NBA Superstar Dirk Nowitzki was unsure whether the 2018-19 season would be his last as an NBA player. He had not faced such uncertainty since 1998, when he had navigated a difficult decision regarding the timing of his move to the NBA. He also did not know what he would do when he ultimately retired, as playing basketball was all he had known for his entire adult life. His foundation in Dallas and in Germany provided grant money and strategic support to youth programs; he could become more directly involved in the foundation's work. The Dallas Mavericks had made it clear that they would be open to Nowitzki transitioning to a role as some type of executive or coach, helping the Mavericks make decisions and/or develop their young players. Nowitzki was also intrigued by the idea of becoming an independent mentor for young, amateur players; after all, his mentor, Holger Geschwindner, had been instrumental in his development, and he liked working with young people. Keeping his various options in mind, how should Nowitzki plan for the next phase of his life and career?