The One Decision That Could Have Changed Everything I remember my first work trip like it was yesterday. It was 1999, and Progressive Insurance sent me to Hawaii for 10 days as a reward. Hawaii. For work. I thought I had died and gone to heaven. I flew out on January 31, landed in paradise, and rented a Mustang from Hertz. Solo business travel never felt so good. The ocean breeze, the freedom, the sense that life had just cracked open in front of me. Then, things took a turn.