Boys and Girls Club kept me out of prison. It kept me focused in school and on life; and has made me a productive citizen in the society. (Boys & Girls Club alum) This qualitative study evaluated and compared the influence of the Boys & Girls Club and Keystone Club programs on alumni in regards to their career and life experiences. Data were collected through personal interviews of each alumnus in the study. Each interview focused on the alumni’s experiences and benefits gained in either the six core areas of the Keystone Club program or the five core areas in which Boys & Girls Club members participate. The researcher asked staff from the Bryan and College Station Clubs to identify alumni for whom they still had contact information and would be likely to participate. The researcher then used the naturalistic inquiry approach to gather information regarding the experiences and benefits of alumni’s participation in the Keystone Club and Boys & Girls Club programs. The sample of convenience included 14 individuals who had participated in either program in the cities of Bryan or College Station, Texas. The major findings of the study were as follows: 1) All Boys & Girls Club alumni and Keystone Club alumni learned leadership skills through their participation in the programs; 2) All Boys & Girls Club alumni and Keystone Club alumni learned to interact with various cultures as a result of their exposure to the programs; 3) A greater number of alumni from the Keystone Club described “goal setting” as a key lesson than did alumni from the Boys & Girls Club; 4) Alumni from the Keystone Club are more likely than the alumni from the Boys & Girls Club to give back to their community. Recommendations for the clubs include the implementation of community service projects in the Boys & Girls Club program as well as helping youth identify and set goals. For the Keystone Club program, a Job Shadow Day and a College Student Shadow Day were both recommended to help students identify future careers and explore higher education.