WLT Book Club Highlights: Bossypants by Tina Fey

Tina Fey, creator and star of 30 Rock and the first female head writer at SNL, was one of the keynote speakers at the recent Pennsylvania Conference for Women, which our team had the honor of attending this year. We were beyond excited to hear Fey share insights from her life and career, and she certainly had a lot to teach from her experiences. Most notably, she emphasized the importance of humor as a tool for connection, encouraged women to regularly advocate for themselves, and reflected on cultivating a happy and collaborative team behind the scenes at 30 Rock.

This amazing experience lined up perfectly, as the Women’s Leadership Today Book Club had just finished reading Fey’s bestselling memoir, “Bossypants.” For professional women navigating their careers, Bossypants offers an enjoyable and illuminating read. Fey’s memoir brims with witty, self-deprecating humor while also imparting wisdom accrued from her experiences in male-dominated writers’ rooms. Though Fey made her name in comedy, her insights resonate across industries and career stages.

One theme that leaps off the page is Fey’s belief in the power of humor. She argues that joking humanizes leaders, forges connections, and provides an essential pressure valve. Reflecting on her time as head writer at SNL, she explains “You have to create an environment where people feel safe enough to talk about ideas that might sound crazy at first.” At 30 Rock, humor set a fun, relaxed tone that encouraged the staff to take risks and do their best work. Fey reflected on this at the conference as well. She talked about how she aimed to create an environment where people enjoyed working hard together. To do this, Fey focused on empathy, communicating clearly, and accommodating her team’s needs when possible. She also made it a point that she prioritized maintaining her own happiness outside work. Fey believes humor and heart created the conditions for 30 Rock to succeed for seven seasons.

Another key theme is the importance of women advocating for themselves, especially around compensation. Fey emphasizes that no one will simply hand you what you deserve; you must ask for it – often repeatedly. She shares how she leveraged other offers to negotiate her salary for 30 Rock, even though it meant bluffing a bit. Fey sees self-advocacy as an obligation successful women have to the generation coming up behind them.

While some advice draws directly from Fey’s comedy career, the book still brims with relevant takeaways for leadership, culture, and work-life integration. Our book club found Bossypants highly motivating and laughed together and often at Fey’s jokes. I’d recommend it to all professional women seeking an entertaining yet empowering read. Tina Fey’s unique path makes her reflections feel hard-won yet accessible. Bossypants is the rare career memoir that delivers plenty of laughs along with leadership lessons, providing a funny, honest guide for making your way and lifting up others in the corporate world.