Back in 2005, Jobs spent months trying to figure out what to say to Stanford’s graduates. Newly released materials show how he went from hopelessly flailing to delivering a talk for the ages.

In early June 2005, Steve Jobs emailed his friend Michael Hawley a draft of a speech he had agreed to deliver to Stanford University’s graduating class in a few days.

“It’s embarrassing,” he wrote. “I’m just not good at this sort of speech. I never do it. I’ll send you something, but please don’t puke.”

The notes that he sent contained the bones of what would become one of the most famous commencement addresses of all time. It has been viewed over 120 million times and is quoted to this day.

Probably every person who agrees to give a commencement speech winds up re-watching it, getting inspired, and then sinking into despondency. To mark the 20th anniversary of the event, the Steve Jobs Archive, an organisation founded by his widow, Laurene Powell Jobs, is unveiling an online exhibit with a remastered video, interviews with some peripheral witnesses, and ephemera such as his enrolment letter from Reed College and a bingo card for graduates with words from his speech.

“Failure,” “biopsy” and “death” were not on the card, but they were clearly on Jobs’ mind as he composed his remarks.

Jobs dreaded giving this speech. The Jobs I knew stayed in a strictly policed comfort zone. He thought nothing of walking out of a meeting, even an important one, if something displeased him. His exacting instructions to anyone charged with preparing his meals rivalled those for the manufacture of iPhones. And there were certain subjects that, in 2005, you best never broach: the trauma of his adoption, his firing from Apple in 1985, and the details of his cancer, which he held so closely that some wondered if it was an SEC violation.

So it’s all the more astonishing that he set out to tell precisely these stories in front of 23,000 people on a scorching hot Sunday in Stanford’s football stadium.

“This was really speaking about things very close to his heart,” says Leslie Berlin, executive director of the archive. “For him to take the speech in that direction, particularly since he was so private, was incredibly meaningful.”

Jobs actually wasn’t the graduating class’s top choice. The four senior co-presidents polled the class and number one on the list was comedian Jon Stewart. The class presidents submitted their choices to a larger committee, including alumni and school administrators. One of the co-presidents, Spencer Porter, lobbied hard for Jobs.

“Apple Computer was big and my dad worked for Pixar at the time, so it was the obvious thing that I represent the case for him,” Porter says. Indeed, legend has it that Porter was the inspiration for Luxo Jr, the subject of Pixar’s first short film and later its mascot. When his dad, Tom Porter, brought Spencer to work one day, the story goes, Pixar auteur John Lasseter became entranced by the toddler’s dimensions relative to his father’s and got the idea for a baby lamp. In any case, Stanford’s president, John Hennessy, liked the Jobs option best and made the request.

By this point Jobs had declined many such invitations. But he’d turned 50 and was feeling optimistic about recovering from cancer. Stanford was close to his house, so no travel was required. Also, as he told his biographer Walter Isaacson, he figured he’d get an honorary degree out of the experience. He accepted.

Almost immediately Jobs began to second-guess himself. In his own keynotes and product launches, Jobs was confident. He pushed his team with criticism that could be instant and corrosive, even cruel. But this was decidedly not an Apple production, and Jobs was at sea as to how to pull off the feat. Oh, and Stanford doesn’t give out honorary degrees. Whoops.

On January 15, 2005, Jobs wrote an email to himself (Subject: Commencement) with initial thoughts. “This is the closest thing I’ve ever come to graduating from college,” Reed College’s most famous dropout wrote. “I should be learning from you.” Jobs – famous, of course, for his ultra-artisanal organic diet – considered dispensing nutritional advice, with the not terribly original slogan “You are what you eat.” He also mused about donating a scholarship to cover the tuition of an “offbeat student.”

Flailing a bit, he reached out for help from Aaron Sorkin, a master of dialogue and an Apple fan, and Sorkin agreed. “That was in February, and I heard nothing,” Jobs told Isaacson. “I finally get him on the phone and he keeps saying ‘Yeah,’ but … he never sent me anything.”

One day at Pixar, Jobs ran into Tom Porter. As Spencer Porter says it, Jobs asked Tom if his son could send over a few pointers. The students sent Jobs some thoughts. Hennessy told him to forget abstract advice and make the speech personal.

Eventually, Jobs recruited his old friend Michael Hawley to help him out. Hawley was a polymath associated with the MIT Media Lab. A brilliant technologist, he was once a co-winner of a worldwide piano competition for “outstanding amateurs” and he later organised a TED-like conference called EG. Hawley had worked with Jobs at Next and even shared a house with him at the time. They had kept in close touch.

Hawley’s contribution to the speech has been somewhat of an open secret for years. Still, there is no mention of him in Becoming Steve Jobs by Brent Schlender and Rick Tetzeli, which devoted a chapter to the speech. The Isaacson biography doesn’t cite him and neither does, surprisingly, the exhibit at the Steve Jobs Archive. In an online Festschrift for Hawley in April 2020, Jobs’ son Reed spoke about Hawley’s role, including the “don’t puke” email quoted above. But Hawley never spoke publicly about exactly how he helped Jobs – except for one day in 2020, while driving around Boston with the journalist John Markoff a few months before Hawley’s death at age 58 from cancer. Markoff recorded the conversation, none of which has been made public until now.

As Hawley recounted to Markoff, Jobs first tried to get him to deliver the address. “He told me he was hoodwinked, as he put it, into giving a speech at Stanford and just didn’t know what to say or do,” Hawley said. “He wanted to turn it down, he wanted to get me to do it instead. I said, ‘No way – it’s your gift.’ He then basically begged me, in a very sweet way, a very Steve way, to help him out. And I said sure.”

Hawley loved Jobs’ idea of opening with his own experience of not graduating from college. Jobs had been kicking around the idea of giving the students “three pieces of advice as you leave college.” The first would be about “surrounding yourself with people smarter than you.” He didn’t seem to have a second. The third was built around the fact that “we are all going to die. You are going to die.” A few days later, Jobs drafted some lines about the Whole Earth Catalogue, figuring some notes on its final issue might work as a potential ending to his speech.

“He had the closing idea before he had any of the content of the speech,” Hawley said. He urged Jobs to strengthen the kicker. “Like a good comedian telling a joke or a good composer writing a piece of music, you want to be sure to nail the punchline, so I think maybe think more about the ending,” he wrote to Jobs in an email.

“I like your Whole Earth recollection a lot. I grew up with it too. Even the phrase WHOLE EARTH taps a powerful idealistic undercurrent.” He suggested a few tweaks and reminded Jobs that he’d have to explain what the catalogue was. As Hawley told Markoff, “I said, ‘Look, this was Google for our generation … And I said for god’s sake, give credit to Stewart Brand, whose poetic touch infused all that and so much more.”

The archive exhibit contains eight emails that Jobs sent himself. There’s a gap between early May and June; presumably, Jobs was preparing for a more familiar sort of presentation at that time: his opening keynote at the Apple Worldwide Developers Conference on June 6.

Onstage in San Francisco that day, Jobs was masterful, stalking the stage in alpha fashion, explaining a new phenomenon called podcasting (“We see it as the hottest thing going in radio”) and the Macintosh’s switch from PowerPC to Intel processors. But the Stanford deadline was looming. By June 7, he was back to sending emails to himself. Hawley told him that, just like an undergraduate, he might have to pull an all-nighter to finish the speech.

• A Tell Media report / Originally published by Wired