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Half of my life I have been pursuing a framework for my teaching that could be shared and scaled to be meaningful to underprivileged children who are giving up on their studies instead of seeing education as a way to empowerment out of poverty. I have always been interested in student learning behaviour and how making it visible could support the design of learning plans. I have been fortunate to have lived in a number of different countries and experienced diverse learning approaches, including a free approach as I homeschooled my daughters during a sailing journey around the world. In this chapter, I share some aspects of my quest in academia for a doctorate and how I have used and reflected upon my lived experiences through the process. First, in Brazil as a university lecturer, in New Zealand as a volunteer with education through visual arts, in a boat around the world as a homeschooling mother, in Australia as an educational researcher and tutor, back in Brazil as a project leader of an innovation initiative in a public school, and finally in the United States as a student/researcher at Stanford University’s School of Education. In the longest doctoral rally ever, I reflect on the reasons I am still travelling this journey and the key factors underlying why I have persevered.