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Education tends to colonize. Established authorities (teachers, curricula, and examinations) instruct newcomers, extending conditional membership. This presents a dilemma for teachers seeking to instill in their students habits of critical, creative, and lateral thinking. In Australia as elsewhere, blueprint educational documents embody lofty aspirational statements of inclusion and investment in people and their potential. Yoked to this is a regime routinely imposing high-stakes basic-skills testing on school students, with increasingly constrictive ways of doing, while privileging competition over collaboration. This chapter explores more informal, organic learning. This self-study narrative inquiry explores my career in terms of a struggle to be my most evolved, enlightened self, as opposed to a small-minded, small-hearted mini-me. To balance this, I examine responsible autonomy (including my own), rather than freedom. This chapter also explores investment in humans, with the reasonable expectation of a return on that investment. It draws and reflects upon events in or impacting my hometown, Sydney, Australia, focusing largely on WorldPride, the Women's World Cup, and a referendum on an Indigenous voice to parliament, all of which took place as I compiled this chapter. Accordingly, the narrative focuses primarily on sexuality, gender, and race. I explore the capacity of my surroundings to teach me and my capacity to learn from my surroundings. The findings and discussion comprise diary-type entries of significant events and their implications for (my) excessive entitlement. The final section of this chapter reviews what and how I have learned.