Natalie Melchiorre wanted to work on her upper body strength so she decided to start a 100-pushup challenge. Using a popular iOS app she followed a plan and tracked her progress as she increased her strength. Along the way she encountered some hurdles, but continued on. In this talk, presented at the Phoenix Quantified Self meetup group, Natalie describes her experience with setting this ambitious goal and what she ultimately learned when she failed to complete it. Make sure to stick around to hear Natalie talk about the intersection of goals, performance, and identity.