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BOOK REVIEW: 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 with Lauren Oyler

| 13 November 2017 | Reply

BOOK REVIEW: 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 with Lauren Oyler

Little, Brown
August 2017
Paperback, $29.99
Reviewed by Steph O’Connell




In HQ we occasionally had ideas that were a little campy or aggressive, but we weren’t the ones who had to answer to Obama’s disappointed face when he turned to them and said,“Uh,who thought this was a good idea?”
Shortly after that happened,I would usually get an email from Marv or Reg or Gibbs relaying the question. They would know full well it was me,but it was a gentle—or passive-aggressive—way of calling me out.

Alyssa Mastromonaco worked for Barack Obama for almost a decade, and long before his run for president. From the then-senator’s early days in Congress to his years in the Oval Office, she made Hope and Change happen through blood, sweat, tears and lots of briefing binders.

But for every historic occasion – meeting the queen at Buckingham Palace, bursting in on secret climate talks, or nailing a campaign speech in a hailstorm – there were dozens of less-than-perfect moments when it was up to Alyssa to save the day. Like the time she learned the hard way that there aren’t nearly enough bathrooms at the Vatican.

Full of hilarious, never-before-told stories, WHO THOUGHT THIS WAS A GOOD IDEA? is an intimate portrait of a president, a book about how to get stuff done, and the story of how one woman challenged, again and again, what a ‘White House official’ is supposed to look like. Here Alyssa shares the strategies that made her successful in politics and beyond, including the importance of confidence, the value of not being a jerk, and why ultimately everything comes down to hard work (and always carrying a spare tampon).

Told in a smart, original voice and topped off with a couple of really good cat stories, WHO THOUGHT THIS WAS A GOOD IDEA? is the brilliantly funny, frank and inspirational memoir from a savvy political star.


As an Australian reader who has always felt a certain level of disinterest or disconnection when it comes to politics, especially American politics, I am not the person you would usually call upon to read a politically themed memoir.

But the truth is, Barack Obama’s personable nature over the last eight years has softened my resistance somewhat, and recent events have made the American political scene hard to look away from. Not unlike a very slowly moving car crash.

So I stepped outside my comfort zone of preferred genres and topics and decided to give this one a shot. And I found it quite an enjoyable and humorous read!

Barack Obama was on TV being smacked in the face by sleet. So much worse than snow. Basically worst-case scenario.
We watched (in horror) as the event drew to a close, and Obama reached his hand to Reggie. As we were turning off the TV, my phone rang.
“Alyssa, it’s Obama.”
“Hi!” I said, with my head down on the desk, girding myself for the inevitable and deserved. “The event looked AWESOME! You heard John McCain canceled all of his events, right? He looked like a total old man!”
“Alyssa, where are you right now?”
I was not sure where he was going with this, but I knew it was somewhere bad. “My desk,” I replied cautiously.
“Must be nice.”

This book offers up some great anecdotes about Mastromonaco’s relationship with Obama.

Obama also enjoyed gossiping about my dating life (or lack thereof). At an event at Lawrence Bender’s house in Los Angeles, Gibbs and I were sitting in the den reading our BlackBerries when Obama came over and told me that he had “found someone” for me and that I should “get off the couch and come be social.”

And working with Bernie Sanders.

Sometimes he asked about my family, and where I was from, and explained to me what was going on in the world. I once tried to impress him by telling him about the time my friends and I had climbed on Newt Gingrich’s car. Bernie was unmoved; his attitude was basically, “Well, what else would you have been doing?”

It should be noted that this isn’t a book entirely about Obama and experiences in the White House and politics, though there is plenty of that.

Developing self-awareness is a lifelong process; you don’t just wake up one day and have all you need. So even though I’d spent the last few months demonstrating that I was capable and knew what I was doing, this was something of a revelation. When the president of the United States tells you your words are powerful, it can be pretty shocking. I honestly didn’t think anyone would give a shit if I sent a snippy email.

But rather about Mastomonaco’s own journey, transitioning at a young age from only-child to older sister; through working for various senators and, of course, Obama; to life after the White House; her relationship with a Hurricane Katrina surviving cat; and dealing with the presumption that, as a woman, she must have a deep-seated need to bear children.

At panels for women in government or women in media or any other type of panel that I might be on (it’s usually about getting more women represented somewhere), I’m always asked about children. Do I feel like I sacrificed having kids to pursue my career? Was it hard to make that choice? What do my parents think? And when people finally seem to have exhausted this invasive line of questioning, they add, “Are you sure?” As a childless 40-year-old woman, I am either supposed to regret not having kids or be entrenched in the expensive and often disappointing process of IVF.

Inside, readers will find tips on preparedness, packing for travel, interview techniques, and other little bits and pieces for life, ambition, and womanhood.

On my first day, a woman from Human Resources took me to my desk, and I saw that it was a desk among many desks that sat outside offices, like in Mad Men. You never want to be able to compare your work environment to Mad Men. As in Mad Men, all the desks were occupied by women. Some very simple but useful advice: Always ask to see where you’ll be sitting.

And her experiences travelling with an irritable bowel.

This kind of thing really breaks down barriers with people. When you tell someone, “Here’s the thing: I might have to shit on this helicopter,” and they don’t shun you afterward, you have a friend for life.

And the kind of embarrassing moments we all experience, but about which we very rarely speak.

There are moments when you catch yourself wondering how you look walking off Marine One—wind blowing in your hair, serious leather bag at your side, adjacent to the man who runs the country. There are also times when you actually walk off Marine One with the president on a Friday afternoon in rural Virginia, climb into your armored Suburban, and are told by a member of the medical team that you have split your skirt clear up to the zipper. Those are the moments you should remember: when your coworkers are rallying around you to keep you from showing the president your really old Hanes Her Way underwear.

The book is a no holds barred, conversational, upbeat, and far-reaching memoir, albeit one with many anecdotes involving various politicians, as so many of Mastromonaco’s years until now have been spent in various political roles.

The one major issue with this book is that it is told out of order, leaving readers displaced often when moving back and forth through time so suddenly. These are things Mastromonaco would find easy to jump between, and this way of structuring the story is something Mastromonaco cites as helping to break through the writer’s block (of sorts) that she was struggling with. But we who did not live through those same events can’t help but feel a little lost in time. Are we reading about Obama when he was president or senator? First term or second? 

It wouldn’t be chronological—because to me chronology seemed too much like you were trying to leave your legacy—but instead would be organized by qualities that have helped me in my career: leadership, preparedness, resilience, etc.

That being said, if a reader is happy to go along for the ride and not get too caught up in the details of when and where, this can be read and enjoyed by even those with limited American political knowledge.

The book was originally intended to come out around the end of Obama’s second term, but recent events have shown that it’s bound to resonate even more solidly in the Trump Era, as each news story makes us wonder what on Earth is going on in America right now.

In the days after the 2016 election, several former Obama staffers expressed the sense that, after they left the White House, they had believed they could just kind of fade away into the background of the political sphere, popping up as a surprise debate practice partner or podcast guest when it was convenient or fun. The results made it clear this was not the case: We will have to be active, resourceful leaders of a new movement.


Category: Book Reviews, Other Reviews

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