Trina McCaskill’s journey has been anything but easy. Her path, though long and at times lonely, has been a blessed one, shaped by resilience, perseverance, and an unwavering commitment to growth. Identifying as a true survivor, Trina has transformed her struggles into stepping stones, using lessons from her past to shape a purposeful future.

Growing up in a large family, Trina often felt like the black sheep, facing challenges that tested her self-worth and direction. Some early decisions led to encounters with the law, unhealthy relationships, and environments that hindered her potential. At 19, she became a single mother, opening a new chapter filled with both responsibility and determination. Balancing the demands of motherhood, education, and societal expectations left her feeling lost and overwhelmed. A marriage that ended in divorce further tested her strength, as she battled depression and learned the importance of self-love and valuing her worth.

Determined to create a better future for herself and her children, Trina became self-sufficient and ventured into entrepreneurship. She first opened a daycare center but, recognizing it was not emotionally or financially fulfilling, shifted her focus. Returning to school at Sojourner-Douglass College, she earned a certification in phlebotomy and discovered her passion for helping others. This led her to pursue additional certifications, including Med Tech licensing from the State of Maryland, enabling her to open McCaskill’s Assisted Living Facility, which she continues to own and operate successfully.

Driven by a desire to serve beyond her business, Trina founded Turning Lives Transitional Inc., a program dedicated to supporting men and women reentering society. The organization provides life skills, training, and resources to help participants live independently and confidently. Her commitment to service also led her to become a Psychiatric Rehabilitation Program (PRP) counselor, assisting clients in overcoming challenges such as depression, substance abuse, and educational barriers while developing essential life skills.

In addition, Trina serves on the Board of Executive Directors for People Empowered by the Struggle, under the leadership of Founder and CEO Yolanda Pulley, who instilled in her the principle: “In order to understand the people, you have to be one of the people.”

Today, Trina proudly declares that she has become bigger than her greatest mistake. She walks in victory, no longer powerless, and is dedicated to empowering others to recognize their own strength. Known as a “warrior in struggle,” she embodies resilience and inspires others to rise above adversity.