Career advice from a checkout clerk turned Obama sta≠er
Book review by Caitlin Flanagan
We’re two months out from the peaceful transition of power, and right on schedule, here come the staffer memoirs from the Obama White House. Alyssa Mastromonaco — who worked for the president for more than a decade, including as his deputy chief of staff — has written one for a particular audience and with an appealing slant. “Who Thought This Was a Good Idea?” is intended for young people starting their professional lives, and it is a combination memoir and compendium of very good suggestions about how to get ahead — very far ahead — at an early age.
A self-described “townie” from preposh Rhinebeck, N.Y., Mastromonaco worked as a grocery checker in a supermarket, one of many jobs at which she excelled at excelling — loving double-coupon day as well as the Wednesday before Thanksgiving because it “put my bagpacking skills to the ultimate test.” A “good (-ish)” student, she graduated from the University of Wisconsin at Madison and then found work as a paralegal at a Manhattan law firm, a job known for
WHO THOUGHT THIS WAS A GOOD IDEA? By Alyssa Mastromonaco with Lauren Oyler Twelve. 248 pp. $27
neither excitement nor glamour. Yet she vowed to give it her all, leading her roommate to call her the “Super Para,” which she thought at the time was a compliment. After that, she went to work as the assistant to a high-end real estate broker at Sotheby’s. “Instead of mocking his love of luxury property I went with it,” she reports. “I liked making brochures and talking to clients; I had my favorite properties. It was really pretty fun.”
The Sotheby’s experience, to many young, left-leaning job-seekers (in particular those who had interned for Bernie Sanders, as Mastromonaco had), might have seemed so impossibly unhip and 1 percent-ish as to make another year in the childhood bedroom seem preferable. But as Mastromonaco explains, it proved invaluable to her later success. When she decided she wanted to work in politics and interviewed for a staff position on John Kerry’s presidential campaign, she didn’t think she had much hope. But after her interview, she overheard someone talking about her: “She worked at Sotheby’s — she must be good,” which leads her to impart an important piece of advice about work: “Forward motion is always better than no motion.”
So it is that our heroine goes from the checkout aisle of a Rhinebeck supermarket to the indescribably mismanaged Kerry campaign, then to Obama’s finely tuned Senate office, then to his presidential campaign, and then to the White House — and to what our author might describe as a “s--- ton” of responsibility.
And now: a word about the tone and style of the book. Among the many celebrities she met during her White House years, one who became a close friend was Mindy Kaling, whose two very appealing books — “Is Everyone Hanging Out Without Me?” and “Why Not Me?” — seem to have been major stylistic influences. While there is a strong, feminist “own your own power” through-line, there is also a clear intention to present herself as a cheerful, chubby everygirl. She is part Moneypenny (her chaste, consuming ardor for her dreamy boss), part unembarrassed oversharer (splitting a skirt with her “fat campaign ass”), part always-the-bridesmaid (her live-in boyfriend has three life rules: rent, don’t own; no pets; and never get married). There is also a good bit of information about her mishaps with irritable bowel syndrome. We are not in the hands of Jane Austen; but Jane Austen never wrote a book advising young people to treat all informational interviews “as the real deal, because you never know,” which is why I pre-ordered a copy of this book — and not “Northanger Abbey” — to give to my teenage sons. (It’s intended for young women, but anyone who wants to tell young people that “hard work and a good attitude can take you further than you could ever dream” is getting my 27 bucks.)
Mastromonaco (who wrote the book with the help of Lauren Oyler, who offered “a millennial POV”) is a woman of great achievements, and although she is committed to the cartoon version of herself, she makes no pretense of hiding her accomplishment. During her White House years, she had two secure phone lines in her apartment; the White House response to Hurricane Sandy required her to “become a quasi expert on transportation infrastructure and refined fuel in a handful of days”; and her assessment that she was “helping run the country, in a small way” is patently true. She was included on a list of “Washington’s most powerful, least famous people.” Throughout her tenure, she had to wrestle with something most people at the start of their careers do not: the particular complexities of holding “such a weighty job when you’re really young.”
This may be a story of career success and empowerment, but like more conventional girl books of yore, it has a marriage plot. Her reluctant boyfriend finally surprises her with a proposal, and the next day, in true rom-com fashion, she is sharing a champagne toast with Michelle Obama on Air Force One. Not long after, she resigned from the high-stress job, and her teary farewell — to the president and to the White House itself — is moving.
I read the book on the day the world was treated to photographs of Kellyanne Conway kneeling on a couch in the Oval Office, knees partly splayed and spiked heels digging deeply into the brocaded fabric, her eyes on her ever-present iPhone and not on the group of presidents of historically black colleges and universities who had been invited to meet President Trump. Mastromonaco’s guidebook/ memoir has a powerful if unplanned secondary theme: the profound respect that the previous administration held for the office of the presidency and for the White House itself. On her first day’s orientation in the building, Mastromonaco and a co-worker are taken to see the Oval Office: “The door was open, but we were so nervous we just stood there at the threshold. We were being such tools, but we knew no other way to be. Finally, they coaxed us in,” she says. “The wallpaper is the best wallpaper you’ve ever seen; the artwork would be in a museum if it weren’t in the White House; the desk is the president’s desk.”
No one was jabbing heels into the furniture, no one was sending out a press secretary to lie about crowd size, no one was parking HarleyDavidson motorcycles on the front yard. “He never yelled or demeaned people,” she writes of Obama; his most common way of expressing displeasure with a staffer was a raised eyebrow. Goodbye to all that.
Alyssa Mastromonaco, second from left, served as deputy chief of staff to President Barack Obama. The first time she saw the Oval Office, she writes, she was too nervous to go in.