Windsor embarked on a two-year teacher training program in Bangor, laying the groundwork for a career in education. Following the completion of his training, he ventured into the world of teaching, taking on roles in History and English at a school located in the vibrant Elephant and Castle neighborhood of London. It was during this time that he crossed paths with Lynne, a dedicated nurse, at the Welsh Club. The couple's chance encounter blossomed into a romance, and by the time Windsor reached the age of 32, they had welcomed two children into their family and were residing in the picturesque town of Leek, situated in the heart of Staffordshire.
Despite his initial passion for teaching, Windsor's creative inclinations eventually led him to explore the world of amateur dramatics. It was Lynne who encouraged him to take the leap and pursue his theatrical aspirations. The casting director of the esteemed Royal Court Theatre took notice of Windsor's talents and offered him a spot in the Cheltenham Reportary production, which marked the beginning of his journey in the show business industry. This career-defining opportunity, which paid a modest £10 per week, served as a springboard for Windsor's future success in the entertainment world.
