At the Southwest Organizing Project (SWOP), leadership is not treated as something people are simply born with. It is something that is developed, sharpened, and strengthened through reflection, shared experiences, and collective learning. That spirit was at the center of SWOP’s recent Leadership Development Classes, where organizers and leaders gathered to deepen their understanding of organizing and reconnect with the values that guide their work every day.
The first session focused heavily on participants’ “why” — the personal motivations that moved them into organizing and community work in the first place. Leaders reflected on the experiences, people, and moments that shaped their commitment to fighting for stronger communities. The session also laid the groundwork for what participants hoped to learn throughout the classes, including key tenets of organizing such as reflection, power analysis, understanding the difference between a problem and an issue, and learning how to effectively share personal stories in organizing spaces.
The conversations created space for both newer and experienced leaders to reconnect with the purpose behind their work while identifying the skills they wanted to continue strengthening. Rather than approaching organizing as a fixed set of strategies, the session encouraged participants to view leadership as a continual process of learning and growth.
The second session built on those reflections by diving deeper into how organizers communicate and engage with their communities. Participants explored an important question: How do we convey what we teach to our community members?
Through discussion and dialogue, leaders examined the role tension plays in organizing work. Facilitators emphasized that tension is not something to avoid, but often a sign that people are engaging in meaningful and self-involving conversations. Leaders reflected on how to communicate in ways that genuinely express what matters to them and how authenticity helps build stronger relationships within communities.
Another major focus of the session was power. Participants discussed power not as something inherently good or evil, but as “the ability to act” — something that is consensual, collective, and relational. Leaders explored how definitions of power can shift depending on a person’s values and perspective, while also reflecting on how SWOP’s own understanding of power is rooted in community relationships and collective action.
The session also encouraged participants to acknowledge the people and experiences that led them into organizing work. Through a “River of Life” activity, several leaders shared
deeply personal stories about their journeys, highlighting the challenges, relationships, and defining moments that shaped them into the leaders they are today. The exercise created opportunities for vulnerability, connection, and deeper understanding among participants.
For many in attendance, including seasoned organizers, the classes served as an important reminder that leadership development is an ongoing process. When asked why it remains important for him to participate in these sessions even after years of organizing experience, Joel Rodriguez reflected on the value of continuing to sharpen the skills organizers rely on daily.
“This is about refining the tools that we use every day — tools that allow us to demonstrate real power through organizing,” Rodriguez shared. “Pausing and reflecting on these skills with leaders is an important part of the process to make sure we are doing the right thing.”
Rodriguez also emphasized that the classes are not just about skill-building, but about strengthening relationships among leaders who have shared important moments together throughout their organizing journeys.
“This is also building community,” he continued. “We have so many leaders here who we have cried together and fought together with. We have been together for really important moments of our lives so it's essential that when we do reflect, we do it together.”
As the Leadership Development Classes continue, SWOP leaders are not only strengthening their organizing skills, but also reinforcing the relationships, values, and shared sense of purpose that continue to drive community change across Chicago’s southwest side.
