After his appearance on Idol, Woolf deferred for one year an offer of admissions to Berklee College of Music until fall 2015. Woolf performed nationally in the American Idol season 13 tour, then held a 'Welcome Home' concert in Bradenton, Florida at IMG Academy Stadium on September 27, 2014. He opened a similar homecoming concert for his fellow American Idol season 13 finalist, Alex Preston, at the Capitol Center For the Arts in Concord, New Hampshire on November 8, 2014, and on February 28, 2015, he performed in Lakewood Ranch, Florida's Winterfest, along with The Doobie Brothers, War, Jefferson Starship, Matt Walden and performers from the Del Couch Music Education Foundation.
Woolf wrote and recorded a five-song EP, Pretend, which he self-released on December 18, 2014. The album was funded in part by crowdfunding, and was produced by Danny Blume who co-wrote some of the songs with Woolf.