The chapter discusses how career adaptability can be valuable in constructing sustainable careers. Still, the concept faces a number of challenges and unresolved issues. First, we address the conceptualization of career adaptability as a composite construct and argue in particular that the component of career exploration may be less beneficial but more problematic in terms of functioning and outcomes than previously assumed. Secondly, we propose additional dimensions and other influences on career development that could either explain previous inconclusive findings for career adaptability or that could be helpful beyond the agentic perspective dominantly applied in the literature on career adaptability. We argue that career adaptability functions differently for adults than for adolescents because of different career phases, investments and entrenchment, and because of the differing goals that people have in different life transitions. We also discuss uncontrollable influences such as social context, chance and chaos. After turning to the value that awareness can add to deliberate exploration, we try to strengthen the notion that some stressful career events and transitions may act as a blessing in disguise. To conclude, we give implications for practice and research.