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The authors identified 146 city managers who have served in the same city for the past 20 years and asked them to complete a survey to determine the factors leading to their long service. As a part of the survey, the city managers were invited to express, in their own words, the reasons they had stayed in the same city for such an extended time compared to the average tenure for city managers. In the article that follows, the authors quote from the academic literature statements pertaining to practical issues of concern to city managers and the elected officials for whom they work, giving credence to the applicability of the academic literature to today’s city management profession. Following the quotations from the literature, the authors present the heartfelt reflections of these senior city managers on their long careers in public service.