Entrepreneurs

David Litt became a speechwriter for President Obama at 24—here’s how he found the confidence to do it

The first time David Litt met his new boss in person, he blacked out.

Litt, then 24, had just landed a gig as a speechwriter at the White House. His boss was President Barack Obama.

Obama asked Litt, "How's it going?"

"And I have no idea what I said. I could have said anything. I assume it wasn't that bad because I didn't get fired, but I have literally no memory of what happened after that," Litt tells CNBC. "And I later talked to other people and that's a fairly common occurrence upon meeting a president — you just totally freeze like a deer in the headlights."

Litt, now 30, was one of the many millennials who became obsessed with Obama when he heard the then Senator campaigning.

David Litt with President Obama and Keegan-Michael Key.
Photo courtesy David Litt
David Litt with President Obama and Keegan-Michael Key.

After graduating with a degree in history from Yale in 2008, Litt drove to Ohio and worked as a field organizer for Obama. "And then I moved to D.C. with absolutely no plan whatsoever and was lucky," he says.

Litt landed an internship in D.C., though that didn't go terribly well.

"I was the world's worst intern at a communications firm. I almost got fired more than once, and it definitely did not bode well for my future job prospects," says Litt.

"Without knowing that such a thing existed, I ended up at a White House entry level speech writing job." -David Litt, former speechwriter for President Obama 

"But just through a friend of a friend, right as this one internship was collapsing another internship door opened, and so I ended up working at a speech writing firm called West Wing Writers," he explains. "They wrote speeches for Senators, C.E.O.'s everyone in between, heads of big foundations, and that's how I got to learn some of the craft of speech writing."

Two years later, Litt was hired to be an entry level speechwriter at the White House for Valerie Jarrett, then the President's Senior Advisor.

"Sort of without knowing that such a thing existed, I ended up at a White House entry level speech writing job," says Litt.

He can still remember the first time he wrote words that the President of the United States spoke out loud.

David Litt

"I was 24 and he was in San Juan, Puerto Rico, and it was just a short stop at the airport, so for people who have been writing speeches for a long time this was not a big deal. For me it was the biggest deal that had ever happened ever, obviously," says Litt. "It was almost surreal. I was watching on the livestream and it was just this very strange thing where you're like, 'I had some of these thoughts and now they are leaving the mouth of President United States.'

"It was totally bizarre and even more bizarre was that Jon Stewart made fun of that speech that night on 'The Daily Show.' That was the moment when I was like, 'Wow … My high school self is totally confused by what's going on,' because, you know, Jon Stewart just made fun of something I wrote on television."

Litt did very well in the job he hadn't even known existed.

For his first two years, Litt's official title was "Speechwriter." In 2012 he was promoted to Presidential Speechwriter and in 2014 to Special Assistant to the President and Senior Presidential Speechwriter. He was also the lead joke writer for the four White House Correspondents' Association dinners during his tenure.

David Litt with President Obama
Photo courtesy David Litt
David Litt with President Obama

In January 2016, Litt stepped down to take a job as the head writer and producer for comedy website Funny or Die in its Washington, D.C. office. Now he's also writing a memoir of his years coming of age in the White House, "Thanks, Obama: My Hopey, Changey White House Years," due out in September.

Litt started his career at the White House very young, but he wasn't the only one. "There's lots of young people there because you work incredibly long hours, nobody's paid very much, and so young people are often the ones with the energy to do that kind of work," he says.

And generally, Litt was measured by the quality of his work, not his age. "The truth about working in the White House is it's so stressful and high pressure that if you can make it, it doesn't really matter whether you're you know the right age or whatever else," he says.

"Confidence is not necessarily organic. You have to have a sense of believing in yourself, but you also need other people who believe in you." -David Litt, former speechwriter for President Obama

"Once you demonstrate that you can do the work, people really gravitate toward that, and so that was a big part of why it was possible for me and other people my age to really succeed at the White House. I think particularly because President Obama was young and had a young staff, people understood that."

Even still, it took Litt some time to develop confidence in himself and in his abilities. That came with experience and the trust of his very capable colleagues.

"Confidence is not necessarily organic," he says. "You have to have a sense of believing in yourself, but you also need other people who believe in you — and are better than you are at whatever it is you want to do — but have faith that you can get good at it as well. And I think that's what I was lucky enough to have both in the private sector and then in the White House."

David Litt with Airforce One

When Litt did find himself doubting his abilities or was particularly frustrated by a long day or a rejected draft, connecting to the larger purpose of why he was doing what he was doing always propelled him. He had a poster that all of the field organizers he'd worked with in Ohio gave to him that he would look at for inspiration.

"A lot of the time you keep going because you don't really feel like you have a choice. And that ends up being what courage looks like more often than not." -David Litt, Funny or Die writer

"It just connected me back to that original idea that got me involved with the Obama campaign: faced with impossible odds, people who love this country can change it," says Litt. "And knowing that this wasn't about me and there were people all over the country who were part of this movement and cared about what we were doing, that made it a lot harder to decide to give up and so then you keep going."

And finally, sometimes you find the capacity to rise to the challenge because you have no alternative, says Litt.

"A lot of the time you keep going because you don't really feel like you have a choice. And that ends up being, you know — that's what courage looks like more often than not.

"And so one of the things that I learned from President Obama ... is perseverance," says Litt. "I mean, he went through any number of moments when the wider world said his presidency is over, he failed and he just kept going, and in the end so many of the successes he achieved were because he didn't quit."

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