Advocating a holistic approach, the life design paradigm suggests that individual and environmental constraints as well as resources shape people’s career journeys and their broader evolution. In particular, career adaptability and career resilience are central personal resources that help people in designing their career. In specific situations, people are able to activate these resources, and career interventions can strengthen them. Career adaptability and career resilience also help people to better use their environment’s resources, which eventually contribute to their employability. Over time, these constant interactions between people and their environment can lead to the development of negative spirals or virtuous circles, ultimately fostering adaptive functioning, and a successful life. People’s career path and employability thus depend on a combination of personal, and environmental factors, occurring within specific organizational, social, economic, and political structures.