The purpose of this multiple case study was to develop an understanding of what older nontraditional undergraduate English majors voiced as the challenges, attributes, and promises concerning their choice of that academic major. Ten participants took part in this study; these were students enrolled during the Spring 2012 semester as English majors at an urban state university in the Midwest. Data from ten interviews were analyzed using a combination of structural and verses coding. Thirteen themes surfaced that cut across cases and questions and offered insight and explanation to the research question and sub questions. These included (in alphabetical order): being older, coping strategies, encouragement, fear, finances, interruptions to enrollment, possibilities, reading's influence, resistance, skills gained, understanding the world, the English major's worth, and writing's influence. While these participants voiced challenges such as being older, fear, and interruptions to enrollment, in all but one case, the life-long love of reading and/or writing sustained their aspirations in the major. All participants envisioned careers that would utilize the skills gained in the study of the English major. All participants also stated that understanding the world better was a benefit of the English major. However, the encouragement to pursue the English major that participants received, whether the source of that encouragement was internal or external, took place in formal or informal settings, or was mostly positive or negative, permeated their entire lives. These participants swam in a sea of mostly positive encouragement that reinforced their choice of an English major. In some cases, these positive encouragements were nothing more than simple courtesies or compliments professors bestowed upon participants. While seemingly minor, these actions had a profound effect on students. Implications and future research are discussed. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]