I think that this depends on the definition of "messing up" - he missed a financial aid window in 6th grade, and something as trivial as filing a form late had a tangible impact on a year of his life. I think that his point is that this experience conditioned him to view risk quite differently from wealthier peers. I would disagree that "pushing forward" is a valid prescription - the counterfactual "without Mrs. Harris and Head-Royce" leaves him on a different trajectory.