The grief process is a lifelong journey. Something we will all experience as we walk alongside the amazing people in our lives. Reflecting on the grief journey Riley experienced when losing his son Colin suddenly in 2018, he found that he grounded his grief in the design methodologies he had spent his life developing. This presentation grounds our work as designers and technology experts in empathy, and authenticity. How do we bring that empathy to the teams we work with every day? How do we bring empathy to our work, even when we are expected to deliver in an environment that expects fast paced development? Riley’s stories will connect his work in government to the grief that is part of his everyday life.