The purpose of this phenomenological study was to understand how two midlife adult men experienced different levels of expertise as they transitioned between non-teaching and teaching professions. Of further interest were the unique qualities that these mid career changers brought to secondary education and their recommendations for improving preparation, induction, and retention of midlife career changers in teaching; The study examined the transition experiences through three dimensions: (1) the levels of creativity in the context of environments; (2) the physical, social, and emotional development of the individuals; and (3) the theoretical framework of expertise. Semistructured interviews were conducted, and analyses were made by horizontalization, categorization, and textual and structural description. Interpretation of the data was made through the phenomenological themes of spatiality, temporality, and relationality; The two participants in this study performed at advanced levels of problem solving and creativity and brought rich lived experiences to their new professional environments. Their abilities to filter problems through their own lived experiences allowed them to create learning environments that motivated students to succeed; The results of the study indicated that both participants were discouraged because their school environments did not: (1) encourage the type of creative problem solving and teamwork that they had experienced in their former professions, (2) account for ineffective teaching behaviors, and (3) promote sufficient professionalism; The emotional lows that accompanied the lack of requisite knowledge to perform specific tasks or to be received as a professional instead of a novice were critical to the experience of transitioning between expert and novice levels of performance. Both participants quickly adapted to their new professions by viewing the entire school community as their professional domain; Implications from this study include a need to: (1) create preparation and induction programs that are tailored to meet and compliment the unique strengths of midlife adults who change professions, (2) provide opportunities for mid-career changers to continue using their creative problem solving talents, and (3) give voice to mid-career changers and mid-career teachers to create synergism and symbiosis