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The author shares his experience of teaching history to college students by referring to the class Dirty Wars and Democracy which examined the Southern Cone of South America from the 1960s to the 1990s. Topics discussed include dictatorships, his approach to teaching at Oberlin College, the importance of students' location in an environment, and the critical thinking ability of educators.

The author discusses his experience of counseling a student and going to orientation night for parents of kids heading into kindergarten and mentions a student's time at a liberal arts college. Topics discussed include the idea of teachable moments, liberal arts education, virtues like self-confidence or self-esteem, and young adults drawn to small, selective liberal arts colleges.

The author talks about liberal arts education by referring to the rise of universities such as Oxford during the Middle Ages and mentions the importance of liberal arts colleges for students. Topics discussed include knowledge, wisdom, and virtue, the paradoxical virtue of the liberal arts, encouraging students to think within the norms and conventions of a variety of disciplines, and critical thinking.

The author shares his experience of applying to a liberal arts college in the U.S. as a Sri Lankan student and mentions his ignorance about the difference between American universities and Sri Lankan universities. Topics discussed include pure mathematics, applied mathematics, physics, and chemistry as his subjects, his computer skills, his college education at the Oberlin College, and taking an economics course.