In an era of social justice warfare, the term “empathy” has become a hollow siren signal and the overuse has given it an inaccurate connotation that does not match its definition. This misunderstood definition paired with the myriad interests competing for coaches’ attention can make developing empathy and emotional self-awareness feel unimportant. My goal over the next few months is to break down the three different types of empathy, (emotional, cognitive, and compassionate) and then make a case for why they are so important for coaches to understand and develop while also giving strategies based on my experience and the literature for how to better connect with athletes. I will chronicle the journey I have been on the last few years in hopes that my experiences, failures, and subsequent lessons I have learned will help other coaches. I will share in detail my transition from being an overbearing, authoritarian taskmaster who pretended to be enlightened to being a practitioner who prioritizes empathetic engagement over programming, training, and all other physiological variables. I do not consider my experiences to be unique and I am far from an expert, but I think the way I processed and learned from my experiences is unique. I look forward to hearing your thoughts and feedback in the future!