Globalized labor markets confront many adults, both employed and unemployed, with demands arising from career uncertainty that have the potential to jeopardize their occupational planning. This article investigated how individuals in different regions of Germany, which are characterized by different economic opportunities, negotiate such demands to pursue a career. The central hypothesis is that under unfavorable economic conditions, disengagement from demands of career planning, in terms of reducing commitment to their mastery, will predict positive changes in subjective well-being. This was tested using a sample of N = 806 adults living in 91 regions of Germany. Results suggest that disengagement predicts increased subjective well-being, but only if individuals report a very high load of demands of career planning and live in regions characterized by particularly poor opportunities for goal striving. It is concluded that disengagement can be an adaptive way of mastering occupational planning under particularly disadvantageous circumstances.