In 2009, Reagan joined Teach For America, taking him to the Rosebud Reservation in South Dakota to teach sophomore English at Todd County High School. He also coached quiz bowl, speech and debate and revamped the theater program, taking his students to win Superior Play at the South Dakota State One-Act Play competition for the first time in history.
In 2011, Reagan left the prairie of South Dakota to join the Stelos Alliance where he directs marketing efforts and co-facilitates the Housley Principled Leadership Program with Bill Poston. He also plays the role of Raconteur at the innovation consulting firm, Kalypso, where he helps discover new ways of telling Kalypso’s story to their global client base.
Reagan speaks regularly to student groups about leadership, branding and individual ownership. He has established regular literature and storytelling circles in several cities and publishes his poetry and creative writing on reaganpugh.com.