The decision to undergo sex reassignment surgery is known to produce long-term social and psychological effects. Many of these effects can be observed long after the procedure. The following paper outlines two main challenges an individual might face and explains strategies that can be used to address them. The first challenge likely to be faced by a client occurs at the lead-up phase of sex reassignment. This challenge is caused by social, psychological, and emotional disturbances related to changes in the client’s status in society. The most apparent aspect of the challenge is the acknowledgment of their identity to the peers and, to an even greater extent, relatives. The review of personal testimonies reveals that in many cases, impacted individuals feel the difficulty of accepting the idea of achieving their goals and living normal lives after coming out (Laureate Education, 2014). Disproval of parents or other relatives may aggravate the situation (Levine, Risen, & Althof, 2015). It has been suggested that disclosure of such information can produce an experience of personal growth that serves as a major factor in the process of identity development (Vaughan & Waehler, 2009). While the process may yield positive personal and social identity, it is important to acknowledge that it involves significant exposure to stressful experiences. The second challenge is expected to be faced by a client during a post-reassignment period. The nature of the challenge in question is twofold. On the one hand, after the surgery, an individual undergoes a significant reorientation that involves adaptation to a new role on a personal level and, more importantly, coping with stigmatization, discrimination, and bullying (Levine et al., 2015). The latter is associated with a suicide rate nine times higher than that of the general population (Rocero, 2014). On the other hand, surgery is known to have unpredictable effects on sexual orientation. According to the available data, female-to-male transgender persons can display one of four patterns of sexual behavior (Rowniak & Chesla, 2012). Understandably, in many cases, these changes can create additional emotional and psychological pressure. The identified challenges can be addressed through a number of strategies. Specifically, the lead-up phase concerns can be mitigated by affirming the possibility of the client to live a functional and emotionally satisfying life while at the same time acknowledging the potential of stigma and gender-conforming pressure. In addition, it would be beneficial to discuss the decision-making approaches to employment, healthcare, and housing in the context of oncoming surgery. In many cases, the strategy needs to be adjusted to account for intersecting identities of the client, such as ethnicity, class, spiritual affiliation, and any specific experiences identified by the client and relevant to the situation. Finally, it is important to establish an open and honest communication channel with the client’s family by communicating to them the significance of their support while at the same time address possible misconceptions and/or prejudices present among the relatives (Burnes et al., 2010). In this way,