This case set describes the decision of a banker (Kaylan Bartholomew) to continue with banking—her dream job—or move to other less remunerative but perhaps more gratifying options such as building a business in wellness and corporate coaching. The A case describes Bartholomew’s professional life in New York and then in her native Trinidad with the Corporate and Investment Banking division at Citigroup Inc. (Citi). The B case provides the aftermath and explains her rationale for what she chose and why. The case set can be used in a course on capital markets as the last case to discuss a banker’s job, its demands, and rewards—and ultimately to help students understand and evaluate the trade-offs between personal and professional life and how to ultimately become a better banker. The cases could also be taught in a leadership module on career path.