This chapter aims to empower professionals interested in shifting their learning and teaching practices into progressive approaches that lead to authentic and engaging learning experiences. Far from being a professional biography, this chapter is a reflection on challenges and lessons learned through trial and error. Also included are action research used to implement and internalize cutting-edge research ideas into practice. The author shares experiences that influenced her teaching and learning paradigms in a journey characterized by building learning communities of practice drawing from Project Zero and Habits of Mind ideas to promote lifelong, self-regulated, and authentic learning in children. Her stories of learning address challenges that teachers and administrators go through and avenues leaders can use to empower practitioners to break the mold in education. Learning communities of practice played a critical role in supporting her personal growth as well as teachers’ continuous professional development and practices. Those experiences and stories are a combination of personal and professional experiences in the field in her different roles as a mother, friend, student, teacher, director, researcher, professor, coach, mentor, and leader in different educational initiatives.