In high school, Power was active in the theatre, playing Felix in the publicly staged production of The Odd Couple in association with TVO. He was a recipient of a Sears Ontario Drama Festival Award for directing and acting in the two hander Babel Rap by John Lazarus, while simultaneously directing a performance art piece ‘Journey’ by fellow student Ian Rye. The next year Power's improv troupe competed in the regional finals of the Canadian Improv Games in Ottawa, where they came second. During this time, Power was a member of the Young Actors Performance Troupe that performed in community centers and nursing homes a variety of vaudevillian cabarets and contemporary youth plays.