How to Give a Commencement Speech

President Obama gives a lofty address to the Barnard College Class of 2012 today, no doubt full of inspiring ideals and motivational platitudes. Here's why he's doing it wrong.

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Charlie Wheelan

Charles Wheelan, then 22, sits on the side of a dusty New Zealand road, reading "War and Peace," while hitchhiking across the country after graduating from Dartmouth in 1988.

When President Obama takes the podium Monday to give the commencement address at Barnard University, it will be yet another opportunity to show off his oratory skills. We know what to expect: a moving speech that will be filled with ideals of grandeur, motivational platitudes and lofty hopes for the future.

This year’s commencement speakers, as they do every year, will relate inspirational stories of world-altering events and personal stories of overcoming odds (even if the odds were heavily in the speakers’ favor to begin with). What they generally don’t tell you is what Charles Wheelan said to last year’s graduating class at Dartmouth: “Your worst days lie ahead.”

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Wheelan, a Dartmouth grad and college professor, was actually a kind of warm-up act to the Ivy League school’s main speaker: comedian Conan O’Brien. But during his Class Day speech — sort of a pre-commencement address given under less formal circumstances — he won over the crowd with the kind of advice that would likely horrify any college administrator or parent. A failing grade or flawed thesis is nothing, he said, compared to failed job prospects and no money. “To many, it felt liberating,” Wheelan told TIME. “You don’t have a job, and you don’t know what you want to do, but someone is telling you how you’re going to change the world. And you think, ‘That doesn’t describe my life at the moment.’” Wheelan told the Class of 2011 about his friend John, who was on a straight-and-narrow path to becoming an investment banker, but simply couldn’t get a job. He ended up taking the only offer that came his way, in the hotel management field. (Things worked out in the end: John’s now the CEO.)

But the most important lesson? “Don’t make the world worse,” he said. Take, for example, the cigarette company executives, all highly educated men, who testified before Congress in 1994 that their products weren’t addictive. If you’re going to be the graduating class that actually does change the world, try to make sure you change it for the better.

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Wheelan’s advice — including gems like “your time in fraternity basements was well spent” and “Don’t try to be great” — went viral, and for this year’s new crop of grads, he’s compiled it into a book, 10½ Things No Commencement Speaker Has Ever Said. “Most commencement speeches are eminently forgettable,” he tells TIME. “One limitation is that it’s very successful people talking about success, which is what they know, but that doesn’t fully resonate. The parts that resonate most are about failure.”

Sure, Wheelan made it out past his post-graduation awkward phase just fine, but it wasn’t without some classic missteps. Unsure of what he wanted to do with his Asian Studies degree, he decided to travel the world for nine months, but returned with “no job and no money” and ended up living on the couch of a 70-year-old married couple. In the 24 years since then, he’s been a speechwriter, a journalist, a public policy expert and a college professor — an ultimately successful growth process that was nevertheless tinged with disappointment. So he felt it important to draw on his own failures in telling graduates they would come out better and stronger having struggled than if everything were dished out on the proverbial silver platter.

(WATCH: Stephen Colbert Delivers Genuine (and Hilarious) Northwestern Commencement Speech)

Every speaker gives examples of minor missteps, mostly to prove they’re human. J.K. Rowling, author of the best-selling book series in history, noted to Harvard’s outgoing class in 2008 her classic rags-to-riches story: “An exceptionally short-lived marriage had imploded, and I was jobless, a lone parent, and as poor as it is possible to be in modern Britain, without being homeless.” Even Steve Jobs’ famous Stanford address in 2005 drove home some immense failures in his life: “What had been the focus of my entire adult life was gone, and it was devastating. I really didn’t know what to do for a few months. I felt that I had let the previous generation of entrepreneurs down – that I had dropped the baton as it was being passed to me.”

But in today’s disappointment-prone world, where students will emerge with insurmountable debt and rampant uncertainty about their life’s paths, commencement speakers like Wheelan do well to focus on the disappointments in life, with the underlying message that there are better days ahead. It’s OK, they can handle it – they’ve dealt with four years of professors piling us with endless work in classes for which they burned the textbook the day after the final. Graduates want to hear it like it is. So why shouldn’t speakers tell it?

PHOTOS: Let the Graduations Commence: The Class of 2011