Structured interviews with twenty women who are top corporate executives or entrepreneurs in the hospitality industry revealed the talent, resourcefulness, and support required to achieve such a position. During the interviews, these successful women cited these three keys to career advancement: (1) the importance of taking thoughtful risks, including non-linear assignments; (2) the criticality of networking; and (3) the significance of finding a sponsor. Two notable challenges for these executives were the possibility that they would be regarded as a token and the need to integrate their work and family life. They noted that keys to meeting work and family responsibilities were having flexibility and autonomy in their schedules and engaging a strong support network, which usually included a life partner. Eight of the twenty had stepped away from corporate roles to run their own businesses. These entrepreneurs acknowledged the considerable work responsibilities resulting from their choice; however, gaining control of their careers made the effort worthwhile and the experience meaningful.