In this episode, retired Army aviator Shawn Longwell shares his journey from Blackhawk crew chief to Apache pilot, then to leading Little Birds in the elite 160th SOAR before transitioning into civilian aviation. He talks about moving into Helicopter EMS, the challenges of single-pilot IFR flying, and how timing and persistence led him through JetBlue’s Rotor Transition Program to the airlines, where he now flies the A320/321. Shawn reflects on the lessons of adapting to new roles, balancing family in career decisions, and the importance of networking, timing, and humility in aviation transitions.