Crazy awesome

Conan O'Brien, Shonda Rhimes, Steve Jobs, and 7 other things worth your time

We're in the middle of graduation season (virtual, anyway) and before it all ends I wanted to share something I've learned from commencement speeches.

I studied these a bit when I was doing a lot of ghostwriting. I know how to write books, but I had to learn how to write speeches—and these addresses are a great way to learn about pacing, structure, language, and even content.

The ones that work very well seem to have a few things in common. For one thing, almost no matter how renowned the speaker is, he or she understands that the audience has traveled from near and far to see the graduates, not them.

At best, they’re a great opening act. So the smart ones keep an eye on the clock.

And, unless they’re using the speech as an opportunity to make some kind of political statement (like say, Winston Churchill’s Iron Curtain speech at a Missouri college in 1946), their theme is always authenticity.

Not “fake authenticity,” but real, deep, truthful connection.

(In fact, I know this runs a bit long today, so TL;DR: “Authenticity always wins.”)

Here are three speakers that I think did it very well, and that I’ve gone back to a few times as a result.

Conan O’Brien at Harvard in 2000

“The last time I was invited to Harvard, it cost me $110,000,” Conan O’Brien said as he opened this address in 2000.

At the time, he was in his seventh season hosting Late Night on NBC, with 2.5 million visitors each night. But while literally every paragraph of this speech ends with a joke, O’Brien talked almost exclusively about monuments to his failures.

Things like driving a 1977 Isuzu Opal, working at Wilson’s House of Suede and Leather when he got to California, getting jobs on shows only to have them get canceled, and then having the chance to create a TV pilot—only to see that get abandoned, too.

Even his big break, being hired out of nowhere to host Late Night in 1993, is tempered in the speech by Conan quoting a hilariously bad review that called him a “fidgety marionette,” and “a living collage of annoying nervous habits.”

“There’s more, but it gets kind of mean,” Conan said. And while self-deprecating humor is kind of his schtick, the honesty makes it work.

“To be honest with you, it hurt like you would not believe. But I’m telling you all this for a reason. I’ve had a lot of success. I’ve had a lot of failure. ...

But my mistakes have been necessary. I’ve dwelled on my failures today because, as graduates of Harvard, your biggest liability is your need to succeed, your need to always find yourself on the sweet side of the bell curve.”

Shonda Rhimes

Shonda Rhimes graduated from Dartmouth in 1991, and came back to give the commencement address in 2014. Her speech is also authentic, but it works differently.

As an example, she admits how excited she is to be there—but doesn’t fall into a trap of pretending she doesn’t think she’s worthy of the honor. It’s a tough line to walk.

“I checked and it is pretty rare for an alum to speak here,” she said at one point. “It's pretty much just me and Robert Frost and Mr. Rogers, which is crazy awesome.”

Let’s just address two other points. First, she says she never reached her college-dream, which was to be more of a Toni Morrison, Nobel Prize-winning type author, rather than the creator of very popular television shows.

But this turns into an admonition to the graduates to be doers, not dreamers. (“I worked really hard. And I ended up building an empire out of my imagination,” she said. “So my dreams can suck it.”)

Second, she comes clean in that she—and everyone else—falls short constantly.

“Whenever you see me somewhere succeeding in one area of my life, that almost certainly means I am failing in another area of my life.

If I am killing it on a Scandal script for work, I am probably missing bath and story time at home. If I am at home sewing my kids' Halloween costumes, I'm probably blowing off a rewrite I was supposed to turn in. …

That is the tradeoff. That is the Faustian bargain …

See what I mean? She’s not self-deprecating like O’Brien, but she admits the things that might be less than flattering, and never shies away from her achievements. It adds up powerfully.

Steve Jobs

I always come back to this speech: Steve Jobs at Stanford in 2005.

As we’ll see, the authenticity here is powerful—largely because of the content. First, he starts out by acknowledging that the speech itself is the closest he ever came in life to a college graduation. (He dropped out of Reed College.)

The next line is gold: “Today I want to tell you three stories from my life. That’s it. No big deal. Just three stories.”

I don’t think I’ve ever seen better structure in a speech, anywhere. Jobs tells the audience exactly what they’re going to get, deflates expectations, and delivers. It breaks down like this:

  • “The first story is about connecting the dots.” This story lays out his life—from birth, through adoption (and nearly being adopted by another family), through when he dropped out of college. The crescendo is about how he once studied calligraphy, which led him to insist later on the revolutionary idea that computers should display multiple typefaces and proportionally spaced fonts.

  • “My second story is about love and loss.” This turns out to be about building Apple, being fired from it, and ultimately realizing that it was “was the best thing that could have ever happened to me,” because it forced him to start over and build something else.

  • “My third story is about death.” This last one is so poignant now, as Jobs talked about his bout with pancreatic cancer and recovery, and how it focused his attention on life and death. At one point he calls it, “the closest I’ve been to facing death, and I hope it’s the closest I get for a few more decades.”

Of course, Jobs didn’t get a few more decades; he was gone a little more than six years later—much less time than he thought he had when he was speaking. That’s what makes this last part so gripping, at least to me:

No one wants to die. Even people who want to go to heaven don’t want to die to get there. And yet death is the destination we all share. No one has ever escaped it.

And that is as it should be, because Death is very likely the single best invention of Life. It is Life’s change agent. It clears out the old to make way for the new.

Right now the new is you, but someday not too long from now, you will gradually become the old and be cleared away. Sorry to be so dramatic, but it is quite true.

Your time is limited, so don’t waste it living someone else’s life.


We have others, many others. Admiral McRaven at Texas, J.K. Rowling at Harvard (again with Harvard). Plus, Robert Smith at Morehouse College last year has to go down as one of the most memorable speeches ever.

It’s probably out of reach for most speakers to agree to pay off the educational debt of the entire graduating class, like Smith did. The less expensive secret: Authenticity (and keep your eye on the clock).

If you don’t learn anything else in college, these are some pretty good lessons to pick up on your way out the door.

7 other things worth your time

  • Walmart announced it’s going to shut down Jet.com, which it bought for $3 billion in 2016. (TechCrunch)

  • Forget the handshake. In France, they’re adjusting to the idea of saying goodbye to “la bise," the double kiss-on-the-cheek greeting that’s been de rigeur for decades. (WSJ, $)

  • Wow, I just keep thinking through how this could ultimately have big ripple effects in society if it catches on: In Tampa, the city is closing some streets so that restaurants can take over the real estate to increase outdoor seating and social distancing. (CNN)

  • The U.S. will reportedly demobilize 40,000 National Guard members working on Covid-19-related projects on June 24. The date is important because it means they’re one day short of the 90 days of active duty they need to qualify for education and retirement benefits. (Politico)

  • The FBI says it cracked a Saudi terrorist’s iPhone with “effectively no help” from Apple. Apple denies it hasn’t helped, but it’s the latest round of a dispute over whether the company should provide a “backdoor for law enforcement” in its secure products. (Fortune)

  • A 90-year-old woman in Japan made the Guinness Book of World Records for being the oldest YouTube gamer. (Guinness)

  • The CBS Evening News program was knocked off the air Tuesday by a technical issue. Apparently it was harder to fix because almost nobody is actually working at the CBS Broadcast Center in New York due to the pandemic. (Variety)

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