The librarian retirements and librarian shortages predicted over the last 20 years have not come to pass. A myriad of factors are at play, including healthier and longer life spans and the desire to stay actively involved. But the decimation of many retirement funds during the 2008 recession, fluctuating finances, and personal needs have contributed to many academic librarians remaining in the workplace far beyond when they had hoped to retire. Some are working not because they want to, but because they must. With their years of experience, these librarians are viewed as either irreplaceable resources to their libraries and institutions or irritating impediments to progress. While career trajectory conversations commonly occur with early and middle career librarians, we have been remiss in having these kinds of conversations with our later career colleagues. It is the elephant in the room that has been ignored. Talking about the elephant may support effective job performance as well as succession planning. Identifying and utilizing existing resources within our organizations to support and motivate later career librarians, develop strategies to help inspire these librarians to making their end game their best game, and creating environments in which all make meaningful contributions and thrive are discussed.