When You Want To Be #Boss (And Beyond) Reach For These 10 Books

Sarah Hill

Former media junkie, turned startup co-founder & CEO of @Bookstr. Focused on books, business, tech, & women in the workplace.

As a millennial woman who just took on her first CEO role, I know what it’s like to dream big. It took a lot of mental energy to shift my five-year plan from "someday" to "today," and replace the voices in my head saying, “It’s not your turn,” with a "Powerful Woman" soundtrack. It can be just as tough to balance the networking events that will help to navigate the career jungle gym (no more ladders, ladies!) with quiet nights at home practicing pitches and putting the finishing touches on reports.

But the thing I wish someone had told me sooner is that you can learn a lot about being a leader today from reading books. Not just historical biographies of the mostly white dudes who made it (although those help too – I’m looking at you, Alexander Hamilton), but also books about the importance of financial security and why we should be saying yes when we are so exhausted that every ounce of us wants to say "no."

The way to the top is paved with books.

Whether it’s a book about feminism and building bonds with the women who will give us a leg up in our careers, or a book about our sisters of all races and how our history hasn’t always been pretty, I’ve laid out my top picks for the books to read to take your next step forward.

After all, isn’t that what books are for?

1. Alexander Hamilton by Ron Chernow


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If you haven’t read this yet get on it. It’s not just that award-winning play by Lin-Manuel Miranda — he was inspired by the riveting biography by Chernow. But it’s also a story about a young man who started out life as an orphan and came to New York City to launch his career, only to be told by his role model to “Talk less; smile more.” Sound familiar, ladies? Instead of backing down, Hamilton stands up for what he believes in and, well, the rest is history.

2. The Song of Achilles by Madeline Miller

This book is listed as Young Adult, but don’t let it fool you. This is a beautiful novel based on the retelling of The Iliad, and it is perfect for this moment as we are looking back to the past for insight into our futures. It’s about love, war and everything in between — and it teaches us that not only does history repeat itself, but also that one person can, and does, make a difference.

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(Photo by Melissa Pitz, courtesy of Jessica Bennett)

3. Feminist Fight Club by Jessica Bennett

It’s a manual! It’s a manifesto! It’s the battle cry we all need — no matter what we’re fighting for. From those micro-aggressions around the water cooler to tips on fighting today’s sexism, this book offers a blend of personal story and practical push-backs for working women everywhere.

4. How to Be a Financial Grownup: Proven Advice from High Achievers on How to Live Your Dreams and Have Financial Freedom by Bobbi Rebell

Read this and get your finances in order. Whether you’re a math whiz or terrified of all things financial, this book is informative without being patronizing. More importantly, it’s actionable. Whether you make $30,000 or $300,000 you will finish the book understanding how to take your real life goals and make them a reality.

(Photo courtesy of Randi Zuckerberg)

5. Dot Complicated: Untangling Our Wired Lives by Randi Zuckerberg

Who better to offer advice and insight on how technology influences our lives online and off than Zuckerberg, who was on the frontlines of Facebook as a marketing executive for six years? Part memoir, part manual, Zuckerberg helps us navigate our new online reality at a time when the Internet can break our careers – and our country – with the push of a button.

6. Today Will Be Different by Maria Semple

From the author of Where’d You Go, Bernadette? comes a charming novel that puts the pettiness and problems of being a modern woman into humorous and stark relief. The main character, Eleanor Flood, is Everywoman: She promises herself she’ll tackle her to-do list and stick to her resolution to go to yoga. But as it turns out, life doesn’t always go as planned, and those wrenches make for a hilarious page-turner.

7. Hillbilly Elegy by J.D. Vance

As go-getters, we need to understand the world around us — not just the bubbles of our offices and friend circles — but stories of those we may not have known were living in our own backyards. Vance’s memoir gives us a searing look into one man’s family and what they tell us about the working class in America.

8. Stamped from the Beginning: The Definitive History of Racist Ideas in America by Ibram X. Kendi

Winner of the 2016 National Book Award for nonfiction, this book takes a deep dive into racism in America. Given our political moment and the work we need to do as individuals and as a country, this book should be on every young leader's bookshelf. It’s not pretty, but the truth often isn’t.

9. The Sellout by Paul Beatty

Winner of the Man Booker Prize, this laugh-out-loud read satirizes the often painful truth about race, pop culture and politics in America. As leaders looking to take our next step forward, this book helps us understand what’s standing in our way.

(Photo courtesy of VALERY HACHE/AFP/Getty Images)

10. The Year of Yes by Shonda Rhimes

This book by Rhimes, the creator of "Grey’s Anatomy," "Scandal" and other hit shows is, like its title suggests, about saying "yes." But it is also a memoir about what it means to be an introvert who unconsciously sabotages herself because she’s afraid. Rhimes spends years leaning out, relying on the fact that she’s “too busy” (and we all know she was), until her sister gives her a wake up call. That’s when Rhimes forces herself to own her platform and to say "yes" to loving her true self.

What is a book you read this year that you would recommend? Tell us!

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