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.

You, Me and Dupree is a classic; it may not register with the masses, but as one who has spent more than my fair share of time crashing on my friend’ couches, I can more than relate (especially since my nickname one summer was Hansel, after Wilson’s character in Zoolander). My journey has been anything but a straight line, and I have had more than one friend tell me to get a real job, but after you get used to it, being called a gypsy is not the worst thing in the world.

And, the Dupree’s in the world are not just slackers avoiding a job. Many who know me (my sister included) still believe I don’t work. Because I follow my passion, and work my own hours on my own terms, my occupation is valued less than a traditional nine-to-five and friends think I am running a scam or dealing.

Even some productive members of society heeded a Dupree-like path and searched for their “ness,” rather than joining corporate America. So, high school graduate, before heading off to college in the fall, I have three pieces of advice:

First, see Me, You and Dupree. Don’t be Carl.

Second, read Road Trip Nation and Taking Time Off. There are ways to steer off the destined path without assuming a bum-like existence and living on newlywed’s floors. Even the most conservative, follow the path responsible adult will see the value in some of the ideas presented in these books.

Third, if you can’t heed the advice of Dupree, or if you think Dupree is a funny, fictional character with no real life value, check out Steve Jobs’, CEO of Apple Computers and Pixar Animation, 2005 Commencement Address at Stanford University.

Jobs tells three stories. The first is about dropping out of college because it was expensive and he did not see the point; however, dropping out enabled him to take classes which interested him. He took a calligraphy class and later when developing the Mac, recalled the calligraphy lessons and added different fonts. He explains that in retrospect, it’s easy to connect the dots, but you cannot connect the dots moving forward. You must trust something.

One lesson I learned too late in my college education is to pick classes based on interests and professors, not convenience or ease. College is an experience very much up to the individual. It does not matter where you go or what you study; you can have a great experience or a bad experience anywhere. Great professors make for great classes; terrible professors are a waste of time and money. Choose carefully. My best advice is to take some GE classes at a Junior College during the summer, so you can more quickly enroll in upper division, interesting classes. Don’t be married to your education plan; be open to exploration. You never know when a calligraphy class will pay off in the future. I had no idea an Education class with professors’ James Trent, Bruce Barbee and Chip Anderson would be so helpful in my eventual profession as a personal trainer.

Jobs second story is about getting fired from Apple. It happens to the best. But, his firing led to his starting Pixar and meeting his wife. And, he said, “The heaviness of being successful was replaced by the lightness of being a beginner again, less sure about everything. It freed me to enter one of the most creative periods of my life.” One of my favorite lines from a Dilated Peoples song says: “Never forget, you’re still just an artist in debt.” Regardless of your success, never forfeit the creative energy you have when you are just starting out, just creating something and are running on dreams, not money.

Jobs credits his love of his work for getting him through the “awful tasting medicine” and urged the graduates to never give up searching for their passion; don’t settle. It is hard to explain to people who settle and live a nice comfortable life. But, going after your dream, searching for your “ness” and pursuing it with fervor is what one’s professional life is all about.

Jobs final story is about death, and death being a motivating factor for life. Basically, he says life is too short not to live your own life and listen to your own inner voice. He ends with a story about an early 1970’s magazine that ended its run with “Stay Hungry. Stay Foolish.” on the back cover of its final issue. He said he tries to live by those words and urged the graduates to do the same.

Dupree’s life, Career Day speech and search for his “ness” are not unlike Steve Jobs’ speech to Stanford’s Class of 2005. It’s easy to laugh at Dupree and dismiss his message as a comical fantasy; however, it is much harder to ignore the man who invented technology as we know it and use it. Similarly, the otherwise average people who stories are collected in Road Trip Nation and Taking Time Off illustrate ways to follow your passion or take advantage of your youth to discover your passion.

Heed the advice. Stay Hungry. Stay Foolish. Don’t settle. Find your ness.

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