The author presents 11 essays on teaching education, with a focus on the intersection between troubles and issues and life experience and history. The essays in the first section address neoliberalism and teaching education, particularly the institutional, ideational, and social context of educators, including neoliberalism and its effects on education and educators; the evolution of the purposes and practices of teacher education under neoliberal policy priorities; the ideology, biases, and intentions in the National Academy of Sciences publication Preparing Teachers; and problems with the idea of "best practice." Essays in a second section explore aspects of the inner experience of teaching, with an emphasis on troubles and issues, including educational reform and the role of motivation, teacher identity within a neoliberal audit culture, the role of storytelling and parables in teaching, the role of vulnerability in learning and teacher development, problems with the emphasis on empathy in teaching, the dangers and benefits of humor in teaching, and the well-being of teachers.