Jake Picking was born in Germany, where his father, a member of the United States Army from West Point, was stationed (though some claim he was born in Massachusetts). He grew up in Wellesley, Massachusetts. At New York University, Picking was a winger on the New York ice hockey team. He dropped out of business school after a year because he was more interested in acting and student film projects. As an ice hockey player, Picking appeared in an NHL commercial before his acting career.
Picking's high school math teacher encouraged him to try out acting, and he took lessons with Carolyn Pickman, a casting agent who also represented Ben Affleck and Matt Damon.
Picking finally began attending auditions in Boston, in 2013 he made his feature film debut with a role in the youth film The Way, Way Back with Steve Carell. This was followed by guest appearances in the series Ironside (2013) and Chasing Life (2014). To start a professional acting career, he moved to Los Angeles, where he initially studied old Hollywood films with stars such as James Dean, Paul Newman, Marlon Brando or Montgomery Clift in his one-room apartment out of loneliness. He preferred moving to the West Coast to a possible acting course at the NYU Tisch School of the Arts, although he had no contacts whatsoever in Los Angeles.

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