Pioneer is a tool for educators, youth practitioners, and researchers to use with young people in order to facilitate thoughts and conversations about youths’ unique goals, interests, and experiences. Young people using the App will be asked to self-reflect and write about the goals they value, an experience that is paired with an embodied set of images linking youths’ goal progress to physical progress along a winding, wooded pathway. Youth then have the option to record and share their self-reflection with peers or educators, either through social media or by simply downloading their responses. In addition, they can revisit their prior entries over time, observing how their responses to Pioneer’s self-reflection questions may change with time or experience. The App experience is brief and flexible, allowing youth to use Pioneer in a variety of settings. For educators and practitioners looking for Apps to help improve youth attention and engagement, Pioneer’s design is based on research on short interventions that improve youth engagement in youth programs, helping young people focus on (and benefit from) learning opportunities that they may otherwise miss. The format of the App allows for individual youth to easily use Pioneer on their own, but youth program leaders can use the program in youth group or even research settings as well. The archiving and sharing functions of Pioneer allow the App to be used in different ways over time, providing a new and flexible tool for youth program leaders.