A listener wrote into the Bobby Bones Show's Anonymous Inbox asking what moment in his career made him realize he had “made it.”
Bobby admitted the “therapy answer” is that he still does not really feel that way, but two moments immediately came to mind. The first was buying his mom a trailer and two acres of land. Bobby said that moment felt like he was “breaking generational difficulties.” He also recalled buying his first pair of Jordans after growing up wearing shoes bought at yard sales. Bobby kept the shoe box for 15 years, even after the shoes wore out from use. Those two moments stand out more than any career accomplishment. He said awards and milestones like being the youngest person inducted into the Radio Hall of Fame, winning Dancing with the Stars, and having The New York Times bestsellers are all “really cool,” but they were not the first things that came to mind.
Amy then shared her own experiences. The first moment she thought about was when Bobby surprised her with George Strait. Amy explained that Bobby had told her she was doing a phone interview with George Strait, only for the singer to walk down the hallway while still on the phone with her. George Strait played along with the prank and eventually walked into the studio. She recalled thinking, “Wait, this is what I get to do? This is part of my job?” Amy also reflected on winning a Gracie Awards award in Los Angeles with both of her parents present. She said the recognition stemmed from the show’s work packing hunger relief meals for Haiti through “30 Abes.” Adding that being part of a show that can bring listeners together to make an impact is one of the most rewarding parts of her career.