In an effort to prepare American high school students for future careers, many states have implemented specific career readiness standards and programs. One such program is known as Extended Learning Opportunities (ELO), which are hands-on, credit-bearing experiences outside of the classroom with an emphasis on community-based career exploration. While there have been a handful of established career readiness programs in Maine high schools for over a decade, the state recently implemented the Maine Career Exploration Program in 2021 to build infrastructure to support statewide ELO expansion in the long term. Utilizing a phenomenological analysis approach, this qualitative study examined the efficacy of ELO programming to determine specific benefits to alumni and to examine how it has affected their future career decisions and outcomes five to ten years after graduation. In this study, public high school graduates who earned credit through an ELO shared their experiences through structured personal interviews. Participants graduated from one of three high schools in southern Maine which have all had existing ELO programming for at least ten years. Using Krumboltz's (1976, 1979, 1996) Social Learning Theory of Career Decision Making and Learning Theory of Career Counseling, this study aims to fill the current knowledge gap regarding ELO effectiveness and benefit to alumni and the ways in which it impacts future career choices. Given the current investment of implementing ELO programs in Maine, such effects should be studied and understood. Findings suggest the essence of ELO experiences are overwhelmingly positive, advantageous, and effective. Other findings show ELOs create important connections, provide early immersion in the professional realm, give exposure to new perspectives, increase confidence, and support autonomy over one's learning and future. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]