According to the Career Construction Model of Adaptation, career decision-making difficulties (CDD) and life satisfaction are important adaptation results, and career adaptability is a crucial resource to attain positive adaptation results. This study focused on the influence of parental career-related behaviors on career adaptability, CDD and life satisfaction, and the mediating role of career adaptability between parental career-related behaviors and CDD and life satisfaction. Five hundred thirteen Italian students (182 of middle school, 141 of high school, and 190 of university) were involved. The results showed that parental support influences CDD and life satisfaction both directly and indirectly through the mediation of career adaptability. Parental interference and lack of engagement have a positive direct effect on CDD. Finally, CDD and life satisfaction are significantly and negatively associated. The data support the key role of parental support and career adaptability in CDD and life satisfaction. Practical implications are discussed.