Second acts rarely begin with a clean slate. More often, they grow from honest reflection and a desire to build something better than what came before. In business and life, leaders who have the strongest second acts are the ones who confront the past and move forward with intention.
Few people embody that kind of reinvention more than Jayson Williams.
Many remember Jayson for his years at St. John’s and his rise to NBA stardom. Fans admired his energy, his talent for elevating his teammates, and his relentless approach to the game. When his career on the court came to a close, he entered a period that tested every part of his identity: Addiction, legal trouble, and time in prison unfolded in full public view.
It would have been easy—and understandable—for that chapter to define him, but he didn’t allow it to.
A New Direction Built on Hard Lessons
I recently had the opportunity to sit down with Jayson and was struck by how honestly he talks about his past. He doesn’t sugarcoat anything. He studies it, learns from it, and treats it as the foundation for his next chapter. That clarity has shaped the incredible chapter that followed.
Watch my conversation with Jayson:
When he retired from basketball, Jayson expected to ease into a quieter life. Instead, the silence left him unfocused and vulnerable. As he puts it, “When I lose focus, and I get idle, self-destruction comes upon me.”
Drinking took hold, and the people who cared about him—Curtis Martin, Chris Mullin, Charles Oakley—showed up at his home and told him he needed help. He went to treatment in Florida, but the experience left him feeling disconnected. When he returned home, his friends insisted he continue, but this time, they challenged him: If the program doesn’t work for you, build one that does.
That was the spark.
Jayson realized that if treatment was going to hold his attention and match the way he was wired, it needed movement, challenge, and purpose. He returned to Florida and created REBOUND, a recovery and reentry program grounded in physical engagement.
“I created it for me,” he told me. “If I’m having fun doing it, and I can make it efficient and put my passion into it, it can overflow… and go on to everyone who works with us.”
REBOUND incorporates outdoor experiences like paddleboarding, snorkeling, skydiving, and fishing. Achieving something difficult, especially as part of a team, helps people see themselves differently.
REBOUND on the Road: A Whole-Person Approach
Jayson’s newest effort, REBOUND on the Road, adds a career pathway to the program. Participants earn commercial truck-driving licenses, but the training is only one part of the story, as it focuses on developing the whole individual.
Participants spend their days together from early morning to evening. They share breakfast, attend classes, and work out together. They gather for prayer and reflection while also studying as a group, supporting one another through every challenge. By the time they reach the driving portion of the program, they’re as much a family as they are trainees.
And unlike the quick, transactional CDL programs that push students through in a matter of weeks, REBOUND on the Road is designed as a comprehensive 90-day journey that builds confidence and character.
For Williams, this work has deep roots. His earliest memories involve riding alongside his father in a tractor-trailer, hauling equipment across the region. Those experiences shaped his work ethic and his belief that truck driving can offer someone a stable future.
Leadership in the Open
There is a leadership lesson in how Jayson is building his story. He openly discusses the mistakes he made and the people he hurt, which can inspire trust and show that honesty builds strength. That kind of openness is rare. Many face difficult chapters, and the instinct is to conceal them. Jayson demonstrates that honesty about struggles can become a source of strength.
Every leader faces setbacks-failed strategies, shifting markets, or team struggles. The true test is how you respond. A strong second act involves humility and a focus on serving others, which can motivate readers to lead with purpose and resilience.
Williams’ journey reminds us that second acts are built gradually, step by step. They require honesty and the continuous decision to keep moving forward.
Williams chose to transform that experience into something that lifts others. His life today is a testament to what becomes possible when someone commits to growth and uses it to help people find their own footing. In a world that moves quickly, consider: What challenges in your life could serve as a foundation for your own reinvention? His example reminds us that reinvention is always within reach if we are willing to reflect and act.