Acknowledging the scarcity of a bottom up social work practice model in facilitating the development of success in workforce development programs, this study explores Psychological self-sufficiency (PSS) as an emerging social work practice theory. Phenomenological studies of low-income jobseekers in employment training along with the empirical validation of measures of the core constructs of PSS – employment hope scale (EHS) and perceived employment barrier scale (PEBS) – and testing of the theoretical model resulted in the emergence of a new theory of PSS. PSS was conceptually defined as a dynamic and internal drive that activates the process of transforming cognitively and affectively perceived barriers into hope driven action – the process that enables individuals to move forward toward goals. Based on the evidence of PSS, a participant-centered group intervention model called transforming impossible into possible (TIP) program was developed. This article delineates the trajectory of PSS theory development by critically reviewing various streams of practice theories influencing the PSS theory. Next, the conditions that necessitated the creation of the TIP program and its core principles underlying the functions of PSS are explained. By depicting the TIP program with direct quotes of clients’ experiences, authors exemplify the successful self-discovery process through enhanced PSS skills as a result of participating in the TIP program.