Kris Kristofferson is in the Country Music Hall of Fame, but it took a while for him to launch his career. One big break was at age 29 when he was sweeping floors at a Nashville recording studio. He met superstar Johnny Cash, who was working there on an album. A few years later, Kristofferson boldly landed a helicopter in Cash’s yard to deliver his demo tape. That prompted Cash to get him a breakthrough gig at Newport Folk Festival. Further your goals with a similar sequence: luck to put you in the right place at the right time, followed by brazen yet charming acts of self-promotion.