Flexibility is considered one of the key resources for a successful adaptation to the world of work. It has also been defined as "the positive side" of career reconsideration process in vocational identity theory. However, previous empirical observations conducted in the Italian context have highlighted the negative relationship between vocational identity flexibility and psychological resources in adolescence. The aim of this study was to examine the relationship between vocational reconsideration dimensions and positive and negative outcomes of psychosocial functioning in a sample of Italian high school students. Structural equation modeling was performed in order to test theoretical hypothesis about the relations between reconsideration dimensions, agency, well-being, internalizing symptoms and externalizing behavior. Results confirmed a general association between vocational identity flexibility and negative psychosocial functioning. The study shows how a better conceptualization of career reconsideration dimensions is needed. Finally, the results warn against an excessive promotion of vocational flexibility among adolescents and encourage high schools to support students in their life design process.