The current study examined how adolescent personality contributes to the development of frugality and perseverance. In addition, the study examined how frugality and perseverance promote parental involvement and school engagement in adolescence. Participants were taken from waves 3, 4, and 5 of the Flourishing Families Project and included 341 two-parent families with at least one adolescent between the ages of 12-15 at Wave 3 (mean age = 13.28, SD = 1.01, 48.4% female), 92.6% of whom had complete data for Wave 4 (1 year later). The first major finding revealed that adolescent conscientiousness, agreeableness, and emotional stability predicted frugality and perseverance via structural equation modeling. The second major finding was that parental involvement promoted adolescent school engagement. The current study helps to better understand the interplay between adolescent personality, frugality, perseverance, parental involvement, and school engagement.