Educational leadership preparation should include the integration and influence of philosophy, liberal education, and the humanities to further students’ ability to think and lead well and to help them understand and appreciate liberal education’s value, so its benefits flow to teachers and their students. This essay is primarily reflective, personal, and philosophical in nature. This essay is assuming the general value and importance of the historic Western liberal learning and liberal arts tradition: that this tradition and its essential values are still good for and necessary in 21st-century education. Applied in the context of this essay, this means not only guiding our educational leaders to think well, but also steering their hearts toward right action based on humane principles such as compassion, justice, and equality, all based on respect for the dignity of every person.