Even the most well-prepared athletes are likely to meet challenges, have to adjust game plans, and deal with adversity during competitions, training, and daily life. It has been argued that athletes must have adequate support and be taught skills to ensure that encountering adversity will become a growth experience. Helping athletes prepare for and handle adversity is thus an important task for sport psychology practitioners. In pursuit of confidence, however, when it comes to competitions some athletes (and practitioners) prefer to prepare for and imagine the “perfect race.” The present case study provides an account of how the author has worked to help athletes in the Danish national orienteering team prepare for and handle adversity, with a particular focus on their preparation for a world championship. The applied work took its starting point in acceptance commitment training, was organized as a group setup, and took place in multiple contexts including the gym and the forest. Reflections suggest that daring to prepare for adversity, although unpleasant, is beneficial for athletes and that a group setup potentially promotes normalization and acceptance.