New College students have created SailFuture, a nonprofit mentoring program for at-risk high school students.

Navigating Life

As the sun sets over Sarasota Bay, four sailboats dart upwind and downwind, tacking and jibing, maneuvering around buoys in a graceful, looping chase.

Aboard them are two-person teams, one a student from Sarasota’s Booker High School, the other a mentor from New College or the community. They are the third class of SailFuture, a nonprofit program created by fourth-year public policy student Michael Long and run entirely by New College students.

Sail Future is about second chances. The program pairs high school students who have serious academic or discipline problems with mentors close enough in age to be able to relate to them. They team up on homework, on trust and dialogue exercises, and most importantly on the sailboat: One key aspect is that both the student and the mentor are novice sailors, making them equal partners in the lessons. The boat, and the lure of wind and water, is the key, Long explains. “These students would never buy into a traditional mentoring program,” he said.

But it’s more than just the reward; sailing offers lessons, metaphors for life. Every day on the water is linked to an idea, like teamwork, perseverance, and confidence. On this evening, the lesson was to be at the line when the whistle blows. In a sailing race, a boat that’s off the line is at a severe disadvantage. In school, those at the starting line are the class valedictorian and the A students, Long said – something the students already know too well.

But they wanted to prove a more important lesson, so Long and partner Cornell “CJ” Lee, the program’s sailing director, started hundreds of yards off the line, far behind the students. With their skill and experience, they soon shoot past the other boats. That sent their message: “You can start way behind the line, and you can still catch up and pass everyone,” Long said.

The day, as usual, began in the Environmental Studies classroom. It has to be torture for the students – they’re less than 100 yards from the sparkling bay and the sailboats – but there’s no complaining. Lawrence, a burly guy with dreadlocks, is working with second-year student Garrett Murto on a report on the Great Depression. They talk out the meaning of stock speculation; Lawrence deduces it’s essentially guesswork on the future price of a stock, and what happens when those guesses are wrong.

Brandon is working on a physics lab with first-year student Alex Witter, measuring the speed of falling bodies. Tia is doing a math word problem, figuring the size of a house’s wall from the dimensions of its roof, with some guidance from a mix of mentors. Willie is procrastinating, saying the remaining homework time isn’t enough for a long online application he needs to do. Long prods him to manage his time and do some of it now.

Outside, Lee, a third-year student aiming for medical school, is planning the day’s lesson. A native of sailing capital Annapolis, Md., he learned the art from legendary yachtsman Stuart Walker. Four weeks in, the skills are still basic, but that’s not the point. “This isn’t designed to teach them to sail as fast as possible,” he said. “It’s about teaching them life lessons and the sailing is part of that.”

Sometimes the biggest lessons, and the biggest payoffs, happen off the water. As the boats raced, Aaron, a slender, thoughtful young man they call “the philosopher,” stood on the beach and watched. Last week, he had received a concussion in a fight in school and was not yet cleared to be back on the water. “Sailing’s not the easiest thing,” he said. “It’s meant to challenge us. It teaches you that life is not going to give you leeway. It’s not going to go easy on you. SailFuture is people actually serving other people, giving that kind of push, that motivation.”

The other SailFuture students heard about Aaron’s injuries and started sending texts and Facebook posts supporting him. Then they gathered over the weekend; while one student took him out, the others set up a surprise birthday party for him. Later that night, Long told the same story. “They were like a family,” he said. “They were creating this support system, showing them that somebody cares.”

Hours earlier, watching his friends on the water, Aaron had the same thoughts. “He always says we’re a family,” he said. “It really says something about the program.”