When I was in kindergarten, I peed my pants in the middle of an in-class exercise. It was a follow-the-directions-carefully assignment, and I was terrified that I would be kicked out of school if I asked to go to the bathroom. My bladder was about to explode, but my teacher had told us that it was crucial to pay attention to every single thing she said. I was confused, uncomfortable, terrified, and helpless. But I thought I wasn’t allowed to move. So I just went for it. I let that apple-juice-inspired explosion get the best of me.

That’s kind of what it’s like to be in your twenties. You’re told one thing but you’re expected to do another. No one cares how uncomfortable you are. You don’t know whether to listen to yourself or to the 50 different people shouting in your ear about “what’s best for you.” You often feel powerless. So you metaphorically pee your pants and stare defiantly at your classmates while they watch pee run down your leg. 

Unfortunately there’s no solution for getting through your twenties unscathed. But there is a way to ease the pain a little bit: books. Here are 17 that will help you get through even the messiest quarter-life crisis. 

1. The Defining Decade by Meg Jay

The Defining Decade essentially tells you how to get your shit together while you’re in your twenties and you still have time. While it’s true that our twenties are meant for exploring, experimenting, and trying new things, Jay also explains why it’s crucial to start planning for the rest of our lives right now. By dividing the book up into three sections (Work, Love, and The Brain and the Body) she provides an excellent road map for any twenty-something to refer to while we are trying to figure ourselves out.

2. Daring Greatly by Brené Brown

This book shows you that it’s not only okay to be vulnerable, it’s absolutely necessary. In a world where we live under the fear of constant criticism, it’s amazing to read a book that shows you how each hardship you go through makes you into a stronger person. Twenty-something’s in particular feel a strong pressure to put on the facade of a perfect life to those around them. This book tells you to do the opposite of that. You’ll savor every page. 

3. The Genius In All of Us by David Shenk

Before I read this book, I subconsciously categorized people into two groups: those born with talent, and those who aren’t so lucky. But this book destroys anything you ever thought about innate talents, gifts, and abilities. It explores the brain and human development, and how talent actually comes about: through hours and hours and hours of dedication. Whatever your goal is in life, this book makes you believe you can get there, as long as you’re willing to throw every ounce of sweat, blood, and tears you have into it. 

4. The Harm in Asking by Sara Barron

Maybe I’m just a sucker for self-depricating humor, but this book will make you feel good about yourself no matter how much of a shitshow your life is at the moment. In a series of hilarious essays, Barron catalogues what it’s like to be a directionless human being trying to make their way through a judgmental world. This book is both a great comfort and an easy way to make you smile if you’re feeling unenthusiastic about where you are in life. 

5. Why We Suck by Denis Leary 

If you’re looking for something smart, irreverent, and hilarious that will take your mind off work and make you laugh for a little bit, this book is it. Comedian Denis Leary takes on everything from racism to Dr. Phil, and he has an incredible way of finding the humor in even the most dire of circumstances. On the days where you feel like you hate the world and you need someone to commiserate with, open this book and you’ll be cackling in no time. 

6. Girls in White Dresses by Jennifer Close

This book was an unexpected gem for me. Last March I was stuck in the Minneapolis airport with a four-hour layover. I was sick and cranky and I didn’t feel like reading something that was going to make me think. So I picked up this little number and thought “Ehh… let’s give it a shot.” It ended up being an extremely well-written, funny, and honest book about the pressures placed on young women to have it all (a career, a husband, and a perfect life) before the age of 30. The characters are real women with real issues, and you feel like you’re reading stories about some of your best friends. I seriously suggest this book if you need a simple reminder that you’re not alone in what you’re going through. 

7. Bossypants by Tina Fey

This is probably on every single list of books to read in every single category you can imagine, and I DON’T CARE because it’s amazing and everyone needs to read it. Bossypants is a light, easy read, but it still makes you think. Tina Fey talks about what her life was like before she was a mega-successful badass, and it’s encouraging to remember that everyone, even the Tina Fey’s of the world, has to start somewhere. 

8. How Did You Get This Number by Sloane Crosley

Sloane Crosley just knows how to write. This collection of essays takes you all over the world, including a trip to Portugal that Crosley decided on merely by spinning a globe and sticking her finger on it haphazardly. Although the situations and experiences she finds herself in are extremely strange and absurd, it’s still relatable because she’s just as lost and uncertain about her life as most of us are. These essays take the overwhelming, everyday emotions most of us experience in our twenties and turn them into funny and truthful observations about life.

9. Rebounders by Rick Newman

Fear of failure is all around us. Thanks to social media, we’re conditioned to think that we have to constantly be announcing job promotions, beautiful apartments, big raises, gorgeous new wardrobes, and everything in between. If we fail at something, there’s a feverish hurry to sweep it under the rug and keep it quiet. This book is for everyone who has ever struggled with that fear of failure. It explores the backgrounds of some of the most successful people in the world, including the founder of Netflix, the CEO of Dunkin’ Donuts, and the creator of Pandora, and how they encountered failure after failure before they finally got somewhere. Rebounders shows you that it’s okay to fail, and that it’s the failures you experience that are truly going to mold you into the successful person you hope to one day become. If you’re scared of failure and success and everything in between, this book will be your saving grace. 

10. The Perks of Being a Wallflower by Stephen Chbosky

When you get into your twenties, it’s easy to forget how awkward and difficult, and yet simultaneously enlightening and exciting, that high school could be. But I think it’s important to remember what that time period was like, because it reminds you of how far you’ve come. Your twenties are definitely challenging and overwhelming, but you forget how much you’ve grown until you look back at yourself in high school. Perks is a wonderful way to take yourself back to that time – those moments in high school when you felt like you couldn’t get out of bed, as well as the moments where you felt like nothing bad could ever happen to you. Plus, if you read this book, you’ll finally know what people are talking about when they use the quote “And in that moment, I swear we were infinite.” 

11. Is Everyone Hanging Out With Me? by Mindy Kaling

Kaling’s hilarious memoir is filled with incredible advice and observations that millennials will actually find useful, such as “If I’m at a party where I’m not enjoying myself, I will put some cookies in my jacket pocket and leave without saying good-bye.” Reading her book feels like you’re just sitting with a friend at a bar and listening to them talk about awkward situations you’ve found yourself in all too frequently. Kaling also has the gift of being extremely open and vulnerable about her struggles and insecurities, which will leave you feeling connected to her on a deeper level.

12. The Tipping Point by Malcolm Gladwell

The “tipping point” is the moment when a product, idea, fad, person, or movement goes from being average to a being sensation. Gladwell explores various tipping points in his book and researches exactly what happens when something becomes a worldwide phenomenon. It’s an amazing read for a twenty-something because it reminds you of the incredible potential you have. You don’t have to do something crazy to bring about change. In fact, The Tipping Point shows you that it’s the opposite of that: the tiny, little ideas are the ones that have the possibility to change the world.

13. Seriously, I’m Kidding by Ellen DeGeneres

Ellen’s been through a lot in her life. She’s dealt with rejection, bigotry, failure, loneliness, and everything in between. I’m sure she still encounters it everyday, but she’s managed to become one of the most successful entertainers in the world today. So if you’re going to take life advice from anyone, I suggest you start with her. This book contains plenty of lighthearted moments, but she also shares a great deal of insight that will leave you feeling encouraged and uplifted.

14. The Casual Vacancy by J.K. Rowling

With J.K. Rowling’s name on the cover, I shouldn’t have to give you a reason to read this book, but I will anyway. Rowling writes about life in a small English town from the perspective of multiple characters of all different ethnicities, genders, ages, and socioeconomic statuses. What is so brilliant about this book is that she captures everyone’s internal struggles perfectly, no matter what that struggle is. When you’re a twenty-something, you feel like everyone else around you (especially those much older than you) has their life together and you don’t. This book takes you into the perspectives of those types of people and shows you that although you wouldn’t know it, everyone is struggling with something. You’re not alone.

15. Chelsea Chelsea Bang Bang by Chelsea Handler 

I can’t not have a Chelsea Handler book on here. If you’re feeling down or unmotivated and you just need to hear from a badass chick who’s running the show, Chelsea Handler is your answer. I’m a fan of every one of her books, but I chose this one in particular because I once read it while I stood in a customer service line for a canceled United Airlines flight for three hours. Everyone around me was pissed off and on the brink of punching each other, but I stood there completely carefree and laughing like an idiot because of this book. The writing is quick and smart, and it will keep a smile on your face, even if you find out you’re stuck overnight in the airport because United is the worst.

16. The War of Art by Steven Pressfield

As Pressfield explains, Resistance is all around us. The Resistance he’s referring to is that which keeps us from doing what we truly want to do – whether it’s writing a novel, forming a start-up business, or creating the next life-changing app. Pressfield teaches you how to overcome your biggest critic: yourself. This is the book that will force you to stop making excuses and start tapping into that creative part of you that you’ve always been afraid to acknowledge and develop. 

17. Bird by Bird by Anne Lamott

Although Bird by Bird is primarily a book about writing, it’s an inspiring and memorable read for writers and non-writers alike. The book is almost childlike in its innocence, but Lamott also writes with the kind of wisdom that comes from years of rejection, perseverance, and tenacity. The prose is simple and relaxing, but it still challenges you to open up your eyes and witness the world around you. And in your twenties, that’s some damn good advice to receive. TC mark 









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