Former White House speechwriter on working for Obama, joking about Trump and his new book For David Litt, the journey to presidential speechwriter began in unlikely ways.

 -- There is no one path that leads to a job as a presidential speechwriter. But for David Litt, the journey began as a young man growing up on New York City’s Upper West Side with aspirations for a career in comedy.

“I did stand-up comedy at the school talent show ... and it didn’t go terribly,” Litt told ABC News' "Uncomfortable." “I would say I was the best, ninth grade, stand-up comic at that talent show.”

His career turnaround came on Jan. 3, 2008. Then-Sen. Barack Obama delivered his Iowa caucus victory speech. Litt said he watched on cable news aboard an airplane. “They said our sights were set too high. They said our country was too divided,” Obama said. “We are one people. And our time for change has come.”

Litt was hooked. “Within two minutes I was like, ‘OK, whatever that person is doing I want to be a part of that,’” said Litt. “And by the time we landed, I was one of those people that would not shut up about Barack Obama.”

Litt worked his way up in political circles, from campaign volunteer and organizer to Washington, D.C., intern to speechwriting apprentice. When a series of breaks through his network of contacts landed him inside the White House, a 24-year-old Litt found himself writing speeches for the president of the United States. His new memoir, “Thanks, Obama: My Hopey, Changey White House Years,” documents some of his strongest memories from his time working for President Obama, often in hilarious fashion.

“On some level, the entire country, the most powerful country on earth is counting on you not to screw up in some small way. And that’s a weird feeling because you’re also just a human being,” said Litt. “I think my way of trying to make sense of it, or at least with it, was to kind of laugh at it and enjoy it.

“That’s one of the reasons I wrote the book I did because I felt like I am totally fine telling stories where I do something dumb. In fact, those are my favorite stories.”

During our conversation, Litt opened up about the stories behind some of those anecdotes: his first speech written for the president (he got slammed), his first time working with an entirely female team (“What I did feel was, ‘Oh. I noticed this.’”), his reaction to seeing Obama roast Donald Trump in his 2011 White House Correspondents' Dinner speech, (“I remember thinking, ‘That’s the end of Donald Trump.’”) Litt, now head writer for Funny or Die, also discussed the deliberate efforts made to diversify White House staff, the very real racism he witnessed on the campaign trail and throughout his time with the administration, and how he views the current political climate as an outsider to the system.

“No matter how dark and depressing it gets sometimes,” said Litt, “we will get out of it. It’s just going to take a little while, but this isn’t going to be like this forever.”

Check out the full conversation on this week’s episode of "Uncomfortable."

Download and subscribe to the "Uncomfortable" podcast on Apple Podcasts, Google Play Music, Stitcher, and ABC News podcasts.

Litt was interviewed as part of a series called "Uncomfortable," hosted by Amna Nawaz, that offers in-depth honest conversations with influential figures about issues dividing America.