05/27/2014 10:59 am ET Updated Jul 27, 2014

Happy Graduation! Ten Books That Could Change Your Graduating Senior (and Their World)

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'Tis the season for long black robes and tassels on caps flying into the air, for extended families to drive cross-country to attend ceremonies, and large, ballooned and beribboned back-yard celebrations to honor those who have survived their four years of high-school or college. 'Tis also the season for the question: What to get a young person about to set off on their next adventure? Should it be a backpack for the trips they will surely need or want to make over land and over sea? Should it be jewelry, so they will have something beside an electronic device to mind? How about a new electronic device with the heft of a laptop?

Back in the day, a wristwatch passed down from parent to child sufficed. In many countries, that, or a fountain pen, still packs a punch. But in this American milieu when so many young people already have, or can acquire -- via eBay, if not via a parent's bank account or a college's determination to coddle -- what they might need to prosper and thrive, and where conversation and letters are the rarity, perhaps the more pertinent gift would be a stack of books. Here, therefore, are a few suggestions for ten of the best books for graduating seniors. And while we are at it teaching our kids right from wrong, please buy these books from your local bookstore, failing which, you can order them online from any one of these pillars of the literary community: Powells, City Lights, Boswells, McNally Jackson, Brookline Booksmith, or my personal favorite, The Elliott Bay Book Company.

1. Tiny Beautiful Things: Advice on Love & Life from Dear Sugar (Cheryl Strayed, Vintage, 2012)

This gem of a book is culled from the Dear Sugar column written by the author of Wild, Cheryl Strayed, for The Rumpus. From the young gay man who cannot afford to move out of his bigotted parents' home, to the young woman who doesn't know how she's ever going to succeed as a writer, from the guy who walks in on his friends talking disparagingly about him, to the one who wishes for a different life than the one they chose, to the one who longs to leave his middling, home-town band and strike out on his own, there is immense wisdom in the words penned by Strayed. As the Guardian puts it, Strayed's answers to a "world full of self-obsessed, fractured, self-deprecating people who just want to do the right thing," answers that are couched in writing that is "addictively (and) breathtakingly great," run along the lines of what many an elder might want to say to the younger: "Get over yourself. Ask better questions. The fuck is your life. Answer it."

2. Hope in the Dark: The Never-Surrender Guide to Changing the World (Rebecca Solnit, Nation Books, 2005)

For a generation equally jaded by issues that ought to be relics from the past (racism, sexism, capitalism), and energized by new social movements (Occupy Wall Street and the Arab Spring), Solnit's book provides the gentle, long-term view that is the backbone of every activist. In an updated edition that roams over the political territory of America, Solnit outlines the changes that have taken place, nudging her reader away from a path on which so many like to settle: "excoriating the wall for being so large, so solid, so blank, so without hinges, knobs, keyholes, rather than seeking a door, or (trudging) through a door looking for a new wall." Read in her easy prose, this is a dazzling account of possibility that celebrates victory over overwhelming odds: the fall of the Berlin wall, the Zaptista uprising in Mexico and the anti-globalization demonstrations in Seattle on the cusp of the new century, among others. It is both a galvanizing call to action to young people who may have grown comfortable with clicking "like" on Facebook and the occasional re-tweet, and an assurance that all shall be well in the end.

3. A Small Place (Jamaica Kincaid, Farrar, Straus and Giroux, 2000)

No generation has traveled with as much as ease of access to information and passage as has this one. Most young graduates would have done more than leave their home-towns at least once, and many have been in other states and across national borders. Yet how many of them understand the global historical and political context within which these journeys take place? Kincaid's book is a reminder that nothing we undertake is without ramification. Although the slim, eighty-one page autobiographical/fictional novel is set in Antigua, it is a sharp examinatio of tourism as a neo-colonial structure that is replete with voyeurism rather than engagement. The beauty of the places we live in and visit is often at odds with the reality of inequality, injustice, and corruption that we choose to ignore. For young people who are called upon so frequently to consider international service during times of disaster, or foreign-study, Kincaid's book is essential reading.

4. The Magic Mountain (Thomas Mann, Knopf, 1927)

Considered one of the most influential work of German literature in the 20th century, Mann's novel, a classic bildungsroman -- a novel of education and formation - is a perfect pick for a young graduate. The story unfolds in the lead up to World War I and begins when the orphan Hans Castorp leaves his familiar life replete with mundanity, to make a journey to the Swiss Alps, to visit his cousin who is seeking a cure for his tuberculosis in a sanatorium in Davos. What was supposed to be a mere visit turns into a prolonged stay as his departure is repeatedly delayed when Hans develops symptoms of the same disease. For seven years the young man remains in Davos, encountering and learning from a variety of people who engage him in the discussion of ideas ranging from secular humanism to totalitarianism to love. The heady thrill of discovering and nurturing ones own intellect, albeit in a rareified place that is often removed from the real world, and the necessity to return to that world in which our curiosities are tested in the end, should provide useful fodder for the burgeoning mind.

5. Rolling Nowhere (Ted Conover, Vintage, 2001)

As a young undergraduate at Amherst, Ted Conover decided to take a year off and ride the rails, trying to understand the lives of America's hoboes. Equipped with no more than his thrift-store clothing and burdened by his middle-class upbringing, Conover traveled on foot and by rail over most of the Western United States. Over the course of his journey he learns how to survive and how to spring back from adversity, living on hand-outs, sleeping on the lam and staying one step ahead of the railroad police. He also learns about losing everything he has, and about creating identity, and about the salience of experience as a teacher whose wisdom far outweighs that found in books. Learning to immerse oneself in the world one wishes to understand, and the invaluable gift of risk and spontaneity, these are the true badges of courage and those which every young person ought to earn. What better way to figure out how than by hearing it in the voice of someone their own age? And should they get hooked, Conover's books Cayotes: A Journey Across Borders with America's Illegal Immigrants (Vintage, 1987) and New Jack: Guarding Sing-Sing (Vintage, 2001) are also wonderful works that were researched "in-scene" by the author.

6. Multi-Cultural Literacy (Rick Simonson, Scott Walker, Eds. Graywolf Press, 1988)

In the Summer of 2013, I was sitting in my childhood home in Sri Lanka when news came of the verdict against Trayvon Martin. The words that I needed in order to wrest some sense of the tragedy lay in this collection of 13 essays. Writing from thinkers such as James Baldwin,Carlos Fuentes, Michelle Cliff, Paula Gunn Allen, Ishmael Reed, and Wendell Berry, cover a range of voices that are more resonant of the diversity of American life and thought, than what is commonly taught in curriculae across the nation. As James Baldwin says, in his 1963 work, "A Talk To Teachers," "One of the paradoxes of education was that precisely at the point when you begin to develop a conscience, you must find yourself at war with your society. It is your responsibility to change society if you think of yourself as an educated person." For the young person short on time but in great need of that particular education, this is a perfect introduction into both American life, and the art of learning.

So What (Taha Muhammad Ali, translated by Peter Cole, Copper Canyon Press, 2008)

Taha Muhammad Ali is a self-taught writer, one who came to write of that experience, not out of a formal education -- his schooling stopped at fourth grade -- but through his own reading and acknowledgement that writing poetry was the one thing left in his power to do. His poems are a mix of personal memory (of a time past) and a poet's imagination (of a time that might have been), both complicated by an acute awareness of experiencing a collective injustice. It echoes the myriad yearnings of the displaced, the distortions of history noted and questioned, the fragility of private joy embraced with deep strength, and the resiliency of a people's hope for the seemingly impossible someday set down, too, as responsibility and rebellion. In "The Fourth Qasida" he addresses the beloved thus: "Amira!/ When our loved ones leave us,/ as you left,/ an endless migration in us begins,/ and a certain sense takes hold in us/ that all of what is finest/ in and around us,/ except for the sadness,/ is going away./departing, not to return." And yet, despite the ache of those words, when taken as a whole, the So What of the title of this collection of poetry becomes an epiphany: so what that we have lost everything, so what if we may never get any of it back, so what if death is rarely of natural causes, so what? We write anyway. We live anyway. We dream anyway. Surely a moving and powerful message for the young people in our lives into whose hands we pass along the best and the worst of our own history.

8. Wise Latinas: Writers on Higher Education (Jenn de Leon, ed. University of Nebraska Press, 2014)

In a Steinberg Prize-winning essay titled "White Space," editor Jenn de Leon writes of her experience helping her father, a Guatemalan immigrant, to put together his resume. In the blanks left under the usual categories we are accustomed to seeing on a cv, categories her father had no time to fill as he worked to earn a living for his family, she writes of the life he lived as a laborer. The heart behind that essay guides the selections for this anthology of writers as de Leon attempts to give first-generation female graduates a guide to navigating their education. The pressure to value marraige and family over the acquisition of knowledge is parsed by writers ranging from Sandra Cisneros to Julia Alvarez. While the essays ought to be required reading for young Latinas facing the clash between what they've been told and what they now face in their "new" American lives, the book holds relevance for any young person setting out of their homes for the first time.

9. The Unknown University (Roberto Bolaño, translated by Laura Healy, New Directions, 2013)

Hailed by the New York Times as "the most significant Latin American literary voice of his generation," most people are probably unaware of this posthumously published collection of the Chilean writer's work as a young man. It is a book teetering between self-examination and self-realization, an account of finding a way through youth and desire, and a harbinger of the greatness to come. It is, as critic Dwight Garner, writing for the New York Times puts it, "the unrhymed free verse of a man who was equal parts poet and poet manqué, a word-drunk literary drifter still finding his voice... autobiographical, and, like his fiction...filled with starving, wandering, jousting, sex-mad, aggrieved, ego-dented poets and artists." What a lovely brew for the young whose most idiotic and most profound mistakes, as well as their greatest achievements, are still ahead of them!

10. Hyperbole and a Half (Allie Brosh, Touchstone, 2013)

This is the book you place on top of those other nine-ish books you just bought or ordered (from independent booksellers!) It is the book that communicates that you are a savvy aunt/uncle/grandparent/neighbor/parent. This is Allie Brosh, the internet goddess of the young and the rest of us. It proves you are hip and cool and will persuade your particular Young Person to read those other books too, from which they will take frequent breaks to read this one so they can get their daily ab work-out by ROTFL. Allie Brosh, who began her internet musings one night in college when she was trying to avoid studying, has a finger on the pulse of our American human condition. She knows that "Dogs Don't Understand Basic Concepts Like Moving," and she undertands "Adventures in Depression," and can even muse on "Depression Part Two," (which, incidentally are two of the most frequently passed-along meditations on depression). Laughs aside, the line-drawings and insight she offers are priceless in their truth and excess. Who should buy this book? #people. (true confession: I own the "Clean ALL the things?" t-shirt. It's great. Throw that in as a bonus.)

Happy Graduation!