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Lean In v. Bossypants: Two feminist leadership books


I snapped up Sheryl Sandberg’s book Lean In as soon as the hardcover was published. As an aspiring leader, I was eager to learn from a woman who had climbed to the top in the male-dominated tech industry to become the COO of Facebook. I sat down to the book the way I wanted to sit down at the boardroom table. Wearing sharp high heels, siting up straight, and snapping open my pen, I prepared to get down to business with my new mentor Sheryl.

But I was in the wrong seat. Sheryl was snuggled up on the couch with a cup of tea. She was like the best big sister I never had, encouraging me to work hard and be true to myself. It was very sweet. But it was not what I needed – or wanted. Lean In feels like it’s actually a self-help book, not a business book. It says “Yes ladies, you can have it all!”

Which is bullshit. Everyone has to actively choose whether they are full speed on their career or their family. You can’t do both 100%. This choice must be made by women and men, and there are obviously the traditional decisions: men earn the money and women raise the kids. Going against that trend causes distress. But making the traditional choice also causes stress for dads who wish they didn’t miss so much of their kids’ childhoods and for moms who compensate for their lost professional achievements by creating homemade, organic, sugar-free, craft cupcakes and crying into the icing.

Sheryl’s book, as it attempted to be empowering, was somehow dismissive of the full scope of the struggle that working women face every day. What about the panic you feel when your meeting ran over and you’re going to be late to day care pickup again? What about the selfish dread that creeps up as you are working your day job while your kids cry in that day care? What about the futile cash flow you create by funneling your entire paycheck back into that day care? Let’s face it: Sheryl is an educated white married woman with the privilege and opportunity to Lean In. Meanwhile, almost one year to the day after Lean In was published, a single, black, homeless mother of two was arrested after leaving her kids in the car so she could attend a job interview.

Lean In left me disappointed. I wanted more realistic, aggressive, pragmatic leadership for professional women in the modern workplace.

I didn’t expect to find it in comedian Tina Fey’s book Bossypants.

I picked up Bossypants looking for a quick and easy read over the holiday break, and I’ve been giving copies to all my fabulous female friends ever since. The next text will be just a collection of quotes from the book:

+ “In most cases being a good boss means hiring talented people and then getting out of their way.”

+ “You have to try your hardest to be at the top of your game and improve… until the last possible second, and then you have to let it go.”

+“Don’t waste your energy trying to educate or change opinions… Do your thing, and don’t care if they like it.”

+“Whatever the problem, be part of the solution. Don’t just sit around raising questions and pointing out obstacles.”

+“So, my unsolicited advice to women in the workplace is this. When faced with sexism, or ageism, or lookism, or even really aggressive Buddhism, ask yourself the following question: ‘Is this person in between me and what I want to do?’ If the answer is no, ignore it and move on. Your energy is better used doing your work and outpacing people that way.” +“There are no mistakes. Only opportunities.”

I couldn’t say anything better myself, so that’s all I’ll say about the surprise best business leadership book of the last 5 years. You should buy it now. Now!

For a final exercise, let’s compare the cover portraits: Sheryl is warm and gentle in her white cashmere cardigan. She is polished in a way that says “professional, but friendly.” Her right hand is on her chin as though she’s having the most fascinating conversation with you, dear reader. Tina, on the other hand, is just her woman’s head on a man’s body, complete with hairy arms and silk tie. She’s a comedian, so the picture is offbeat, funny, and a little startling. Her big manly right hand lays against her cheek. She looks a little tired. Or maybe she’s just kind of over-it.

These are the pictures of two women leaders on the covers of their books. And who says you can’t just a book by its cover? Women are judged this way every day.


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