1. I Know Why the Caged Bird Sings by Maya Angelou
Eventually, every teen will have to come to terms with suffering and loneliness. This book is a testament to how to approach even the deepest trials of life. Angelou’s memoir of her childhood is heart-breaking and tragic, but the strength of her spirit, her unabated optimism and hope, and the incredible poetry of her words help readers make sense of life, even at times when that seems impossible. Maya shows us that it’s possible to nurture something inside that can glow brightly, even in the darkest night.
2. The War of Art by Steven Pressfield
This book highlights a very uncomfortable truth about life: if you want to create something, you will face many, many roadblocks. Whether it’s naysayers, self-doubt, or laziness, there are loads of things that will keep us from doing what we long to do. Pressfield helps us easily and clearly identify the enemy of creativity, and like Sun Tzu, outlines a battle plan to conquer this internal foe. Think of it as tough love . . . for yourself. Whether or not your teen is traditionally dubbed “creative” this book will help them see that nothing good happens unless you master the toughest foe out there: yourself.
3. Do Hard Things by Alex and Brett Harris
The fact that the foreword to this book is written by Chuck Norris is only the second coolest thing about this book. Alex and Brett Harris, who themselves are teenagers, do a firm job of making the case that low expectations hurt teens, and that high expectations push people to do more. The Harris boys explode the myth of adolescence and show that prior to the 20th century, a person was either an adult or a child. And they make a strong case that teenagers are capable of a whole lot more than society thinks. This book is challenging to teens. And adults, frankly.
4. Boundaries by Dr. Henry Cloud and Dr. John Townsend
One of the most important realities of life is that every person has limits and limitations. This book makes the case that if a person doesn’t set and establish and hold strong boundaries for themselves, then bad things will happen. Your teen must have physical boundaries (the wisdom to determine who may touch us and under what circumstances), mental boundaries (the freedom to express our own thoughts and opinions) and emotional boundaries (the ability to manage our own feelings and disengage from the manipulative emotions of others). There are adults who can’t do this. To have Cloud and Townsend help your teen understand and internalize these truths is beyond helpful.
5. Don’t Know Much About History by Kenneth C. Davis
History is important. But taught wrong, history can be an absolute snooze-fest. But not here. With trademark humor and a super-engaging conversational style, Davis is the most interesting history teacher you’ve ever had. He explains important events and people in ways that make sense even of the most complicated moments in US History. And after all, making sense of the past and learning from it might be the best way to prepare teens for the future.
6. To Kill a Mockingbird by Harper Lee
This is very nearly the perfect book for teenagers, and a classic American novel. The novel’s themes of racial and social injustice are tough to watch unfold, but the story is told with such goodness (and warmth and humor) that it’s nearly universally loved. In fact, we don’t trust anyone who doesn’t love this book. And TKAMB is so powerfully written, that it can actually accomplish something incredible in its readers: it can build empathy for the “other.” And if there’s one thing teens need in today’s world, it’s more empathy.
7. How to Win Friends and Influence People by Dale Carnegie
In the new knowledge economy, one of the most important traits that employers are looking for is the ability to co-exist and work well in collaborative settings. This book, originally published in 1936, might seem dated, but its principles are increasingly important in our era. The book might seem a tad Machiavellian in its goal, but underneath it all are strong interpersonal communication techniques based on the idea that other people are far more frail and far more egocentric that we’d all like to admit. This book really can help your teen grow into a person who is winsome, kind, respectful and saavy with other people.
8. The Total Money Makeover by Dave Ramsey
The average teen will spend nearly 3,772 hours in high school, during which time, most will spend exactly zero minutes learning about personal debt, credit card interest, compounded interest, mortgages, stocks and bonds, budgeting and other crucial concepts of personal finance which will affect them nearly every day of their adult life. This seems almost criminal. Ramsey’s book on personal finances are one of the clearest and easy-to-understand guides to money and personal finances out there. Because how you handle your money matters.
9. The Catcher in the Rye by JD Salinger
Holden Caulfield is the literature’s first unreliable narrator, a desperately lonely young man broken to the core by the tragic, traumatic death of his beloved younger brother. His struggle – the angst that comes about from trying to figure out how to belong, be known and be loved – is the story of every adolescent.
10. The Giving Tree by Shel Silverstein
Sure, it’s a children’s book. Sure, it’s the only book on here that’s illustrated. And sure, if we were going to include a children’s book, then Where the Wild Things Are is definitely more influential. But what’s fascinating about this simple book is how divisive it is. Some people loathe this book. Others, cry just opening it. Regardless, you won’t find a truer representation of the juxtaposition of humanity’s endless capacity to take and be selfish, as well as our capacity to sacrificially love, literally without condition. We are both the boy, and the tree. But maybe more like the tree than we’d like. And that’s why the story haunts us.