Identifying Information: The Client is a fifty-nine-year-old, white, middle-class transgender woman. She is not married and lives alone in an apartment she owns. Cheri is currently unemployed and has just completed training to become an electrologist. She has past treatment experience having received treatment prior to hormone therapy and sexual reassignment. Current Problem: The client expressed that she is “at a crossroads” and is “having difficulty making financial decisions” about her future. After losing a job of ten years, Cheri recently completed training to be an electrologist and would like to work with other trans women in transition, however she has some difficulty making the financial commitment needed to purchase her own electrolysis equipment. The hesitation led her to doubt her ability to find clients and have a successful business. His current situation has led to feelings of discomfort, distress and uncertainty about his future. These complex emotions left her with a sense of ambivalence about her business plan. She associated this ambivalence with the depression she experienced when she left ballet in her early thirties. She came to therapy to talk about her fears and strong hesitation in making a significant life decision. Cheri expressed that she will find it helpful to have someone to talk to as she explores these fears and contemplates her professional future. History of Presenting Problem: Client has struggled with depression on and off since her twenties. Her depression was alleviated somewhat when she began abstaining from alcohol, but it often returned complicated by feelings of gender incongruence. Cheri attributes therapy and her "helmeted" middle of paper to indecision and hesitation. I was able to maintain adequate rapport with her throughout the interview and she was able to follow directions. He denied any auditory or visual hallucinations. The client has a complete understanding of the nature of her condition. Clinical Evaluation and Formulation: The current challenges Cheri is facing appear to be regulatory in nature. After working in a gallery for ten years, Cheri unexpectedly found herself unemployed. His immediate response was adaptive. He addressed unemployment with an action plan that he proceeded to implement. After completing the courses she is now ready to work as an electrologist. However, he finds himself hesitating due to the cost of the equipment he would need for self-employment. Having benefited from therapy previously, she has now entered therapy to discuss this crossroads in her career.