Judy McCutcheon’s journey is an awe-inspiring testament to the power of determination and the unwavering pursuit of a better life. Born and raised in the vibrant tropical paradise of Trinidad and Tobago, renowned for its carnival and soca music, Judy emerged from a large family of ten siblings as the eighth child. In their humble settlement in Tobago, where material scarcity was a constant companion, Judy’s upbringing was not defined by abundance but by the unbreakable bonds she forged with her siblings.
While Judy’s childhood was marked by moments of hardship, such as days when there was no food on the table or the times she walked to school without shoes, she refused to let her circumstances dictate her future. Instead, she found solace and strength in the camaraderie and love she shared with her brothers and sisters. This unyielding spirit ignited a fire within her—a burning desire to rise above her circumstances and create a life of purpose and fulfillment.
A turning point arrived when Judy’s mother, driven by foresight and sacrifice, made the courageous decision to send young Judy to a private school—a privilege that her seven older siblings had never experienced, as they attended government schools. This opportunity opened doors to new possibilities and transformed Judy’s perspective on her own identity and aspirations. At St. Joseph’s Convent, she was exposed to a world that stretched beyond the confines of her humble beginnings, igniting a flame of ambition within her.
At the age of 17, Judy caught a glimpse of the life she had dreamed of when she temporarily resided with one of her teachers and her husband, a chief engineer with the government at that time. The stark contrast between her previous living conditions and the comfort of her own room and bathroom left an indelible mark on her spirit. Fueled by these experiences and armed with raised expectations for a better future, Judy made a bold decision at the age of 19—she would move to Trinidad, guided by unwavering faith that success would follow.
In her quest for a better life, Judy took on various odd jobs, each one a stepping stone toward her dreams. And then, fate intervened, bringing Hasely Crawford into her life—a figure who would prove to be instrumental in her journey. Through their meeting, Judy found not only a friend but also a guiding light who believed in her potential and encouraged her to unleash her untapped abilities.
Recalling her encounter with Hasely, she says, “I remember telling him that I needed a job, and without hesitation, he asked me to send him my resume. He knew someone who might be a perfect fit. I sent him the resume, and true to his word, he forwarded it to his contact.”
Judy grew up in a Christian home, a common characteristic of Caribbean households. Although individuals may stray, the foundation always remains and so the Monday after her conversation with Hasely, she offered a specific prayer, saying, “God, by Friday, nine o’clock, something has to happen.” Alone in her house, the phone rang precisely at nine o’clock. She answered, and a woman on the other end asked for her using her full name at the time, Judy Mahalia Jack. She explained about receiving her resume from Hasely. She was invited for an interview and subsequently landed the job as an Accounts Payable clerk at Prestige Holdings, the offices for Kentucky Fried Chicken.
When asked about the aspects she loves about being a black Caribbean woman, Judy emphasizes the freedom to be herself. Growing up in the Caribbean, she always experienced a particular level of freedom to express her true self without reservation. She acknowledges that remnants of slavery still impact interactions among Caribbean people, and some women struggle to fully express themselves. However, she has never experienced such limitations. Boldness has been a defining trait instilled in her since childhood. Her sister used to tell her, “You are bold,” and she has always embraced it—asking for what she wants, and expressing her feelings, all while respecting others. Even if she received a low conduct grade in school for speaking her mind, she didn’t mind. Being true to herself was more important.
Two years into the marriage and I realized that I couldn’t continue in the relationship. I had grown and desired more than just the party scene we were immersed in. I wanted something deeper, while my husband was content with the lifestyle we had. As issues of infidelity arose, including someone getting pregnant, I knew that it was time to end the marriage. I initiated the divorce and even paid for it myself.
I remember the resistance I faced from my ex-husband when it came to signing the divorce papers. I called him and made it clear that I wasn’t asking for anything except the end of our marriage. If he refused to sign the papers, I threatened to take everything he had, including his shirt. Faced with that choice, he finally signed the divorce papers that same afternoon.
Read More Of Judy’s Story On Page 31 of our latest Issue (Issue 17)
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