Being Obama’s right-hand woman, aged 32 

Alyssa Mastromonaco's new memoir, recounting her time in the White House, is a fascinating insight into the corridors of power. It also proves that young, Veep-watching, cat-loving, wine-drinking, foul-mouthed women can make it to the very top

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By Marisa Bate on

“When you see my life on paper, it’s not remotely obvious how I would end up, at age 32, working as the right-hand woman to the first African-American president.”

This is the start of Alyssa Mastromonaco’s memoir – the story of how an ordinary woman landed an extraordinary job.

To qualify “ordinary”: Mastromonaco really loves her cats; she swears like a trooper; she loves Scandal and Veep (even though she has worked in the *actual* White House); she gets really excited when a man she fancies emails her, and uses loads of exclamation marks “!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!”; she’s hilariously open about her IBS – especially that time she met the Pope and was faced with either missing her slot or “pooping on the Pope” (fortunately super strong drugs found at the last moment provided a third option of meeting the Pope, poop-free); as a teenager, she packed groceries and she was, in her own words, “a public school kid from upstate New York with no connections and no Ivy League acceptance letters, who spent more time at God Street Wine shows than in academic club meetings”.

So, yes, “ordinary” in the sense that she is hugely relatable and not at all privileged. But her career – to this point – has been extraordinary. And, no, this is not a Netflix trailer or any film from the early 2000s – loveable, calamitous, single young woman lands Big Important Job and meets the love of her life – this actually happened. (Plus, she’s fiercely intelligent, something women in film aren’t really allowed to be.)

Mastromonaco is now 40 and her book, Who Thought This Was A Good Idea? And Other Questions You Should Have Answers To When You Work In The White House, is part memoir, part career advice, part drive to encourage more women in government roles. The book is split into chapters that are normally hurdles for women in the workplace, such as “Confidence, or the Hope Flood”, “Leadership, or Born to Run Things”, “Independence or You Can’t Just Tagalong”, and “Self awareness, or Are you There FEMA? It’s Me, Alyssa”.

'There were plenty of times when I doubted myself,' she tells me. 'There are times when you're put in a situation and you’re like, ‘Fuck, can I handle this?'


As you can tell, Mastromonaco is funny and the story of a lost graduate working in finance, before getting an internship with Bernie Sanders and eventually working with Barack Obama, is brought to life with charming anecdotes about the potholes of being young and broke in New York. But it’s not all Central Perk and good times. Mastromonaco is a realist. With the book, she tells me on the phone from that same city, “I wanted young people, especially woman, to take away that there is always hope, that you should never give up, you should really identify what it is that you want and keep forcing for it, but also, if I wanted to be an actress that doesn’t mean I don’t have to fucking pay my bills! You have to do whatever you need to do in furtherance of the cause.”

And Mastromonaco did. What stuck with me – as much as the narrative of normal girl gets huge job at ridiculously young age – was how hard that girl worked. One anecdote particularly stayed with me. It was around the end of Obama’s first term and no one knew if he would run again. “I became a recluse,” she writes in the book, “and spent a lot of time in my apartment, going over every single thing that I would need to set in motion if Obama came back from Hawaii and said, ‘Let’s do it.’ I had notes posted all over my living room.” The image of a woman’s flat covered in scribbled plans for a decision her boss hasn’t yet made is surely one of absolute commitment.

And that was Mastromonaco’s job – to have every “single thing covered” for Obama and the First Lady, starting as director of scheduling, a role she’d previously had on John Kerry’s presidential campaign, eventually being appointed deputy chief of staff in 2011. This role involved everything, from organising how to get POTUS into Afghanistan during a sandstorm to nominating White House staff candidates, overseeing the White House Military Office and the Secret Service (as well as successfully petitioning to have the first-ever tampon dispenser installed in the women’s toilets). She met the Pope and the Queen, flew Air Force One. She organised the Hurricane Sandy relief effort.

No wonder she needed so many notes.

And she was doing all this in her early thirties.

Did you ever think, "I can’t do this?"

“There were plenty of times when I doubted myself,” she tells me. “There are times when you're put in a situation and you’re like, ‘Fuck, can I handle this?’ Those first times I was on a helicopter to Iraq or the first time I went to Afghanistan, and I have IBS that’s triggered by anxiety and that’s even more anxiety-inducing – I don’t want to shit myself on the helicopter! – those times when I was so out of my element and it’s a huge moment; it’s not like we’re going to have a meeting and talk about something uncomfortable – no, we’re landing in Kabul in the dark and I have to try and not be knocked down by the helicopter blades.”


Mastromonaco gets her eggs counted because a 'friend' makes a 'joke' about it on her birthday. 'Do you know,' a (male) colleague said to her, 'that according to CNN you are of advanced maternal age?' Happy birthday

Clearly, the shit (a separate variety to Mastromonaco’s well-documented IBS issues) got very, very real. One time, Mastromonaco sat at her desk and realised she had been typing but had no idea what she had actually typed. She took herself off to the doctor who told her she needed rest; Obama told her to have a holiday. Eventually, the pressure would cause her to step down and leave Washington. 

A lot of people suggested to Mastromonaco that it was the stress of working endless hours and high, high pressure that caused her to have only three eggs left, when she had them counted, aged 35. 

“Here’s how I look it at it,” she tells me, “there are lots of people with lots of really boring jobs who have stress-related health issues. At least my health issues were related to something fairly cool and epic.”


This is the subject that doesn’t quite fit in Mastromonaco’s book. The chapter called “Some Personal Shit You Should Probably Know About” describes how she faced the inevitable baby question when she hit her late thirties. I tell Mastromonaco I was surprised to see it there at all. Doesn’t it feel a bit sexist to expect a woman to explain herself and her choices? As she writes in the book: “I’m always asked about kids… as a childless 40-year-old woman I’m either supposed to regret not having kids or be entrenched in IVF.” But she’s neither of those things – despite what people think. “It is not some story I contrived late at night trying to rationalise the fact I spent my peak childbearing years meeting foreign dignitaries and helping the United States respond to natural disasters.”

And so it went in the book. “Also”, she tells me, “because we’re in a period where I have so many friends my age who don’t have kids, who aren’t married yet, who are already divorced. I think the world is different now.” It is and it isn’t. Mastromonaco gets her eggs counted because a “friend” makes a “joke” about it on her birthday. “Do you know,” a (male) colleague said to her, “that according to CNN you are of advanced maternal age?” Happy birthday.

If I’ve given the impression up till now that Mastromonaco is some sort of political Bridget Jones, then that’s partly because that’s what she sells in the book. But there are other sides to her – the side of a 32-year-old who can support the president on a world stage 24 hours a day, the side that fundamentally believes in public service and the protocol and systems of the White House with a huge level of respect – something she says the current administration is paying no attention to (“They think they can take shortcuts. They can’t take shortcuts”). And then there’s the side that takes absolutey no prisoners. When we’re talking about fertility, it’s evident there’s nothing “silly” about Mastromonaco: “I think it’s such fucking hypocritical bullshit, the people who come to me, when you’re 39, and are like, ‘You should freeze your eggs”; I’m like, ‘Fuck you’ – my eggs are rotten already and I’m not spending 20 grand to freeze them.”

It’s a pretty remarkable thing, to chat to Obama’s right-hand woman and realise most of your questions are actually about her and not him, but, yes, Obama was amazing, according to Mastromonaco. He was a fair boss, an inspiring leader, a good laugh, “handsome, according to some people”. He tried to fix her up on dates; when she got engaged, Michelle opened champagne on Air Force One; when her beloved cat died, Obama rang her from Air Force One, claiming he just spotted the cat’s spirit pass the window.

Mastromonaco was once named one of Washington's Most Powerful, Least Famous People. The phrase “behind every great man” springs to mind, and we all know too many women have been hidden out of sight by their powerful male bosses. Yet to be fair, I imagine it’s hard for anyone to step out of Barack Obama’s charismatic shadow, nor is it really expected of White House staff.

But this is precisely why Mastromonaco’s book is genuinely important. Who Thought This Was A Good Idea? proves that exceptionally smart, brilliantly hardworking, dedicated “ordinary women”, who swear and drink and laugh and get excited about going on dates, have every right to be at the most important table in the world.

Who Thought This Was A Good Idea?: And Other Questions You Should Have Answers To When You Work In The White House by Alyssa Mastromonaco is out now 


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