Who Thought This Was a Good Idea?
By Alyssa Mastromonaco

reviewed by Thansha Sadacharam

Pages 272

Genre Autobiography

Published 2017

Who Thought This Was a Good Idea?

The Cheat Sheet


like having a drink with a friend

Standout Feature:

truly relatable advice for career driven women

Key Takeaway:

do what you must to ensure you're comfortable

The quick pass: what did you think?

I got through this book pretty quickly. Alyssa is hilarious and relatable, which comes out in her writing style. The book felt like having a drink with a friend, who was telling me about a stressful moment in the day where she’s running around the office looking for a tampon in between meetings. That office just happened to be the White House, and those meetings just happened to be with Barack Obama.

what stood out the most about Alyssa's approach to career advice?

SPOILER ALERT | Real information for career driven women: There was never this “you can have it all, just lean into it”. Alyssa was real about the challenges she had along the way, from dealing with IBS when meeting the Pope, to finding out she had a low egg count and wouldn’t be able to have children. She goes as far as laying out packing lists for business trips overseas, and outlining the various ways she used her calendar to keep her life organized.

“You should always be prepared to defend your choices, whether just to yourself (sometimes this is the hardest) or to your coworkers, your friends, or your 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. Learning how to become a decision maker, and how you ultimately justify your choices, can define who you are.”

Alyssa Mastromonaco

Do you feel Alyssa's sharing of her White House experiences break new ground for aspiring leading ladies?

Definitely–Alyssa is a different kind of brand of career woman. She doesn’t have an Ivey league school on her resume, and her career path wasn’t a clear shooting arrow following her graduation from college. This book opens us up to success that looks and feels different from what we’ve seen in the past for “successful” women.

She illustrates that you don’t have to have a house with a double garage, where your 2.5 children live. That success can be an apartment in the city with your two cats and loving partner, where you don’t know what is next, but you are proud of the relationships you’ve made with the people you’ve impacted.

What was your key learning from 'Who Thought This Was A Good Idea?'

Being as prepared as you can be allows you to focus on the important things that you can’t prepare for. Living in a world that is constantly changing, the demands on us to be able to keep up are always increasing. Alyssa's journeys taught me an important lesson about taking care of the things to make yourself comfortable and safe in order to tackle the ever changing world.

Getting to know the Bad Girl

Thansha is Senior Technical Program Manager at Shopify

How has reading impacted your life?

At three years old, my mom, my sister and I fled Sri Lanka to come to Canada. My parents, like so many others that make up this country, wanted to give us a chance to live in peace and came here as refugees. I went to school being unable to speak English, and struggled to fit in. I wasn’t sporty, and I wasn’t “cool” in the traditional sense of most elementary students.

But I had these magical trips to the library. My mom would walk my brother, sister and I there on weekends, and I still remember how much I loved running through the rows and rows of books. I would proudly exchange the books I read for stickers and new books to take home and read.

At times, reading was my escape. It gave me the ability to explore parts of the world I didn’t understand or couldn’t experience. Eventually I would start writing just as much as I was reading. Reading books taught me how to express what I was feeling in writing. This has helped me process so much as I’ve ventured through my own life.

Everyday I am grateful for books, and my ability to read and write, something I think we often take for granted.

What was the first book that moved you?

Oh god, I’ve been reading and writing for as long as I can remember! This one is tough, probably the Babysitters Club? NOT deep, I know, but I was an immigrant kid trying to fit in, and I loved the idea of a bunch of girlfriends coming together to run their own business, while supporting each other through the ups and downs of everyday life. I see that a lot in my own life now.

“Everyday I am grateful for books, and my ability to read and write, something I think we often take for granted.”

Thansha Sadacharam

Currently on your bedside table:

Know My Name by Chanel Miller

Three books you’d recommend to a stranger:

The Education of an Idealist by Samantha Power
The Bell Jar by Sylvia Plath
Motherhood by Sheila Heti (Still one of my favourite Bad Girl Book Club discussions)

Guilty pleasure book:

Anything Young Adult. I am still a sucker for anything by John Green.

most admired human

My mom and my sister. They are two of the strongest and inspiring women I know.