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This is the second of a three-case series. This case tells the story of a functional specialist whose career goal is to become a general manager. Harris Roberts is repeatedly promised a promotion that never comes around. He must decide whether to be patient and improve his internal lobbying efforts, or instead, to look outside the firm, perhaps towards a more entrepreneurial move. This case was designed to open sessions or modules concerned with the career decision making process. What strategies are effective when one decides one wants to make a career transition? How does one garner support, from mentors, sponsors and significant others, for such a transition? What is the process of change? How does one come to define for oneself what one truly wants to do next? The case is designed as a companion to readings from 'Working Identity: Unconventional Strategies for Reinventing your Career' by the same author.