Sunday Book Club: “Who Thought This Was a Good Idea?” by Alyssa Mastromonaco

Alyssa Mastromonaco is under the impression that Barack Obama did not like her very much when she interviewed for him in December 2004. Mastromonaco heard about a position in Senator Obama’s team from colleagues who she worked with on John Kerry’s presidential campaign. Lesson number one: your network is your most valuable asset. Getting a job in so many cases is about who you know as much as what you know. We are not talking nepotism, though. A diverse network of contacts is like a safety net. I had a very unpleasant work crisis last year, and it was a colleague and friend from my very first job, who lent me so much of her sanity, I did not even need a shoulder to cry on. Sure, families matter a lot, but if you want someone who just gets it about work and your specific career issues, reach out to people swimming in the same ocean.
Mastromonaco did get a job in the then-senator Obama’s office. In the decade that followed, she served as assistant to the president and director of scheduling and advance at the White House, and then as assistant to the president and deputy chief of staff for operations at the White House until 2014. She was the youngest woman to hold that position. As part of her job, she coordinated logistics and operations of two presidential campaigns and inaugurations, devised plans for recovery during natural disasters, including floods and hurricanes, oversaw Obama’s foreign travels, including his trips to Afghanistan and Iraq, and so much more. This year, Mastromonaco published a book, reflecting on her experience and lessons learned. Her main goal was to get more women interested in and excited about working in government. As she admits, there never was a woman from the White House who had written such kind of book before. The lessons Mastromonaco shares could be useful to anyone in any industry.

Lesson Two: Be always prepared to defend your choices, whether just to yourself or to your coworkers, friends or family. “The quickest way for people to lose confidence in your ability to ever make a decision is for you to pass the buck, shrug your shoulders, or otherwise wuss out.” 

Mastromonaco gave insight in what it was like having Obama as your boss. The book is generously peppered with most amazing stories. As you might have guessed, Barack Obama is not someone who makes you feel small; there is no external pressure to make you take shortcuts. He assumed his team were adults and learned their own lessons when things did not exactly go as planned. 

Lesson Three: Do as much research as you can and keep your ears open. You will learn a lot about yourself by being open to hearing feedback. 

Lesson Four: The importance of self-awareness – knowing when you are at your best, what you are like on not so good days, and how much sleep you need to function without snapping at people – will allow you to keep your contacts, reputation and sanity throughout your career. Developing self-awareness is a life long process. Just stop and listen to yourself from time to time. In return, your mind and body will give you their optimal performance. 

Lesson Five: Know when it is time to leave. Mastromonaco left the White House when she reached the level of exhaustion, nervousness and insomnia that was beyond coping. We all have different reasons to say “that’s enough.” The point is, do not overstay when you know it is hopeless. I firmly believe that as we only have one life to live, we must make the most of it. Surviving in a place you hate is never a way forward. Remember, self-awareness.

Lesson Six: Know your worth. After leaving the White House, Mastromonaco accepted a job offer from VICE, where she had to negotiate her salary. Her advice: if a potential employer asks how much you want, the best response is “I’m sure there’s a salary band for the position, and my hope would be to come in at the high end of that.” For some of us, money talk will never be easy, but this is a diplomatic way to show that, as far as you are concerned, you deserve the best in your league.

Lesson Seven: Never underestimate the importance of kindness, which extends beyond “please” and “thank you.” Mastromonaco put it brilliantly: “Working in the White House is obviously heady, but it is also humbling – you are around the most brilliant, decorated brains in the country, that do not have to do anything for you, but they often do. If you approach it with grace – and a willingness to accept that many people know much more than you – you can walk away a much better person than you were when you came in.” 

At some point in your career, you will be the youngest, the oldest, the newbie, and, if you stick around long enough, the most experienced person in the room. How exciting is this! Nothing is truer than an old adage: “love what you do, and do what you love.” 

I considered keeping this book in my personal library. However, it is too good not to be shared. Therefore, as most of my books, I will be donating it to Oxfam, so it can inspire someone else.