The present study aimed to extend understanding about the relationship between career adaptability, courage, and life satisfaction in a sample of Italian adolescents. It was hypothesized that courage partially mediated the relationship between career adaptability and life satisfaction. Specifically, 1202 Italian high school students with an age from 14 to 20 years (M = 16.87; SD = 1.47), of which 600 (49.9%) boys and 602 (50.1%) girls, were involved. Using a multigroup approach across gender, it was found that courage partially mediated the relationship between career adaptability and life satisfaction in boys and girls. Results suggested the relevance of career interventions to promote career adaptability and courage for strengthening life satisfaction in adolescence.Western European societies are characterized by fast modification of work environments, rapid technological changes, economic and social insecurity and instability, unemployment, due notably to the worldwide financial crisis, globalization, and migration flows. As a result of these social phenomena, adolescents tend to perceive their future to be full of risks (Schoon, 2007), and thoughts about the future constitute one of the main fears and concerns among other domains (e.g., relationships with parents and peers). Adolescents can experience anxiety and distress about the future, that might affect their psychological health and their levels of life satisfaction, so that Lange (2013) highlighted that job insecurity, as the perceived risk or fear of future unemployment, has a detrimental impact on personal well-being. This perception may occur especially among adolescents in countries such as Italy, where the rate of youth unemployment and precariousness is higher than other EU countries (EUROSTAT, 2016).The Life Design, developed primarily to help individuals to construct their career life in the current changing societies, is a paradigm for career counseling based on the epistemology of social constructivism and considers career development as the result of a dynamic interaction of person and environment. It stimulates persons to reflexively imagine and construct a life arranged with viable and multiple roles to guarantee well-being and adaptive functioning (Savickas, 2015). Central to the life design paradigm is the concept of career adaptability, that is an essential resource to help individuals plan their uncertain future, face adverse working conditions, adapt to changes of the job market and job conditions, and therefore increase their well-being (Savickas, 2015). In this current socio-economic context, particular relevance is also given to the propensity of individuals to behave courageously and persist despite perceived risks (behavioral courage), as this resource seem to be a strength when making difficult career choices despite fears