This paper explores how prospective professionals, including those outside of educational institutions, approach entering the cybersecurity field. Through qualitative interviews with individuals planning a cybersecurity career, we explore diverse challenges they face during their journey to enter the profession. Our preliminary analysis suggests their challenges may include a lack of awareness of occupational culture, insufficient domain-specific language, visibility into the practitioner community, and differences in expectations between new and practicing professionals. By complementing prior research focused on university education and training programs, this work aims to uncover the challenges of individuals on a broader spectrum, such as those attempting to change careers and “break in” to the profession.