Purpose: This study explored the career development experiences and well-being of counseling psychologists who engage in self-media entrepreneurship as a form of slash career. Specifically, using the PERMA (Positive Emotion, Engagement, Relationships, Meaning, and Accomplishment) framework as an interpretive lens, it sought to understand (a) their motivations for entering self-media work, (b) the challenges encountered during this career trajectory, and (c) how well-being is experienced and constructed throughout this process. Methods: A narrative research approach was adopted to capture the lived career experiences of counseling psychologists operating across professional and public domains. Data were collected through semi-structured, in-depth interviews and analyzed using both holistic and categorical content narrative analyses. This dual analytic strategy allowed for the reconstruction of individual career trajectories while also identifying shared thematic patterns across participants. Participants consisted of five licensed counseling psychologists in Taiwan who met the following criteria: (a) at least one year of professional counseling practice, (b) at least one year of continuous self-media operation, and (c) a primary social media platform with more than 10,000 followers. Participants varied in age, years of practice, media platforms, and content formats, providing a diverse yet information-rich sample suitable for narrative inquiry. Results: Participants’ entry into self-media entrepreneurship was primarily driven by a desire to extend the reach and impact of counseling beyond the traditional consultation room. Self-media platforms enabled participants to translate professional knowledge into accessible content, thereby transforming conventional one-on-one helping relationships into scalable, one-to-many modes of psychological outreach. For many, this expansion functioned as a compensatory response to institutional constraints, such as administrative burden, limited professional autonomy, or restricted opportunities for broader social influence within formal organizational settings. Three major career challenges were identified. First, participants described the psychological impact of platform-based performance indicators, including likes, views, and follower counts. These visible metrics often shaped emotional responses and professional self-evaluation, requiring ongoing self-awareness and emotional regulation to prevent external validation from overshadowing professional values. Second, participants experienced persistent tension between the depth required in counseling practice and the fast-paced and simplified nature of social media communication. Translating nuanced clinical knowledge into brief, engaging content posed both technical and ethical challenges, prompting participants to adopt adaptive strategies, such as maintaining parallel professional roles, narrowing content focus, or intentionally slowing production. Third, participants faced ethical dilemmas related to commercialization and boundary management, particularly regarding sponsorships, public self-disclosure, and requests to share clinical material. Across cases, participants emphasized prioritizing professional ethics and client welfare, even when such decisions limited commercial opportunities. In terms of well-being, participants’ experiences reflected a distinctive configuration of PERMA elements. Meaning and accomplishment emerged as the most salient and tightly interconnected dimensions. The ability to influence unseen audiences, receive longitudinal feedback, and witness personal or professional impact over time fostered a strong sense of purpose and achievement. Positive relationships extended beyond traditional professional boundaries to include audiences, peer creators, and supportive personal networks, forming a multilayered system of social connections. Positive emotions such as excitement, pride, and fulfillment were frequently reported but appeared episodic rather than central. Engagement, or deep absorption in work, was not described as a primary pursuit but rather as a natural byproduct of meaningful and value-consistent activities. Discussion: The findings suggest that counseling psychologists’ well-being in slash careers is best understood as a dynamic and process-oriented experience rather than a static accumulation of discrete PERMA components. Meaning and accomplishment appear to function as core drivers that give rise to engagement and positive emotions over time, while relationships serve as a stabilizing context that sustains long-term involvement. Based on these patterns, this study proposes a culturally grounded perspective of “dynamic PERMA unfolding,” highlighting how well-being evolves through ongoing negotiation between professional values, public engagement, and ethical reflexivity. Practically, the results underscore the need for counselor education and professional training to address emerging hybrid career forms that integrate counseling expertise with digital media and public scholarship.