Tough opens up about his own educational journey, revealing that he dropped out of Columbia University in 1985, a decision he contrasts with the determination of students like Kewauna who decided to persevere through college. Tough shares that throughout his time reporting for the book, he grappled with a sense of regret for not having been more purposeful about his college experience.

Tough resonated with the beliefs of Dominic Randolph, the headmaster of Riverdale Country School, who argued that risking failure is an essential experience on the path to success. Randolph suggested that students from affluent backgrounds are often shielded from genuine adversity, which hampers their character development. This rang true for Tough, who at 18 felt compelled to seek out challenges beyond academic success. His quest for self-discovery led him to drop out of college not once, but twice, eventually setting him on a path to become a magazine editor and journalist, and later, to leave a stable job at The New York Times to embark on the uncertain journey of writing How Children Succeed.

Tough also shares that the birth of his son, Ellington, coincided with the writing of this book, prompting Tough to deeply consider what it means to be an effective parent.