- December 13, 2025
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For 25 years, business owners, entrepreneurs and community activists alike have been signing themselves up for a challenge — and what each of these hopeful pioneers have in common is a drive for leadership.
Once a month, Leadership Winter Park meets for themed day-long sessions where participants discuss and debate critical issues, from healthcare to the evolution of education, and tour Winter Park's essential resources and little-known niches: the police department, the Crealdé School of Art, and local elementary schools. They use these whereabouts for hands-on activities, such as shadowing firefighters and helping with mock emergency situations for in-your-shoes experiences to get them to know their neighborhood professionals.
Leadership Winter Park will celebrate its 25 anniversary with a gala at the Alfond Inn on Friday, May 15, at 6 p.m. The cost is $75 per person, or $125 per couple. The event is black-tie optional. For more information, email [email protected]. To register, visit http://conta.cc/1DF7P1v. The RSVP deadline is May 8.
While leadership ventures aren't new to Mark Freid, a 2013 graduate of the program, the monthly dosage of discussion and tours were beneficial for keeping him "in the know" and inspired him to keep reinventing the wheel when it comes to running a business.
"Growing a business means learning how to evolve as a leader — relinquishing some power and control and give that over to other team members," said Freid, who is the founder of the local advertising agency Think Creative. "I have a very simple definition of leadership: What conversations happen because you're in the room?"
Leadership Winter Park began as a simple conversation between board members of the Winter Park Chamber of Commerce. Debra Hendrickson, now vice president of the chamber, was an adamant supporter of the dialogue when it started back in 1991, when members felt a need to bring leaders together to network and learn from one another.
And after closing her ladies apparel business on Park Avenue and serving as CEO of Leadership Seminole for four years, Hendrickson missed Winter Park, and brought her history of enterprise full circle when she returned to Leadership Winter Park as a staff member of the chamber.
"It's an opportunity for business professionals to come together and make a difference in their community,” Hendrickson said. “We're building community trustees. The program itself is a community awareness program … you become connected to the community in a way that you haven't before.”
The return on investment for the program isn't the typical monetary break-even — participants leave with a host of new relationships, leadership skills and a newfound perspective about Winter Park's nuances. A selection committee chooses the top 45 applicants from the pool of potentials, which range from college graduates to retirees wanting to give back to their neighborhood.
Hendrickson recalled a class years ago in which a heated discussion took place about Hannibal Square's transformation and construction changes. A participant, who lived and grew up in the historical neighborhood, expressed his concern with the changes. Hendrickson said the debate was enlightening — none of the participants would have known about the man's treasured roots in the square had it not been for the discourse.
Shannon Rogner, current Leadership Winter Park student and executive director at Rollins Crummer School of Business, said she valued the experience of responding to a mock heart attack emergency when visiting the fire department during one of the sessions, and even helping with a car accident simulation in which participants had to smash open the window of a car as though to retrieve a person from inside. Being in the responders' shoes, Rogner said, helped her develop an appreciation and understanding for those who do these jobs on a daily basis.
"Now whenever I pass by one of these places, I have a new appreciation for what's inside and who's inside," she said.
Though nestled in the heart of Winter Park, the woodsy and charming Rollins College, Rogner said she hadn't been to many of the venues that her now close-knit leadership class has visited together, such as the Morse Museum. She's now driven to further her awareness of the community and call upon the connections she's made to be a resource for others, and ultimately be a better leader.
"When I get to interact with them individually … I get to learn a lot more about what goes about in the community," she said.
Freid said the most compelling aspect of the program is despite having a common goal of thriving as a leader, each individual who attends the class has something unique to offer.
“If I'm sitting here behind my desk then I'm not learning and I'm not growing — and that's not good for our business,” he said. “You never know who you're going to meet and what you're going to learn.”