The chaos theory of careers emphasizes both stability and change in its account of career development. This article outlines counseling strategies derived from this emphasis in terms of convergent or probability thinking and emergent or possibility thinking. These 2 perspectives are characterized, and practical counseling strategy implications are provided. In addition, an illustrative technique example is described. The authors conclude that the challenges of modern career development demand the complementary and the interactive use of both probability and possibility thinking strategies. (Contains 1 figure.)