The purpose of this paper is to describe the nuances of goal setting in coached Masters sport from the perspective of a Masters athlete (MA) who is also a Masters coach. Thus, this paper is an autoethnography of how the first author’s experience in goal setting plays out as a MA with an online coach, and as a coach, coaching other MAs in-person. Data were collected through a series of guided reflexive journal entries, prompted by follow up questions from the second author to create narrative visibility. Journal entries were analyzed to determine what, when, where, how, and why the first author uses goal setting. In Masters sport, goals are set using many of the same principles described in the literature from different sport contexts; however, this autoethnography indicates that it is important for goal setting to originate from the MA to account for individual motives, and then to be communicated with, negotiated by, and supported from the coach with an interdependent, adult-oriented approach.