Retirement isn’t a single event, but a process that varies in when it happens and how long it takes before the person adjusts to a new way of life. Planning for retirement should include developing financial literacy at the start of a career so earnings and savings are smartly invested; preparing for the time by figuring out how to structure newfound freedom; not stopping all work abruptly but providing for some period of transition; beginning to take on more activities that one prefers to do rather than what one has to do; and giving some thought to facilitating a smooth relationship with successors. Both those letting go and those coming on occupy different psychological and generational space, and their differences in perspective are normal. One’s perspective is no more right than the other’s, but they are viewing matters through different lenses, setting the stage for potential misunderstandings.