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By their very nature, policing and mediation are viewed as disparate professions. However, since the inception of policing, police officers have traditionally been involved in managing and handling conflict situations and thus, mediation type interventions have historically been an important component of police work. For the most part, police officers are untrained in mediation; however, many police officers are comfortable serving as go-between for neighbors, families, and communities in conflict using their intuition. As a result of acting as a ‘mediator’ for conflicting parties, without any formal mediation training, many former and current police officers eventually engage in mediation training and become certified mediators, as I did. Despite this occurrence, there is sparse scholarship on police officers who become mediators. As a result of this lacuna, the current study describes my journey from being a police officer to becoming a certified mediator. In this article, I describe how I utilized my intuition and police training to resolve conflicts without being a certified mediator; successes and failures encountered; community and organizational impacts; and how the conduct of informal mediation facilitated my eventual transition to a certified mediator with the Mediation Board of Trinidad and Tobago. Using evocative autoethnography as the fulcrum of inquiry to analyze aspects of myself, I trace my circuitous journey to becoming a mediator.