposed to look like. Her work aims to close those gaps by making support more transparent and holistic: technical training, recruiting education, academic preparation, leadership development, and honest conversations about fit, identity, and confidence.
Coaching, she says, has changed how she sees young athletes. She no longer sees them only as players, but as people building habits, beliefs, and identities they will carry long after sport ends. She wants them to think about values early, not just goals. She wants them to learn that perseverance should be purposeful, not empty. She wants them to understand that leadership is not always loud; sometimes it looks like accountability, emotional regulation, steadiness, and the ability to make others around you better. In that sense, volleyball becomes more than a game. It becomes a place where agency, resilience, and self-awareness can start to take shape.
Being selected as an Obama Foundation Scholar helped confirm that this kind of relational, community-based work is not small. It is systems work too. Bennett says graduate school helped her understand that the macro and micro are deeply connected. The one-on-one work she does with individuals and communities is not separate from broader change. It is one way into it. The recognition gave legitimacy to a path that does not always look obvious from the outside, especially when that path runs through social work, coaching, and volleyball.
Her message to young women of color navigating college, sport, and leadership is clear: swing big. Take the shot. Trust that you are building the tools you need as you go. She wants them to know they do not have to shrink to belong, and that the right environments are the ones that let them grow without losing themselves. Her own journey keeps circling back to the same belief: talent matters, but support matters too. When both are in place, people do not just survive pressure. They become something larger than it.
