A middle-class Roman Catholic Italian, hockey player, avid drummer, and popular kid, Monica Miatello (formerly Chris) knew she was different from the age of five. But it was the late 1960s—a time when information about gender dysphoria was practically non-existent. As a result, although she had many friends, her childhood and teenage years felt lonely and isolating. That is, until she met Sandy. Falling in love and getting married weren’t things Miatello ever thought would happen to someone like her. Both pharmacists, the couple moved to a small Ontario town of 900 people, purchased a pharmacy, and had two daughters. With Sandy’s support, Miatello navigated the hills and valleys of her secret cross-dressing life, which ultimately led to her transition in the late 1990s. Her courageous journey from life as a man to embracing life as a woman couldn’t have happened without transparency, honesty, and a patient willingness to educate those around her. It also required the support of people who accepted her authentic self, an openness to discovery, and the ability to trust others. And it would not have happened without humour, positivity, and the ability to laugh at—and love—herself. Heartwarming, emotional, and empowering, Erasing The Five O’Clock Shadow is a remarkable and inspiring personal story about transitioning and being transgender in an ever-changing world.