A Life Lesson from Steve Jobs and You, Me and Dupree for Recent High School Graduates

In You, Me and Dupree, Dupree (Owen Wilson) fills in for Carl (Matt Dillon) and speaks to Molly’s (Kate Hudson) class on Career Day. American values celebrate flying through school, finding a job and joining the professional work force as quickly as possible in order to save dutifully for retirement; the only acceptable alternative is to pursue further education in order to become wealthy doctors and lawyers.

Dupree cannot relate as he has no career. Not only does he lack a career, he lacks a job. And, even worse, he lacks the ambition to find a job. In the words of the great Van Wilder, Dupree is searching for that “dare to be great moment.”

Dupree’s speech challenges the typical career day speaker, who is, shockingly, focused on a career; he is indignant that speakers ignore those like himself who live day to day, following their heart, not a timesheet, worrying more about experiencing life than paying for it.

Career Day trumpets the values of hard work and education in order to become a businessman or doctor. Rarely does a speaker challenge the status quo and articulate an alternative path, the proverbial road less traveled. Instead, when two roads diverge, speakers praise the well-worn path to success, which means following directions, getting A’s, graduating in four years, wearing a nicely pressed suit for interviews, putting your head down and diligently doing your job in order to get a small promotion and miniscule pay raise. It is this kind of inside the box, hopeless pursuit of greatness which troubles Adam Sandler’s character in Click

Dupree does not understand this life; following the beaten path is not in his DNA. Instead, he offers the quintessential carpe diem speech and he champions those who embark down their own path, even if it takes a few more years for these individuals to become responsible adults.