Bossypants by Tina Fey9 min read

Last weekend I was staying in a rented cottage and fell upon Bossypants while perusing the quaint library sitting over the old television set. I had heard about this autobiographical book written by Tina Fey of Saturday Night Live fame, but it had not made its way onto my reading list. However, since I didn’t have any other books with me during this trip, I decided to acquiesce to temptation and peruse the book, just for a second, to unwind at the end of the day. Five hours later I had finished the tome and was officially dubbed the worst cottage guest of the weekend for skipping the board games.

Although I wasn’t purposefully vying for this title, Tina Fey’s book was captivating enough for me to accept my fate. In this light, funny, autobiographical collection of short stories, Tina recounts key anecdotes from her life which have defined her thoughts of a variety of subjects such as beauty, romance, nerdism, women leading in the workplace, politics and motherhood. Written in the first person, the chapters read like chronological “best-of” excerpts from a personal journal.

Storyline

Tina Fey draws the portrait of an awkward, young girl living in the outskirts of Philadelphia. She has trouble making friends but is happy-go-lucky regardless and idolizes her father, the kind of man “they don’t make anymore” (Korean war veteran, firefighter, writer and university administrator); the kind of man who washes his car and get dressed up to come get you at the airport. From there, we fast forward to her favorite summer job where she worked in a boutique theater with fellow awkward teens. She finally felt like she had found her place in the world. She contrasts this experience with her first “real job” as a receptionist in a YMCA to explain the motivations behind her discovering improv and joining the Second City sketch comedy group.

Having found her calling, she connects the dots between her start at Second City, her transition to working as a writer on Saturday Night Live (SNL), becoming the producer (“bossypants”) of the cult favorite 30 Rock sitcom and being caught in a media storm when she agrees to appear on SNL to impersonate Sarah Palin during the 2008 presidential election. Although life lessons are peppered throughout the book, it is a this point that Tina Fey shift the focus to “unsolicited advice” as she refers to it. My favorite of which is the following:

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. Then, when you’re in charge, don’t hire the people who were jerky to you.”

Otherwise, my favorite part of the book is when Tina Fey lists the lessons she took away from working with Lorne Michaels, who has been producing SNL since the late seventies. These lessons are described in the context of show business, but I see application well beyond the walls of production studios. Here they are as I recall them:

Producing is About Discouraging Creativity

When leading a group of creatives, it is very easy to get off-track with new, novel ideas and completely miss the mark on initial objectives. In this setting, a leader must develop aptitudes to navigate what is productive vs. unproductive creativity and course correct his team… No easy task. It reminded me of the following Stephen Covey quote: “The main thing is to keep the main thing the main thing.”

The Show Doesn’t Go on Because It’s Ready but Because It’s 11:30

SNL goes live at 11:30 on Saturday nights. Period. This reality needs to be front and center when prioritizing tasks. This reminds me of the famous (or infamous depending on your experience with it…) Triple Constraint Triangle in project management. Perfect is the enemy of excellence.

When Hiring, Mix Harvard Nerds with Chicago Improvisers and Stir

This references the ideal composition of a writing team for SNL. For me, this comes back to being purposeful when building a team. You must ensure that you are not building a homogeneous group when trying to achieve complex objectives as this will get you in thought pattern ruts. However, if you simply hire a variety of different people without thinking about group dynamics this will cause other types of problems. As with lots of things in life, it’s about finding the right balance.

Television is a Visual Medium

In short, looking and feeling like an old wrinkled, dehydrated potato will do more harm to the quality of your work than constantly sacrificing sleep trying to attain perfection. More so on television because people will see your potato skin… Ariana Huffington of the Huffington Post is a big proponent of this as well.

Don’t Make Any Big Decisions Right After the Season Ends

Give yourself time to come down off an emotional high (or up from an emotional low) before making any major life decisions. Make your decision with a level head. Tina hilariously points out that nobody ever follows this rule.

Never Cut to A Closed Door

This refers to production value. Although you can never expect to get to perfection on time-boxed events, there are certain key “quality rules” that must be respected. I certainly see this as applicable to most projects. What are you Key Success Factors? In the context of SNL, one of these “quality rules” is to never cut to a closed door in a sketch. It screams of faulty timing and low production standards.

Don’t Hire Anyone You Wouldn’t Want to Run into in the Hall at 3 in the Morning

I have a variant of this rule which is a bit more severe which is, don’t hire anyone you wouldn’t want to get stuck in an elevator with for extended periods of time. If it’s in a hall, you can always run away… For teams of knowledge-workers, whether that be in consulting, IT, comedy, etc., rigorous open-mindedness and willingness to be wrong are key to innovation and success but one must also be willing to defend their points humbly and intelligently to convince when required; a delicate balance once again.

Never Tell a Crazy Person They Are Crazy

I think this was my favorite lesson. In short, recognize that people will have their breakdown moments and may act irrationally for all sorts of reasons. When this happens, let people have their dignity; give them a way back in to the project while saving face. This may save what could otherwise be the loss of a key team member. Tina gave a great example of this. She literally ran away from the SNL studios during a very high-tension situation. The outcome could have been very negative for her and Lorne was clearly aware she had bolted. However, to rectify the situation, he simply called her up and said: “Hey, we’re ordering diner, what do you want?” to get her to come back.

There is so much going on in this simple sentence. First, Tina is absolved of the perceived irreversible nature of her actions by being given a chance to correct the situation with no questions asked. Lorne basically says the following with that sentence: “Listen, I know you freaked out a few minutes ago. It doesn’t matter. I won’t hold it against you. Come back and let’s pretend like it never happened”. The power of subtext…

This quirky exchange also drove this point home for me:

“My neighbor is crazy. He thinks he is a chicken.”
“Well, have you told him that he isn’t one?”
“No, I’m not planning to because I need the eggs.”

What I Liked About Bossypants

• Tina Fey wrote as she speaks. Unfiltered, honest and pulling no punches. This gave a great flow to the book which was a big part of its enjoyability. There were so many great, reusable quotes and a whole lot of practical examples to illustrate her points.
• Poignant examples of the challenges that working moms face while trying to juggle a career and a family. However, I thought a lot of these could apply to any working parent regardless of gender.

What Could Have Been Better in Bossypants

• The writing style sometimes seemed rushed. Tina’s writing process often left wanting more details and context. I guess this is normal for a 5 hour read book but I was disappointed nonetheless.
• In relation to the above, I found there were big parts of Tina’s life which were skipped over which left gaps in the narrative. Of course, I don’t think she meant the book to be an exhaustive biography, but it lacked structure and clarity in my opinion. This is absolutely because I’m always reading non-fiction books…

Rating: 3/5

This was a quick, fun read that I would recommend as entertainment or to satisfy your curiosity if you are a big Tina Fey, Second City and/or SNL fan. It got me laughing out loud a few times. However, the author’s self-deprecating writing style takes its toll on the flow in the later stages of the book. It makes the structure feel half-baked and that the content lacks depth. Both these elements had me asking myself: “Ok, what is happening now?” and that’s a question the reader should never have to ask himself.

Personal Library Worthy?  No. Although it was an entertaining read, I don’t see myself referencing this book in the future. Wondering what should be in your library? See my recommendations here.

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What did you think of Tina Fey’s book? How does it compare to other autobiographies you’ve read? Are you a 30 Rock viewer?

Last Updated on December 22, 2020 by Joël Collin-Demers