Progress in postoperative pain management depends on the quality of its assessment. Current pain measurements, such as the numerical rating score or visual analog score, oversimplify imprecise characterizations of meaningful recovery and ignore the self-limiting nature of acute pain. This approach does not reveal the pain resolution rate or pain duration. However, defining pain as a trajectory rather than a simple point increases information and improves precision. This course will review the evidence showing the value of using postoperative pain trajectories as a means of predicting postoperative readmissions, emergency department visits, chronic postsurgical pain, and return to work.