Obama’s right-hand woman: ‘I want a giant, beautiful nerd to get heard’

In 2017, Alyssa Mastromonaco published a memoir, Who Thought This Was a Good Idea?, about her time working in the Obama administration. Between 2009 and 2014 she was director of scheduling and, later, deputy chief of staff for operations, two all-encompassing roles that saw her function as the US president's right-hand woman.

Mastromonaco was the first Obama staffer to exit the traps with a memoir. Those expecting a highfalutin career retrospective were in for a surprise, however, as Mastromonaco waxed lyrical about everything from menstrual mishaps to irritable bowel syndrome. ("You would be surprised how many people come up to me in an airport and they're like, 'Oh my God, I have IBS too'," she says.) The book became a bestseller, with the film rights optioned by the actor and comedy writer Mindy Kaling.

She received messages from readers asking her to elaborate on some of the topics she had written about, and others she hadn’t. “I am a very curious person, so I kept a running list of things that people asked about,” says Mastromonaco. “It was enough for another book.”

If Alyssa Mastromonaco was nervous about revealing too much in her first book for fear of embarrassing colleagues, she had no such issue this time

The just-published follow-up, So Here’s the Thing..., is subtitled Notes on Growing Up, Getting Older and Not Giving a Shit. Once again, Mastromonaco writes frankly about her career, politics, relationships, motherhood and, yes, IBS. If she was nervous about revealing too much in her first book for fear of embarrassing colleagues, she had no such issue this time.  “This one I felt much more comfortable letting my truth out all over the place,” she says.

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Born and raised in New York, Alyssa Mastromonaco made her first foray into politics as a college student when she interned with Bernie Sanders. Today, she credits Sanders for holding left-leaning positions on healthcare and wealth inequality long before they became socially acceptable. "Bernie has always talked this talk," she says. "I think the other 2020 candidates who are johnny-come-latelys to his positions should acknowledge that he has had these positions for his entire political career."

After working a number of other jobs, she found her way to John Kerry and landed a gig as director of scheduling on his unsuccessful presidential campaign. In 2004, she worked on Barack Obama's senate campaign. It marked the beginning of a working relationship that would last a decade.

Returning to civilian life after Donald Trump's election, she took top posts with Vice Media and A&E Networks. She now serves as a senior adviser to Naral Pro-Choice America, advocating for women's right to choose when it comes to abortion services, is a contributing editor to Marie Claire, and a contributor to Crooked Media, a podcasting network founded by Obama alumni.

Now 43 years old, she is married with no children. She tackles the latter in a chapter on motherhood and fertility. At 35, Mastromonaco underwent fertility testing, which determined she had a low egg count. She queries why not having children is the only thing she “can’t be 100 per cent sure about”. That uncertainty about motherhood is something she says she hadn’t seen explored before.

“How many times have you seen someone on television be like, ‘You know what? I just don’t know,’” she says. “Because they’re afraid people are going to say, ‘You know, you know in your heart one way or the other.’ Is my ambiguity about having kids because I have taken care of people for so long in my career that I just didn’t have it in me? I don’t know the answer. I think we need to make it okay to say that.”

Elsewhere in the book, she tackles politics and offers her take on the state of the union. As a former White House staffer, she says the actions of the Trump administration are uniquely hard to watch.

“They do not respect the building or the institution,” she says. “They don’t say or pretend they are governing for all of the American people. President Trump routinely says, ‘My voters, my voters, my voters’. That’s the part that is dispiriting at best, and utterly depressing at worst. Every political campaign and candidate needs to ascend in the office, and they have not done that.”

A self-described socialist, Mastromonaco is a staunch advocate for universal healthcare, and aligns herself with the more left wing faction of the Democratic party. Last year, she supported Cynthia Nixon’s bid to become governor of New York. Though the actor was unsuccessful, Mastromonaco credits her with shifting Governor Andrew Cuomo’s positions further left.

That said, she isn’t quite ready to abandon capitalism. “I think there’s a difference – and they have been conflated over here – between capitalism and greed,” she says, decrying the “sell at any cost” stance adopted by gun manufacturers and the pharmaceutical industry. “Capitalism works.”

What are her thoughts on the already crowded Democratic field for 2020?

"I want to see all the candidates put forward their proposals," she says. "I want to make sure that someone who is a giant, beautiful nerd like Elizabeth Warren – who isn't so flashy, but who is one of the most intelligent people on the planet – gets heard as much as someone who is drawing huge crowds at rallies."

More than anything, she hopes that Democratic candidates and supporters steer clear of infighting and keep their eye on the prize. “I hope they keep it cool.”

So Here’s the Thing...: Notes on Growing Up, Getting Older and Not Giving a Shit is published by Little, Brown