Earlier this week, at the urging of a former colleague, I put together my list of the best commencement speeches I’ve heard or viewed online.

The request grew out of a conversation about the late Steve Jobs, the topic of a recent column. Jobs in 2005 was asked to speak to the graduating class at Stanford University, just down the road from his house. And while he had asked for help on is speech, his friends all let him down. He wrote it himself.

Of the form, a commencement speech that is usually filled with conventional advice, his is among the best. Young grads may get something out of it. And for you middle-age folks who understand that you’re lifelong learners, and that your best days may still lie ahead of you, his commencement speech might be a good one to watch.

Another great one came from the writer David Foster Wallace, speaking to the class of Kenyon College, a small liberal arts college in Ohio much like Macalester. His talk called “This is Water” circulated on the Internet for years, and it was published in book form after his death in 2008.

Because his talk is so widely known, I will skip that one and move on to a short list of a few others, great commencement talks for anyone aspiring to challenging work in business.

“Just three stories”

Steve Jobs told the Stanford class that he had “just three stories” to tell from his life. By that time he was well into his second act at Apple, and its resurgence had rehabilitated his own reputation.

The first story he told was about dropping out of Reed College, a prestigious liberal arts school in Oregon. It was costing too much, Jobs said, using up his working-class parents’ savings.

He withdrew from college but did not leave the campus, dropping in to classes and sleeping on the floor in the dorm rooms of friends. The class he told the Stanford grads about was calligraphy, where he came to appreciate the beauty of traditional typefaces like sans serif, and what make great typefaces great.

Years later, when developing the Macintosh computer, it all came back to him. The Macintosh was the first personal computer to have beautiful typefaces, an innovation quickly followed by Microsoft.

Jobs had no way of knowing that calligraphy would ever play any role in his work. He called this an example of connecting the dots.

“So you have to trust that the dots will somehow connect in your future,” he said. “You have to trust in something — your gut, destiny, life, karma, whatever.”

“All of you have been faced with the extra cookie.”

The writer Michael Lewis, a Princeton University grad, told the 2012 class that choosing art history as a major was career “insanity” even back when he graduated in the early 1980s. With not much else to do he went to graduate school, and then by chance he later met the wife of a Salomon Brothers executive at a dinner. That encounter led to a job in the mortgage derivatives group of Salomon Brothers, then a powerful Wall Street trading and investment bank.

It was luck, he said. He had no idea what he was doing at a Wall Street firm. And there he was, put on a perch where he could watch at close range the fundamental shift toward trading and derivatives that would transform Wall Street. It was a topic so rich that the book he later wrote about it, Liar’s Poker, made Lewis rich and famous.

Just like him, he said, the 2012 graduates have been extraordinarily lucky, to have had the parents they had and to have gone to Princeton. The graduates would undoubtedly be presented with much more good fortune in their lives. And after all that good luck it’ll be really easy to conclude that it was all somehow well deserved. That's just not the case, he said, and please to remember that. 

“If you’re offered a seat on a rocket ship, don’t ask what seat.”

Sheryl Sandberg, a graduate of the Harvard Business School and Facebook’s chief operating officer, told the 2012 HBS class a little of her own unconventional career history. Careers are not ladders, she said, they are monkey bars. You’ll go down and sideways as much as up.

In her own case, when eager to leave government she was offered a chance to go to Google, a business she didn’t fully understand. She would be a business unit manager at a company that at the time still had no business units. On her carefully constructed spreadsheet of career options, taking a nonexistent job at Google was no option of all.

The newly appointed Google CEO, Eric Schmidt, told her to not be an idiot and put away her spreadsheet. If offered a seat on a rocket ship, he said, don’t ask which seat, climb aboard.

She climbed aboard.