This study compares two different methods of headstand practice. One is a practice progression inspired by breaking (dance) that can be practiced on hard ground and the other is a common trial-and-error method as practiced on gymnastics mats. This study includes analyses of data gathered from field observation, one randomized control trial, and one intervention treatment. All three analyses reveal that the breaking headstand practice progression on hard ground results in significantly less occurrences of crashing when compared to the trial-and-error-based headstand practice on gymnastic mats (p < 0.5). This could mean that this method is the safer of the two, and also support the claim that use of good method is more important than the presence of safety equipment when assessing the risk of a physical activity. Further investigation should be done on breaking training methods, as well as other material-independent athletic skill training methods, so to increase and perfect physical education and dance-related pedagogical content knowledge.