Yogi Berra said a lot of stupid things that had a ring of truth about them, such as “Even the future ain’t what it used to be,” “You can observe a lot just by watching,” and “Half the lies they tell about me aren’t true.” Such sayings come to mind as I reflect on my 50-plus years of observing trends and issues in higher education, especially the last 46 years as a professor, dean, provost, and senior vice president at Converse College, a women’s college in South Carolina. What truth is there in what educational prophets predict? Educational prophets have not always seen the future clearly, of course, and I am no doubt among that myopic crowd of prognosticators. It is difficult to discern the uncertain future of single-gender colleges in the 21st century, but I hope that some of my observations are at least half-true. It is not always easy to know “where you are going.” First, a few observations on where single-gender institutions have been since Harvard College opened its doors to men in 1636.