There’s an important life event happening halfway around the world that you don’t want to miss but you are stuck in indecisiveness. Should I go? Should I stay? Living abroad without regret is one of my core principles and knowing when to make a grand gesture is part of living that. Inspired by my decision to say “yes” to 42 hours of travel to spend nearly the same amount of time celebrating my parents’ 50th wedding anniversary, I share guidelines on what to consider when contemplating whether it’s time to make a grand gesture.