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This study aimed to find how IT-related hobbies and interests impacted students’ educational and career decision-making. Methods: As part of a six-year-long, ATE-funded study of IT students at Ivy Tech Community College, our team conducted semi-structured, phenomenological interviews. These interviews were analyzed using keyword searches and a combined inductive-deductive approach to coding to explore how IT-related hobbies and interests interacted with other personal characteristics to inform student decision-making. Findings: Our team identified a potential link between early IT interest, IT-related hobbies, and persistence in IT education and careers. Many participants in the study had a moment of clarity where they realized that their IT hobby could become their career, the “hobby-to-career reckoning.” Contributions: This piece explores the potential connection between IT interests/hobbies and student outcomes within the field of IT while exploring the different social factors that may impact student decision-making and the role of the hobby-to-career reckoning in the decision-making process. This piece will give practitioners and researchers insight into how early interest in IT and IT-related hobbies may impact student decision-making about IT educational programs and careers.