Travel back in time with me, if you will, to 1999. College admissions had recently transitioned from a buyer’s market to a seller’s, and application totals at many colleges began the steady climb to what continue to be unprecedented numbers. Twenty years ago marked my foray from college admission into college counseling as well. I have been on the front lines with students and parents through three different iterations of the format of the SAT, the evolution of web-based college searching, and the transition from paper to online applications, including the expanding reach of multiple online application platforms. 1999 was not just the beginning of my career in college counseling, but of an ongoing commitment to help students keep their wits about them in what, for many, is an overwhelming process. This includes helping them to be strategic about their college lists.