The title of Alyssa Mastromonaco’s memoir is taken from a question often posed by Barack Obama, when she was the White House deputy chief of staff (making it on to the list of “Washington’s most powerful, least famous people”). The cover photo features Mastromonaco sitting on Air Force One, with the first African American US president lolling casually beside her.
However, what looks set to be an insider narrative on the Obama administration soon emerges as what Mastromonaco terms an “advice book/memoir geared towards women between the ages of about 15-25”. This is an approach that, while valid in its own right (Mastromonaco, now in her 40s, is an engaging, vivid narrator), is frustrating when it comes to delivering real insights on either the Obama presidency or the man himself.
Mastromonaco (who later worked at Vice Media, as did her co-author, Lauren Olyer) joined Obama after stints working with Bernie Sanders and John Kerry, and she certainly comes across as proficient. The book is a blizzard of events and troubleshooting, with detailed (sometimes overdetailed) descriptions of her duties. Her accounts of disasters (Hurricanes Katrina and Sandy; the Haitian earthquake) are riveting, as is the lead-up to Obama’s inauguration (Mastromonaco likens it to being “a bouncer at an exclusive club in New York”). Elsewhere there are intriguing details, such as how the West Wing is as brightly lit as a television studio (because television crews needed to film there). Moreover, one can only applaud Mastromonaco for getting the first tampon dispenser installed in the West Wing.
Obama, one of the most compelling figures of our era, drifts through the book rather like an amiable ghostHowever, throughout the book (which has been optioned for a TV series by Mastromonaco’s friend, comedian Mindy Kayling) there’s a constant glut of high school-level “oversharing”. We hear about Mastromonaco getting her period at a state dinner, suffering from diarrhoea at the Vatican (Mastromonaco has IBS), being excited to visit Buckingham Palace, feeling sick on a helicopter, splitting her trousers, getting married, suffering from infertility, moving house, and so on. It all gets a bit “Dear Diary”, giving the book a dated “Bridget Jones in the Oval Office” feel.
Indeed, while it’s great that Mastromonaco is, say, so open about suffering from professional stress (a welcome counterpoint to macho grandstanding in workplaces everywhere), the endless personal details eventually start to feel like filler. As does the “advice” element of the book, which basically amounts to: “Work hard. Be organised. Be nice.”
Ultimately, you wonder if all this (and the self-imposed “15-25” reader bracket) is to distract from what’s not being delivered: namely, the lowdown on working closely with President Obama. As it is, Obama, one of the most compelling figures of our era, drifts through the book rather like an amiable ghost – sympathising with Mastromonaco about her dead cat, congratulating her on doing sit-ups, gossiping a little about her love life… and that’s about it. While political memoirs shouldn’t revolve around “dishing dirt”, this is too antiseptic.
Towards the end, Mastromonaco all but admits that she doesn’t feel able to disclose certain details or stories, and that, in the future, she may wish to work again in politics (so presumably she doesn’t wish to be known for talking about Obama).
Ultimately, maybe Mastromonaco felt that she had no choice but to self-muzzle, keeping Obama and his administration at (sainted) arm’s length, making what could have been an intriguing memoir something of a disappointment. It says it all that, ultimately, I ended up liking Mastromonaco (warm, smart, nice) rather more than her book.
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 is published by Little, Brown. To order a copy for £12.74 (RRP £14.99) go to bookshop.theguardian.com or call 0330 333 6846. Free UK p&p over £10, online orders only. Phone orders min p&p of £1.99
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