Most students expect that completing college applications will be a short-term effort, temporarily inconvenient to the rest of their schedule, but generally able to be subsumed within their daily lives. In reality, the challenge of opening one’s life to analysis, in order to write autobiographical essays required in applications can create an unexpected emotional response, which can extend throughout the college application season – roughly from October through January. In addition, concerns about being accepted or not, can create further stress, so editing each word in a college essays takes on “life-altering” proportions or thoughts that one wrong answer on the SAT can stymy any chance at future success. In ten years of advising students, not one has been immune to the emotional side of applying to college. While the emotions can be taxing, and add complexity to the college application process, the pains of applying to college can be character building in the long run, yet are not so enjoyable in the short run.