In this chapter, I provide an in-depth look at how I explicitly planned an individual pursuits unit (cycling, skateboarding, and racquet sports) to not only consider the features of the Meaningful Physical Education (Meaningful PE) approach, but also how I unpacked each of these features with students throughout the unit. I show how the specific feature of challenge was discussed with students in order to help them better understand what were their own entry points to learning in these units. Included in this chapter are practical assessment examples that connect to the features of Meaningful PE and student reflections on their experiences in these units.