This article presents a reflective account of how gamification can help students overcome complex academic challenges, such as those involved in the dissertation process and other elements of higher learning. Gamification has been shown across multiple levels of academic instruction to have a positive impact on task completion by augmenting the experiential elements encountered by students who are engaging in the learning process. When a task becomes mundane, it typically lacks a positive feedback loop, which results in it becoming easier for a person to put off their intended task and forget to return to the activity prior to deadline. Many online learners participate in their degree programs in the midst of highly involved personal schedules, which can lead to lapses in organization and reduced performance as a student. Many applications have promise for improving the levels of fun, engagement, motivation, and task completion in various areas of daily life. Online faculty, can integrate these applications with existing online curricula to help students bridge the gap between passive stagnation in a course and active engagement with the course material to increase their grades earned and course-wide satisfaction.