An Obama Speechwriter On Work, Country, and Getting Things Done in the White House

Book review: Thanks, Obama by David Litt (Amazon / Book Depository)

Few activities offer less upside than a staring contest with the president. But now, having started one, I didn’t know how to stop. I considered averting my gaze, like a shy maiden in a Jane Austen novel, but that would only make things more awkward. I kept looking at President Obama. President Obama kept looking at me. Finally, after what seemed like hours, he spoke.
“What are you doing here?”
…A different young staffer would have handled the situation gracefully…they might have kept things simple: “I’m hoping to catch typos.”
Here is what I did instead. First, in a misguided effort to appear casual, I gave the leader of the free world a smile reminiscent of a serial killer who knows the jig is up. Then I said the following:
“Oh, I’m just watching.”

When former Obama administration speechwriter David Litt’s memoir was published in September, I was feeling a little too burnt out on political topics to read it immediately. To be fair, I’d recently read three books of Trump-related commentary or examinations of the alt-right movement so pessimism seems reasonable.

But this isn’t about Trump, although, being the orange elephant in the room, he’s mentioned and our current view on the presidency versus that of just two years ago is understandably compared. Litt manages to do it in such a way that we can laugh a little at what the office and its administration has become, while still sowing some seeds of hope about the good people who aren’t giving up on the future. Here, he describes the vetting process for hiring:

While the FBI was making sure I wasn’t a threat, White House lawyers were making sure I wasn’t an embarrassment. I write these words during the early days of the Trump presidency, when rejecting unsavory applicants seems as quaint and old-timey as canning your own peaches. But in the olden days of a few years ago, the vetting process struck fear into our hearts.

But it’s not all bad, not by a long shot, actually. This book is different from what I was too tired to read more of; it’s a breath of fresh air amidst the constant bad news onslaught since last election day. The tone is light while still addressing big issues.

Litt began political work as the dreamy-eyed optimist so many of us were back in 2008, and as the reality of his work broke him in, he managed to end the Obama years visibly older, wiser, and bordering on burnt out, but not broken down. His clear, honest depiction of what’s happened and what we’re still capable of is a realistic pick-me-up. Read this together with The American Spirit for some much-needed optimism.

Litt describes how he came to work at the White House (or, at the beginning, close enough) during both of Obama’s terms, working his way sort of haphazardly up the “speechwriting totem pole.”

He started out knocking on doors during the 2008 campaign before working at a crisis management company in DC, then networking to speechwriting, quickly landing the position of Valerie Jarrett’s speechwriter. Later he transitioned to the Obama team. He begins contributing a few jokes to smaller projects, and eventually earns his reputation writing remarks for big funny things, like the White House Correspondents’ Dinner, and big serious things as well.

It’s that proverbial “dream job”, but he gives it the warts and all treatment, showing that it’s far from glamorous and more difficult than one might imagine. He connects his work to the greater issues, marvels at what was accomplished despite obstacles, and tells fascinating behind-the-scenes stories of some of the memorable moments and milestones that he contributed to.

Litt often feels like a fish out of water in D.C. – he’s very young, but so were many Obama administration staffers. A Yale graduate, he’s surprisingly modest and self-deprecating throughout, which is admirable because a few times I sensed this could become uncomfortably privileged. It doesn’t. He acknowledges what he needs to and tells the truth about the rest. Well done.

Behind me, out of the corner of my eye, I could see the Emancipation Proclamation. Not a photocopy or poster. The. Emancipation. Proclamation. I didn’t turn to look at the document, but I could feel the message it was sending through the room.
“I’m here because I freed the slaves,” it seemed to say. “What are you doing here?”

The title comes from a nagging voice he hears when he’s tired, frustrated, overworked:

On cue, Sarah Palin’s voice pops into my head. She’s always doing this, showing up when my spirits are lowest. It’s like I have a fairy godmother who hates me.
“So,” she asks, “how’s that whole hopey, changey thing workin’ out for ya?”

The answer varies. The job has major ups and downs (“Not a moment passed when it didn’t feel as though everything was falling apart”), sometimes he disappoints himself, sometimes he triumphs, ultimately he learns a lot. There are elements of the classic American success story at play, both in his family background and personal progress. He laughs heartily at his mistakes (once any uproar has died down) and is seemingly honest, even when it makes him look mildly incompetent at best, and triggers international incidents at worst.

Also interesting, more than I’d expected, were descriptions of the writing process. He describes the rigid specifications that accompanied each event or occasion, and how the day’s politics influenced language.

A highlight are his interactions with the president. Litt always seems caught at the wrong moment, acts awkwardly, or gets hung up in the decorum that surrounds even a more down-to-earth, personable leader. He demonstrates a lot about the president’s mentality in these little analyses, something that he credits Obama as being adept at. But he’s pretty good at reading people himself. The president came close to having a Michael Jackson Pepsi commercial moment, and he even manages to put that into the context of Obama’s personality and work ethic.

Some favorite quotes, out of many:

Because the correspondent’s dinner played an outsize role in my White House career, I should acknowledge up front that it is bonkers. Imagine learning that once a year the British prime minister leads a mariachi band, or the Chinese premier performs burlesque. Yet in America, tradition dictates that each spring our commander in chief don black-tie attire and perform a comedy monologue in the ballroom of a Washington hotel.

I squeezed against a wall, identifying faces of congressional Republicans like a bird watcher who deeply loathes birds.

At the risk of sounding boastful, I had now gone two full years without angering a sovereign nation.

Ted Kennedy and Barack Obama were wrapping up a week of joint appearances, a political odd couple on the road trip of their lives. It was like watching Julie Andrews and Lady Gaga team up for a Christmas album.

President Obama had not just fixed an economy. He had not just ended a war. He had made America a better place than the one where I grew up. The country I lived in seven years ago, the country I lived in seven days ago, had been fundamentally transformed.

The writing is always smart and hilarious with some very touching moments peppered throughout, in recalling both work and life. The book is sweetly optimistic with an especially uplifting conclusion, which says a lot because Litt is blunt about the particular difficulties that come with government work, especially on this level. This includes the glacial pace of change and the Trump administration’s bull-in-a-china-shop mentality as they charge through rolling back as much Obama-era progress as possible.

But he reminds us there are still good people working tirelessly despite setbacks, despite the fairy dust of the hopey, changey days being long gone.
My rating: 4/5

Thanks, Obama: My Hopey, Changey White House Years
by David Litt
published September 19, 2017 by Ecco

(Amazon / Book Depository)