20 books to read in your 20s header image

Some say their twenties were the best years of their lives. Others couldn’t disagree more. Regardless of the type of experience you have, our twenties are certainly a time of change, transition, and challenges.

It’s a decade full of questions and quests as we try to figure out who we want to be and search for the person who is supposed to “complete” us. 

More often than not, though, the decade concludes with just as many questions (if not more) than we had to begin with. 

We might find love only to lose it. We might lose a parent or have to face the end of lifelong friendships. We might find what we thought was our dream job, only to realize it wasn’t really what we wanted at all.

It’s a confusing time, to say the least. But the good news is, we’re all going through more or less the same struggles. 

Books Every 20-Something Must Read

The following 20 books provide wisdom, inspiration, and sometimes a little comic relief to help you get through this turbulent decade.

But more importantly, they serve as the perfect reminder that we’re not alone as we learn to face loss, love, and other life lessons.

1. The Defining Decade by Meg Jay

To anyone who says that your 20s don’t really matter: Dr. Meg Jay begs to differ. In The Defining Decade, the clinical psychologist uses science and real-life stories to argue that our personalities, relationships, and identities can change more in this decade than any other time in our lives.

Dr. Jay provides a smart and practical guide to making the most of these transformative years.




2. The Alchemist by Paulo Coelho

The Alchemist is a modern classic that deserves a read no matter what your age is.

Through the mystical story of Santiago and his adventurous travels, Coelho offers readers important lessons about listening to their hearts, following their dreams, and recognizing opportunity—making this a perfect read for young adults still feeling insecure about their life’s path.

3. The Good Girl’s Guide to Getting Lost by Rachel Friedman

For anyone who’s feeling pressured into the prescribed post-college formula (finding a safe job, getting married, raising children, retiring comfortably), Rachel Friedman offers up her own story to prove that there are alternative routes to a fulfilling life.

The consummate good girl shocked everyone when, following graduation, she bought a one-way ticket to Ireland. What followed was a year-long odyssey that brought her to three continents and filled her life with love and new friendships. What started as a quarter-life crisis led Rachel to realize the importance of living her life for herself. 

4. Becoming by Michelle Obama

It’s hard to believe, but even Michelle Obama struggled to find her calling. In this memoir, the former First Lady recalls all of the hard work it took to defy society’s expectations of a girl growing up on the South Side of Chicago.

She also describes the self-reflection that forced her to admit (post-Harvard) that being a corporate attorney wasn’t her passion. As she describes her triumphs and disappointments, Michelle reminds all of us that it’s okay (and never too late) to change direction.

5. The Opposite of Loneliness by Marina Keegan

Marina Keegan graduated magna cum laude from Yale in June 2012. She had a job waiting for her at The New Yorker and had written a play that was to be produced at the New York Fringe Festival. Then, tragically, Keegan was killed in a car accident just five days after her graduation.

The Opposite of Loneliness is a collection of deeply rich essays and stories that Keegan left behind. A voice for her generation, Keegan brilliantly captures the universal struggles that all of us face as we try to figure out who we want to be as we face hope, uncertainty, and endless possibility.

6. The Myths of Happiness by Sonja Lyubomirsky

Sonja Lyubomirsky debunks the myths we’ve all been told: that once we hit those markers of adult “success,” we’ll finally attain happiness. She explains how this “black-and-white vision” of happiness limits our growth potential and discourages us from finding an upside to any negative situation.

The Myths of Happiness is here to remind us that we are more adaptable than we think—and that it is usually our mindsets, not our circumstances, that matter most. 

7. A Single Man by Christopher Isherwood

Christopher Isherwood captures a single day in the life of a middle-aged gay man adjusting to solitude following the sudden death of his partner. Even through his episodes of grief, rage, and loneliness, George is determined to carry on with his everyday life—because despite the injustices he faces each day, he still loves being alive.

A Single Man was developed into a highly-acclaimed feature film in 2009, starring Colin Firth. It’s the perfect reminder that no matter how hard life gets, there’s always a reason to carry on.

8. One Hundred Years of Solitude by Gabriel García Márquez

Gabriel García Márquez uses magical realism to capture seven generations of one family and their settlement in Colombia.

Through wars and disasters, wonders and miracles, One Hundred Years of Solitude provides a profound look at the nature of time, solitude, and an ever-present past to remind us that time extends well past our twenties (even if that’s sometimes hard to believe).

9. Design Your Future by Dominick Quartuccio

Sometimes it’s easy to feel like life is happening to us, especially during our twenties. Mentor and author Dominick Quartuccio shows us how to break through our “self-imposed ceilings” and start consciously designing our own futures.

Quartuccio challenges readers to reclaim control of their lives by realizing their hidden beliefs and disrupting their self-destructive patterns—definitely helpful advice for twenty-somethings who feel they’ve lost control of their futures.

10. Very Good Lives by J.K. Rowling

In Very Good Lives, J.K. Rowling trades wizardry for words of wisdom as she recalls her own post-graduate experiences and addresses some of life’s most important challenges.

An extended version of Rowling’s 2008 commencement speech at Harvard University, this book is perfect for anyone facing a turning point in life. Rowling teaches readers why they should embrace failure and use their imaginations to better themselves and others.

11. Yes Please by Amy Poehler

With the hilarious wit that only Amy Poehler could deliver, Yes Please offers a collection of stories and advice that will inspire readers as much as it makes them laugh. 

With chapters such as “Treat Your Career Like a Bad Boyfriend,” Yes Please delivers life lessons and big laughs thanks to Poehler’s talent and wisdom, drawn from years of her own experiences.

12. Transitions by William Bridges

Whether we choose them or not, our 20s are definitely filled with transitions—some easier than others. In this bestseller, William Bridges offers advice on navigating some of life’s biggest changes by taking readers through the three stages of any transition: The Ending, The Neutral Zone, and The New Beginning.

Whether you’re facing personal or professional transitions, this book is here to guide you through life’s one constant: change.

13. The Secret History by Donna Tartt

The Secret History tells the story of six eccentric classics students who begin to experiment with the bounds of normal morality and eventually turn on one of their own by pushing him to his death.

Ultimately, The Secret History shows us what happens when boundaries are eroded and life as we know it no longer exists.

14. The Doctor Is In by Ruth Westheimer

Though you might know her as the famous and trusted sex therapist, Dr. Ruth has endured more than her share of hardships, from surviving the Holocaust to working as a sniper during Israel’s War of Independence.

Through intimate and often hilarious stories, Dr. Ruth shows us how even in the face of tragedy and loss, she’s learned to live a life of joy. Her inspiring tales will have readers reconsidering how they think about life and love.

15. Modern Loss by Rebecca Soffer and Gabrielle Birkner

For many of us, our 20s mark our first real experiences of loss and grief. Whether it’s the loss of a parent, a relative, a friend or colleague, navigating grief can be incredibly challenging.

Modern Loss offers advice on coping with grief, especially in this desensitized age of social media. Both brutally honest and inspiring, Soffer and Birkner invite readers to talk openly about loss and confront the mortality we all share.

16. Fates and Furies by Lauren Groff

Named by Barack Obama as his favorite book of 2015, Fates and Furies focuses on the tumultuous years of one couple’s marriage—primarily through their 20s and 30s—as they finish school, begin new careers, and enter early middle age.

Groff illustrates how two people can have tragically different views of the same relationship, while at the same time making a partner’s “unknowability” seem almost bearable. 

17. How to Lose Friends and Alienate People by Toby Young

In this memoir, Toby Young documents his failed efforts to conquer New York and make it big as an editor for Vanity Fair. The British journalist had it all within his grasp—working his dream job, rubbing elbows with celebrities, and climbing steadily up the social ladder. But within two years, he managed to lose it all.

Through hilarious self-deprecating anecdotes, How to Lose Friends and Alienate People serves as the perfect cautionary tale of how quickly our luck can change while holding a mirror to our own celebrity-obsessed culture. 

18. Algorithms to Live By by Brian Christian

Wouldn’t life be so much easier if there were a code for happiness? Brian Christian and Tom Griffiths think they’ve found a solution. In Algorithms to Live By, the two authors demonstrate how algorithms developed for computers can also untangle human questions.

Learn how computer science can be translated into strategies for everything, from dealing with overwhelming choices to finding a spouse.

19. Tiny Beautiful Things by Cheryl Strayed

Cheryl Strayed was once the anonymous voice behind an advice column for The Rumpus. She’s now sharing the best of her columns (as well as new pieces) to offer honest and often hilarious advice for dealing with life’s harder moments.

Thanks to her compassionate narratives, Strayed’s words of wisdom will surely resonate with anyone who has lived through life-changing experiences.

20. One Hour Investor by Vishal Reddy

You’ve probably heard that it’s never too early to start saving. But with all the other things to worry about in your 20s, who has time to figure out investing? Vishal Reddy will walk you through all the basics in just one hour.

One Hour Investor shows beginners how to invest wisely in stocks, mutual funds, and bonds without the need for a foreign language interpreter. Start learning to save even in your 20s so you can feel ready when retirement comes around. 

Learn Through Reading

No matter what is going on in your life, books can be a great source of wisdom and comfort. Reading a variety of fiction and nonfiction will not only help you through your 20s, it will also expand your mind and broaden your horizons.

To find more great stories for every age, check out some of TCK’s newest book releases.

What’s one book that inspired you during your 20s? Feel free to share in the comments below!

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