This article aims to investigate the structural factors that underpin the current impasse in the development of counseling psychology as a “profession” in Taiwan at both the individual and social level. The author, using her struggles in career and professional practice as a reflective surface, critically examines the problems within the currently established operations in the training, evaluation, and application of counseling psychology since it was institutionalized in Taiwan in 2001. The author takes a step further to discuss the cultural characteristics, assets, and limits that Taiwan possesses in relation to China and other places. Finally, tentative suggestions are proposed, from a socio-economic transition standpoint, on both the positioning of counseling psychology as well as the pathways and stances that counselors and other helping professionals of this generation might adopt in order to advance the profession’s participation and perceived accountability in relation to the general public.