To begin, take a moment to reflect on the three terms that constitute the title of this chapter: psychotherapy, counseling, and career counseling. Now, take that moment. What do you think? How might you describe their differences and similarities? What key terms or constructs might you deploy to differentiate or integrate them? By posing these questions, is it a simply a matter of rhetorically positing differences that do not exist? What practical differences are there? Are they merely different labels for the same thing? What societal value might you ascribe to each? Does it really matter that much anyway? These questions underpin the reflective purpose of this chapter. This is an opportunity for you the reader to (re)consider vocational psychology, including psychotherapy, counseling, and career counseling. This chapter presents a philosophical analysis of psychotherapy, counseling, and career counseling, and takes into account history and epistemology. Methodologically, this chapter is an inspection of vocational psychology's discourse (cf. Richardson, 2012b; Stead & Bakker, 2012); for it is the discourse of vocational psychology that establishes and delimits the questions that generate research endeavors, the knowledge that identifies and differentiates the field from other branches of applied psychology, how its knowledge is transmitted, and the activities that constitute its professional practices, such as career counselling and career education. Rather than merely rehearsing explicit knowledge of theories of psychotherapy, counseling, and career counseling that can be read in a book or journal article, the chapter reveals issues pertaining to tacit knowledge and their paradigmatic roots.