The author of the article draws attention to three developmental trends leading in three directions within the field of career counseling. Firstly, in career planning within the everyday practice of counselors, there is an increasing emphasis on situational factors related to the economic and socio-cultural context. This trend applies equally to issues concerning career development and planning (i.e., preventive programs), as well as to issues concerning the adjustment of already implemented career paths (i.e., intervention programs, primarily for adults). This developmental trend signifies a departure in modern career counseling from theories focused on individual (personality-based) factors toward theories centered on contextual factors—those explaining changes in the nature of work, the labor market, and the broader economic and political environment. Whereas individual-personality theories concentrated on internal factors that explained changes in the self in relation to work and other life roles, contextual theories focus on external situations that, while outside the individual, continuously shape their personality. Secondly, the contemporary emphasis on the contextual factors of career and the strong orientation of modern counseling programs toward differences in the developmental ecologies of various client groups result in success predictors becoming less standardized, more diverse, and increasingly difficult to estimate in terms of effect size (success criteria). Individual variables—such as interests or personality traits (like aptitude or general intelligence)—could previously be measured and their influence on the overall career outcome of an individual estimated. The process of diagnosis, prognosis, and implementing the career path was intensive. Today, intervention and prevention programs in career counseling are becoming more extensive and are less frequently based on intensive diagnosis. The growing necessity to focus on contextual determinants of careers leads to less predictable outcomes, shallower diagnoses, less centralized theoretical foundations, and more reliance on counselors' personal theories. This situation gives rise to numerous paradoxes. On one hand, the more willing and able we are to incorporate a broader empirical data base into the counseling process, include a wider group of so-called non-traditional clients, and utilize a more diversified theoretical base for predicting the outcomes of actions, the less we are able to apply generalizable career counseling theories. The wider the range of clients we are able to serve, the less clearly we can define the success criteria achieved. The less precisely we are able to determine the main effect of career counseling in both preventive and intervention models. Thirdly, regardless of theoretical preferences and the low effectiveness as measured by the main effect size, the foreseeable future of career counseling belongs to models and programs that focus not on individual variables, but on contextual ones. This results from the need to provide career counseling to an increasingly broad and diverse group of individuals from a wide range of developmental backgrounds, as well as from the need to support people in adapting to less standardized life conditions.