Running is a popular recreational sport, yet for many amateur runners it remains challenging to turn intentions into sustainable running behavior. Although the market offers a myriad of running-related devices that aim to motivate runners, these often focus on the training itself and not on overcoming the barriers experienced prior to the run. A better understanding of these barriers to running is essential to identify design opportunities for technologies supporting amateur runners. We conducted two complementary studies among participants of a women-only running event. Combining an online survey (N = 114) and a journey mapping activity (N = 13), we investigated the influence of motivational barriers and enablers in runners' rituals. Based on our findings, we created the Runner's Journey, a visual narrative highlighting actionable design opportunities for running motivation technology. We propose five design recommendations to overcome barriers among amateur runners.