Although managers and professionals still compete in a career tournament for advancement and pay, the career boundaries that they cross in order to compete have changed. Traditionally, such individuals came up through the ranks within the same company by specializing in one functional area and changing, as needed, the geographic location of work in order to advance their careers. However, in the current era of less constrained, boundary-crossing careers, they are more apt to cross several boundaries, including functional, organizational, geographic, and family, as they pursue career opportunities. Using survival analysis with data from the career histories of 760 managers and professionals who collectively made 3917 moves up to midcareer, we examined the impact of the rate of crossing each boundary on the subsequent likelihood of advancement. In addition, over this span of career, we examined the extent to which more rapid advancement contributed to the rate of growth in annual salary. Our findings suggest that crossing functional, organizational, and geographic boundaries more often significantly increased the likelihood of advancement, whereas the duration of family boundary crossings had a negative impact. Moreover, as expected, advancement had a long-term impact on salary growth. (Contains 3 tables.)