Joining the military as a social worker extends far beyond getting hired for a job. The military social worker has entered a path, potentially lasting twenty or more years, which is exciting, treacherous, and often defined by choices made early in the career. Ideally, the naive junior officer is embraced by a mentoring network of seasoned senior social work officers who guide and protect the new person as he or she orients to the new setting. The reality is that the successful new officer is sometimes adrift, does not even know what questions to ask or dangers to protect against, and the network is not aware of his or her existence. This chapter seeks to discuss some of the key issues a new military social worker should consider in building a successful career. For the nonmilitary reader, this chapter can hopefully help you better understand why the military social worker is so focused on issues that seem irrelevant or silly to you.