Mapping a career and negotiating career transitions can be fraught with challenges and complexities. Those challenges can be arduous, confusing, and complicated, particularly when individuals’ resources, options, dreams, and clarity are limited (Gati, Krausz, & Osipow, 1996; Luzzo, 1995). Scholars have investigated career decision making of individuals across the life span and across cultures (e.g., Bubany, Krieshok, Black, & McKay, 2008; Chung, 1995; Gati, 1986; Gati & Tikotzki, 1989; Luzzo, 1995; Man, 2001, 2004). Gati et al. (1996) proposed three major career decision-making difficulties that occur: (a) lack of readiness, (b) lack of information, and (c) inconsistent information. Individuals at various developmental stages experience feelings of hopelessness and incompetence. Without clear direction, they often simultaneously feel stuck and experience a sense of urgency to find an acceptable and satisfying career path. Regardless of developmental stages, cultural contexts, and unique situations, the process remains complex. Astute career counselors appreciate the complexities and challenges that clients encounter.