Charting New Paths: Chicagobility Interns Explore Maritime Careers on Lake Michigan
July 30, 2025
by Maggie Shea and Annie Thompson
From July 7–11, the Chicago Yacht Club Foundation hosted 19 Chicagobility interns––teens ages 14 and 15 participating in the City of Chicago’s One Summer Chicago program––for a weeklong introduction to maritime careers and on-the-water safety training. These interns stepped away from their regular summer programming with Union League Boys & Girls Clubs to participate in an immersive crash course and explore the maritime industry’s many career pathways.
On the water, participants experienced firsthand what it means to work as a team on the boat, building confidence through boating safety drills, such as man-overboard recovery. Instructors underscored the importance of clear communication and decisive leadership on a sailboat. As teens took the helm, they began to see themselves not just as sailors, but as capable leaders responsible for the safety of their peers––a level of accountability and trust that is uniquely fostered through sailing.
Off the water, every day featured different professionals from across the maritime sector in daily “lunch & learn” conversations and presentations. Speakers shared insights about their roles and offered practical advice about pursuing a career connected to the water. As many of the teens were participating in their first paid job, the week kicked off with a financial literacy session led by Jesus Hernandez from the Wintrust Financial Literacy Team, who walked interns through the basics of budgeting and setting up a bank account. Martin Heft, bosun and boat rigger at Chicago Yacht Club, shared humorous (and occasionally chaotic) stories from his time both breaking and repairing boats––tracing his journey from the Rickover sailing program to a career he’s so passionate about that he said he’d “still work on boats even if he won the lottery.” Jeremy Jacques, dockmaster at Chicago Yacht Club, highlighted the transferable skills he brought from his original aspiration to be an architect, and spoke to the importance of developing a strong work ethic early in life. Later in the week, Michael Kemp, Nate Saint, and Rakeem Brown of the Illinois Department of Natural Resources brought contagious energy as they introduced outdoor career opportunities rooted in conservation and fishing.
The week wrapped with an inspiring conversation featuring Gina Rodriguez, harbormaster at 31st Street Harbor, and Jasmine Perez, dock manager. Jasmine spoke candidly about being a woman in a male-dominated field. Gina reflected on how her path shifted from aspiring teacher to harbor leader, illustrating how early goals can evolve into unexpected and fulfilling careers.
Across the board, guest speakers emphasized that there’s no single path to success. They encouraged interns to stay curious, embrace new opportunities, and pursue what inspires them. From harbor operations and boat maintenance to environmental conservation and financial literacy, participants came away with a broader understanding of the diverse career possibilities on and around the water. By introducing young people to job opportunities in the maritime industry early and providing meaningful, skill-building experiences, the Foundation aims to spark interest and help youth envision themselves as part of Chicago’s maritime future.