Conan O’Brien and The Art of Low Expectations

Turns out happiness IS what you make of it.

Have you seen Conan O’Brien on the YouTube show Hot Ones?

Since it was posted four days ago, it’s been seen millions of times, and GIFs are everywhere.

It’s a ridiculous watch, escalating into madness over the course of 27 minutes.

It’s such a work of visceral comedic genius that people have been Tweeting their favorite stories about meeting the comedian over the decades. The Conan appreciation is deep.

Here’s mine.

The Executive Offsite

In 2019, I was the EVP of marketing for a division of WarnerMedia, which was just being acquired by AT&T.

All the top-ranking execs were invited to a lavish three-day media event at The Ritz-Carlton Bacara in Santa Barbara, CA.

Somehow, I made the list.

They rented the whole place out for a couple hundred people.

The entire resort.

Fancy meals and activities. Sessions and experiences. Massages. Whiskey tasting. The gift bag in my hotel room included a $150 windbreaker, automatic gold status on American, and lots of bespoke goodies.

Like Jurassic Park, they spared no expense.

The guest speakers were incredible. Arianna Huffington, Megan Rapinoe at the height of her World Cup fame, Charles Barkley (I think?), and many executives and talent from the WarnerMedia ecosystem of companies (Turner, Warner, HBO, DC comics, etc.).

I was excited about the final event of the offsite—an intimate Q&A with Conan.

The only problem is that this was an event full of busy execs with large expense accounts, so by the final day’s morning, almost everyone had left, whisked away to private flights and helicopter rides back to LA.

So when I arrived to the ballroom for Conan, there were only 50 people in a room made for 500.

The staff clustered us close to the stage and turned the lights low, hoping that Conan wouldn’t notice. After all, he was billed as The Big Closer of the extravagant week.

They announced his name, and he walked out to the sound of tepid applause. We did our best, but the giant ballroom swallowed up any volume we could muster.

The look on his face when he walked out was priceless, and he called it out immediately. It was clear that this audience was not what he was promised.

“Please don’t get up,” he quipped.

He still delivered a fun, honest, high-energy conversation and stayed to talk to people for an hour.

No hint of disappointment or ego bruising.

Quite the opposite. Earnest gratitude and joy to meet people who simply worked for the same conglomerate media company as him. He called everyone co-workers.

I got to shake his hand and say that I liked his (then brand new) podcast Conan O’Brien Needs a Friend.

That must have inspired him to ditch the TV show and focus on it. #YoureWelcome

I already had a framed quote on my wall — his famous “Work hard and be kind” motto that became famous after his unceremonious exit from his dream, The Tonight Show.

But this experience made me a lifelong fan.

The Expectations Game

Conan could have been annoyed.

I know I would have.

It reminds me of another video that made the rounds a month ago.

NVIDIA has had a great year. The microchip manufacturer that has slowly grown over the past few decades, but in the last six months has grown to be worth $2.2T (that Trillion).

Its CEO Jensen Huang delivered this speech—in a season of endless tech industry praise—to Stanford students:

From the transcript:

“One of my great advantages is that I have very low expectations.

Most Stanford graduates have very high expectations. And you deserve to have high expectations because you came from a great school. You were very successful.

[But] people with very high expectations have very low resilience.

And unfortunately, resilience matters in success.

I don't know how to teach it to you, except that I hope suffering happens to you.

I was fortunate that I grew up with my parents providing conditions for us to be successful, but there were plenty of opportunities for setbacks and suffering.

Greatness is not intelligence. Greatness comes from character and character isn't formed out of smart people. It's formed out of people who suffered.

So that's it. I wish upon you ample doses of pain and suffering.

This speech has pierced my soul the past few weeks.

Can’t. Stop. Thinking. About It.

I have let high expectations get the best of me.

Thought too much of my talents.

Thought too highly of my story.

“Why isn’t this working? Don’t they know I’m special?”

[insert writing, stand-up, parenting, business, investing, friendships, etc.]

Discouraged when my unrealistic expectations aren’t met.

So I’m attempting to take this advice to heart, and learn the Conan way.

Work hard.

Be kind.

Keep expectations low.

Here’s hoping I’ll be delighted by the results.

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Thanks for reading.

Have you ever met Conan? Or someone like that who impressed you?

Never meet your heroes, I know.

If this one spoke to you, maybe you’ll dig my old post, “Give Up On Yourself.” I’m examining my self-identity and recalibrating self-worth.

You know, real HILARIOUS (but important) stuff.

Or maybe you’d like to revisit the 13 things I wish I would have known when I sold my advertising agency.

If that’s your bag, you might want to sign up for a founder’s cohort I’m starting up this spring. Something I’m calling Good Misfortune. Fill out the interest form here.

Have a great week — go get ‘em.

Alec