Goodwill of Central & Southern Indiana Blog

A Journey of Second Chances

Written by Jennifer Neer | May 5, 2026 3:24:36 PM

Montez Day knows firsthand that a single moment does not define a lifetime. Today, he serves as the Manager of Goodwill New Beginnings at Goodwill of Central & Southern Indiana, a role he stepped into in 2025 after starting as a facilitator and receiving several promotions since joining the organization in September 2021. But his path to leadership was shaped by years of transformation, education, and an unwavering belief in the power of second chances.

In 1999, Montez was convicted of bank robbery and sentenced to 24 years in prison. He ultimately served 20 years and six months. During that time, he made a deliberate decision to change the direction of his life. While incarcerated, Montez immersed himself in education and service. After being transferred to Terre Haute in 2005, he participated in college courses taught by Indiana State University professors who came directly into the prison, classes that continued even during prison lockdowns. Through that opportunity, Montez earned an associate degree in Human Interaction with a minor in Social Behavior.

Education became more than coursework; it became a purpose. Montez taught African American History and Psychology once a week for eight years and earned a Peer Forensic Specialist Certification from the U.S. Department of Labor. His goal was clear: to leave prison, continue his education, earn a master’s degree, and become a clinical psychologist. Though life ultimately led him down a different professional path, his mission remained the same: to help people rebuild their lives.

After being incarcerated for 20 years, Montez was interviewed by Dr. Trelles Evans, Director of Mission Coaching and Reentry Services at Goodwill, for entry into Goodwill New Beginnings. At the time, he had already completed similar programming in prison, and both parties thought the program would not benefit him. Two years later, after his release, a friend mentioned a job opening at Goodwill. Montez applied, was hired, and only then realized the connection: the program he now manages was the very one Dr. Trelles had once introduced to him.

Today, Montez leads Goodwill New Beginnings with authenticity and intention. He meets daily with community partners, builds critical relationships, collaborates with his leadership team, and supervises four staff members. He also serves on the board of Storytelling Arts of Indiana, continuing his commitment to amplifying voices that are often unheard.

What makes him most proud is the evolution of the program itself. “Being able to work with someone at the beginning,” Montez says, “and then watching them jump into a career, that’s everything.”

“Montez is someone whose lived experience shows that when you put in the work and have determination, you can change your life,” says Dr. Evans. “He has become a positive role model and is passionate about giving back to help others.”

Goodwill New Beginnings doesn’t just talk about second chances, it lives them. Goodwill offers employment opportunities to individuals with criminal backgrounds, based on their circumstances. Goodwill New Beginnings helps returning citizens successfully reenter society. Montez Day is proof of what’s possible when an organization truly practices what it preaches: belief, opportunity, and the courage to begin again.

If you or someone you love is returning to the community after incarceration, you don’t have to do it alone. Goodwill’s New Beginnings program is here to help you take the next step with support, training, and real opportunities. For more information or to refer a potential candidate, please contact the Goodwill New Beginnings office at 317-524-3956 or newbeginnings@goodwillindy.org.