12 Books Every Ambitious Woman Should Read

A few days ago I was reading author Elizabeth Gilbert’s Facebook page — because a day is just not a day until I’ve gotten my dose of Lizzy G. — when I read the words: “Are there perhaps better virtues to cultivate than mere ambition?” Hmm, I thought. And then there was overwhelming relief, followed almost immediately by overwhelming panic.

"Ambition" can be a tricky little word. Eight unassuming letters that when lined up together have the ability to strike equal parts excitement and terror in the hearts of people everywhere (and if you’re anything like me, mostly just terror.) For me, the word ambition is usually accompanied by an onslaught of questions: Am I ambitious enough; driven enough; talented enough? Should I be working more? Should I be working less? Do I have the right pants for ambition? Should I spend more time in New York, Los Angeles, Washington D.C., Paris? Should I move to Brooklyn and pay $1200 a month to live in someone’s closet while I finish my novel? Should I move to rural Tibet and pay 6,000 yuan a month to live in a yurt while I finish my novel? Should I drink more wine, drink more espresso, do more yoga, hang out with more artists, hang out with fewer artists, take a vow of silence? Do I actually have any ambition at all?

Phew. Ambition can be a little exhausting.

But in the right dose ambition can also be totally, wonderfully motivating — just ask the writers of these books about ambition. Whether you’re an artist or an activist, a totally badass girlboss or a brainiac lady of the sciences, or something else entirely, these books will inspire you to follow your ambition (while reminding you that you’re already amazing, so give yourself some credit on the way up.) Here are 12 books every ambitious woman should read, because sometimes we all just need a little reminder that we’ve totally got this.

Big Magic by Elizabeth Gilbert

Elizabeth Gilbert's Big Magic is definitely not just a title for ambitious ladies in the arts. The writer herself defines creative living as: "living a life that is driven more strongly by curiosity than by fear." Who isn't totally on board with that? Filled with great advice and personal anecdotes, Big Magic acts like a step-by-step guide for anyone interested in following their ambition a little more closely, or reigniting it all together.  

#GIRLBOSS by Sophia Amoruso

Founder, CEO, and creative director of online fashion retailer Nasty Gal, Sophia Amoruso's climb to the top was anything but typical. From a hitchhiking, petty thief to becoming her own boss, she tells you the whole story in candid, no-nonsense prose, in her part-memoir, part-guide to success, #GIRLBOSS

Outliers by Malcolm Gladwell

In Outliers journalist Malcolm Gladwell takes a scientific look at the myriad factors that contribute to high levels of success. From Canadian ice hockey players to The Beatles, Gladwell explores the different paths to and definitions of success, and advocates for something he calls the "10,000 hour rule," which is basically a friendly reminder that practice makes better. 

The Woman Upstairs by Claire Messud

A novel filled with the unavoidable complications of having too-much or too-little ambition, The Woman Upstairs tells the story of Nora, an artist-turned-elementary-school-teacher who somehow became everything she thought she'd never be, and an ambition-filled family who changes her life forever. This may not be a how-to for changing your own ambitious life, but it'll definitely entertain and make you think differently about what some people will do to follow their ambition, and what others allow themselves to let go of.

The Icarus Deception by Seth Godin

Everyone knows the Greek myth of Icarus — a boy who took flight via wings of feathers and wax, and who defied his father's instructions by flying too close to the sun, where his wings melted and sent him plummeting back to earth — essentially a cautionary tale of too much ambition. The Icarus Deception turns that tale on its ear, instead advocating for flying high, reaching far, and aspiring to greatness. After all, as the famous poet Jack Gilbert wrote: "Everyone forgets that Icarus also flew."

If You Have to Cry, Go Outside by Kelly Cutrone

Tough words from fashion and PR maven Kelly Cutrone; but also super good advice (this is coming from someone who has definitely cried in the office before and regretted it. Now I'm a writer who works from her living room, so I can cry whenever the hell I feel like it.) If You Have To Cry, Go Outside features Cutrone's honest, no-holds-barred career advice, and combines stories from both her personal and professional life, illuminating what it means to be a success without sacrificing who you are in the process. 

Still Lifting, Still Climbing edited by Kimberly Springer

This gorgeous collection of academic and personal essay tells the story of black women's activism in America after the Civil Rights Movement. Still Lifting, Still Climbing features inspirational and empowering stories of success in areas of feminism, anti-rape campaigns, mass incarceration reform, welfare rights, women's healthcare, and labor organizing. This is a must-read collection for any politically motivated, world changing activist. 

The Best of Everything by Rona Jaffe

Rona Jaffe's novel, The Best of Everything, explores the idea that women really can have it all — ambition and success, love and family, professional lives as rich and complex as their personal ones — and more. Following the fictional stories of five women living and loving in New York City this novel, which was first published in 1958, still speaks to the experience of ambitious women everywhere today. 

Bossypants by Tina Fey

If you've ever wondered how the hilarious Tina Fey ended up where she is today, look no further than Bossypants. Fey recounts everything from her humble upbringing to her career highs and lows, and the unique experience of being a hugely successful woman in comedy. Bossypants takes the much-touted idea of becoming an "overnight success" and shows the kind of hard work that having great ambition actually requires. 

I Know Why The Caged Bird Sings by Maya Angelou

The poetic autobiography of author Maya Angelou, I Know Why The Caged Bird Sings tells the story of how one woman's creative ambition allowed her to overcome a series of born-into setbacks (racism, the political climate of America, physical and emotional trauma, being a woman in a male-dominated culture) and become one of the most celebrated writers of all time. 

Quiet by Susan Cain

For all the introverts out there (me) this one's for you. In Quiet, Susan Cain disputes the idea that introverts must overcome their inclination to silence in order to become successful and recognized members of society. Using examples of hugely transformative introverts — Rosa Parks, Chopin, and Steve Wozniak, to name a few — she shows how essential the introvert is to society, and how the natural skills of an introvert (listening, hesitancy to self-promote, independence) are some of the exact qualities needed to follow one's deepest ambitions. 

Hope for the Flowers by Trina Paulus

A children's book written for adults, Hope for the Flowers tells the story of two caterpillars and their individual races to the top. While they both get there, one caterpillar realizes life at the top might not be everything he'd hoped for. This book is a great, quick read for anyone who might be questioning their ambition, or seeking a greater balance between a fast-paced professional life and a deeper personal one. 

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