From Transition to Triumph: Matt's Story

12/4/2025

When Matt graduated from Winston Transitions in 2016, he had no idea how quickly time would fly, or how much he would grow along the way. “It’s unbelievable how fast it’s gone,” he laughed during our recent catch-up. Nearly a decade later, Matt continues to embody the core values of perseverance, reliability, and pride in meaningful work that defined his time at Transitions.

Matt’s Journey from Transitions to Independence

After completing his program, Matt began working with Ken’s Crew, a nonprofit that partners with major retailers to create supported employment opportunities. Through that partnership, he secured a job at Home Depot, where he spent several years mastering skills in inventory management, truck unloading, and customer service. “It wasn’t just pushing carts,” he explained. “I worked on the loading dock, helped organize products, and talked with customers. It felt good to be part of a team.”

Matt’s hard work didn’t go unnoticed, he earned several awards and badges along the way, finishing strong as Employee of the Month in his final month at Home Depot.

Matt as “Employee of the Month” at Home Depot

After many years of success at Home Depot, and moving to Massachusetts, Matt transitioned to a new role at Wegmans, where he continues to thrive. He enjoys the steady pace, teamwork, and opportunity to help customers daily. “It’s close to home, and I really likethe people I work with,” he said with a smile. Reflecting on his time at Winston Transitions, Matt credits the program’s structure, guidance, and internship experiences for helping him prepare for life after school.

Matt interning at Cassin & Cassin LLP

Matt also emphasized how his daily Transitions commute from Connecticut to New York City played a major role in his personal growth. Navigating public transportation taught him independence and confidence, qualities that continue to serve him well as he now travels solo across the country to meet family for vacations.

Matt’s story is also one of connection and family. He remains close with his loved ones and treasures the time they share, whether relaxing at home or spending a day out on the water. “My family’s doing great,” he said proudly. “It’s nice getting to spend time with them.” Matt also keeps in touch with a longtime friend from Transitions, and the two still chat regularly.

Looking Ahead and Advice for Others

When asked what advice he’d offer to current and future Transitions students, Matt didn’t hesitate:

“Take time to be whomever you want to be in life, get the help, work hard, listen to your teachers, and don’t give up. It’s not always easy, but it’s worth it.”

Nearly ten years later, Matt’s journey continues to inspire. His steady progress, strong work ethic, and positive spirit are reminders that with the right support and perseverance, growth never stops, and every step

forward is a triumph.

Do you know someone who would benefit from the Transitions Program in New York or San Francisco?

Winston Transitions is an individualized day program for students ages 17 to 21+ with learning differences, who need more time prior to launching into higher education or the workforce. Transitions provides flexible programming tailored to each student’s learning profile, social-emotional needs, and future goals.

Want to learn more?

Contact John Civita, Director of Transitions Programming, at jcivita@winstonprep.edu or visit our website here

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Winston Preparatory School is a leading school for students with learning disabilities, including dyslexia, executive functioning difficulties (ADHD), and non-verbal learning disorders (NVLD).

WPS does not discriminate against applicants and students on the basis of race, color, national or ethnic origin. The Winston Preparatory School provides programs and services and equal opportunity in the administration of its educational and admissions policies, financial aid programs, employment, and the selection of its governing board without regard to gender, race, color, creed, religion, national origin, sexual orientation, disability status, or any status recognized by federal, state and local civil rights and non-discrimination laws.