When faced with unknowns, there are those who wait and those who figure-it-out. For middle school students to be happy, healthy, and successful, they need to be able to independently navigate the unknown—to figure-it-out, no matter what it is. Figuring-it-out refers to a person’s ability to independently solve problems or determine a workable solution through their capacity to regulate, cope, apply strategies, and take action. This capstone project uses a five-part professional development series for educators to answer the question, how might the explicit teaching of figuring-it-out combined with sustained practice help students to become more independent? The series emboldens teachers with the background knowledge and savvy they need to explicitly teach and sustain the practice of the transferable problem solving competence skills of figuring-it-out. In the series, these skills are explored and practiced using an andragogical and transformational approach. Time for self-reflection, collaborative work, and future planning is embedded