The purpose of this study was to gain an understanding of the phenomenon of sport specialization through the vantage points of participants and the parents of participants. Research questions were related to motivating factors, academic performance, and emotional well-being for the specialized athlete. Participants that passed a screening survey that indicated background knowledge on sport specialization, where they or their child only participated in one sport throughout high school, were chosen for the study. A series of semi-structured interviews took place with participants and parents of participants to acquire a deeper knowledge on the dealings with the sport specialization experience. Some developing themes evolved in the study, which included an endearment of sport, relationships matter, autonomy and independence, handling discomfort and pain, and transitional skills through academics and sports. Further sub-themes were identified in the study--satisfaction, friends and teammate dynamics, coaching dynamics, immediate family and travel team influence, personal identity, aiming for success, injuries, surgeries, exertion, academic endeavors, and balancing responsibilities. Conclusions from the study were understanding motivation, academic outlook for the specialized athlete, and well-being outlook. Implications comprised of understanding the role of the specialized athlete, role for school leaders, role for parents, and role for sports directors. [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.]