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Of Being Barack Obama’s Deputy Chief of Staff and Having Tummy Troubles on Air Force One

I’m a sucker for books by successful women who are open to sharing the ups, downs and everything in between their journey.

Alyssa Mastromonaco was Deputy Chief of Staff to US President Barack Obama, and in her book Who Thought This Was a Good Idea, she shares her journey navigating the world of politics first as then as Assistant to the President to Deputy Chief of Staff.

In a nutshell, her job was a combination of knowing something (much more than most people I know) about everything with which Obama had to deal while managing the logistics and sensitivities of his schedule as well as that of other critical decision makers at the White House. Who Thought… focuses on the people with whom she worked, challenges and successes during her tenure, some “personal shit,” and the lessons learned — both what to do and not to do.

The title of the book is a question that was most often posed to Obama during his tenure as USA’s Chief of State.

Mastromonaco‘s stories and narrative give you a sense of the breadth of her work – it is staggering. She handled Obama’s campaigning and took on large responsibilities such as being on top of the ins and out of the President’s schedule, handling national and international issues. Her experiences are riveting. She was in Haiti to witness the aftermath of the 2010 earthquake. She recounts practising kindness and humility as she watched many others do, making mistakes, and struggling like the all of us do while straddling a demanding job and a social/personal life.

Through the book, Mastromonaco takes the reader into the world of politics with some heavyweight names and notable incidents. Some critics have complained about the lack of detail on her work and the politics of the time. However, a lot of information that she was privy to, as it was and still is confidential, and revealing it would have irresponsible.

Rather, it was the relatable moments in Who Thought… that hooked this reviewer. Mastromonaco writes about going to work on Airforce One and being close to Mindy Kaling or Anna Wintour, and it would be intimidating but for her confession about having tummy troubles during stressful situations. Who can’t empathise with that?

My favourite part of the book is about her move from the White House to a non-political stint as COO at Vice Media – she talks about her decision-making process, the emotional roller-coaster and finding her voice and place away from a team she’d worked with for over a decade.

There is a lot to take away from this book, from what to do when making a career shift – don’t do it on your own, talk about the decision with other people whom you trust, it’s a long process, be kind to yourself, and accept that there will likely be rejection (from either end) before you find what you’re looking for, and more.

The book was a quick read and gave this reviewer insight into what political life entails, but mostly it was a reminder that working hard, not taking yourself too seriously, being kind to others, and believing in yourself makes for an exciting and meaningful existence.

My favourite line from the book: “Learning how to become a decision maker, and how you ultimately justify your choices, can define who you are.”

Aren’t all of us trying to figure out this definition for ourselves?



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