Growing up, Sky presented himself as a tomboy, though in high school, he tried to change and fit in with the girls, which he said felt fake and uncomfortable. Soon, he started hanging out with his high school's lesbian crowd, cutting his hair and wearing baggy clothes, and playing in a punk rock band. This still was not the right fit for him. It wasn't until meeting a trans woman at a concert when he was 15 that Kergil realized who he was (or wasn't). Over the next several years, Kergil met with a gender therapist and started going by the more gender-neutral name Skye. He came out to his parents as a transgender man, and though greeted initially by concern, he was soon met with immense support from them. He started testosterone in early 2009, his senior year of high school. The timing was important for him since he wanted to start at Skidmore College presenting as a man.