Books for figuring out what to do with the rest of your life

For years, Cheryl Strayed wrote an advice column for TheRumpus.net called "Dear Sugar." Strayed wrote anonymously—to her readers she was only "Sugar"—and she answered likewise anonymous letters about love and romance, grief and loss, money and family troubles. To call these "columns" seems to sell them short: these are beautiful, heartfelt, brutally honest essays that go in directions you don't expect. Strayed is compassionate with her letter writers, giving them gentle advice while not pulling any punches, but says her real mission isn't to tell them what they "should" do. Instead, she tries to reveal a third way by either presenting a perspective that those who write can't see on their own, or to complexly hash out what's really going on in their life and situation. My favorite essays, hands-down, are The Ghost Ship That Didn't Carry Us and The Obliterated Place. Proceed with caution: this has a hefty f-bomb count and triggers galore, but it's too good to leave out.
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From the publisher: "In May 2012, bestselling author Neil Gaiman stood at a podium at Philadelphia’s University of the Arts to deliver the commencement address. For the next nineteen minutes he shared his thoughts about creativity, bravery, and strength: he encouraged the students before him to break rules and think outside the box. Most of all, he encouraged the fledgling painters, musicians, writers, and dreamers to make good art."
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I have confidence in Meg Jay, author of The Defining Decade, who says, "Twentysomethings who are looking for a silver bullet will find it here in the form of 468 silver pellets. Without a doubt, one (or a hundred) of these pellets will change your relationship or your career or your mind or your potatoes, all of which matter in adulthood."
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From the publisher: "Our 'thirty-is-the-new-twenty' culture tells us the twentysomething years don't matter. Some say they are a second adolescence. Others call them an emerging adulthood. Dr. Meg Jay, a clinical psychologist, argues that twentysomethings have been caught in a swirl of hype and misinformation, much of which has trivialized what is actually the most defining decade of adulthood. Drawing from a decade of work with hundreds of twentysomething clients and students, THE DEFINING DECADE weaves the latest science of the twentysomething years with behind-closed-doors stories from twentysomethings themselves. The result is a provocative read that provides the tools necessary to make the most of your twenties, and shows us how work, relationships, personality, social networks, identity, and even the brain can change more during this decade than at any other time in adulthood-if we use the time wisely."
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From the publisher: "Rachel Friedman has always been the consummate good girl who does well in school and plays it safe, so the college grad surprises no one more than herself when, on a whim (and in an effort to escape impending life decisions), she buys a ticket to Ireland, a place she has never visited. There she forms an unlikely bond with a free-spirited Australian girl, a born adventurer who spurs Rachel on to a yearlong odyssey that takes her to three continents, fills her life with newfound friends, and gives birth to a previously unrealized passion for adventure. As her journey takes her to Australia and South America, Rachel discovers and embraces her love of travel and unlocks more truths about herself than she ever realized she was seeking."
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I'm usually not a fan of gift books, but I'll make an exception for Sandberg's game-changing bestseller about making the choices necessary for long-term success early in your career. This edition has been updated with specific advice aimed squarely at new college grads.
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Hewitt writes with high school graduates and college entrants in mind, covering topics such as building your resumé with extracurricular activities, finding mentors, and forming your character. I like this book because of its specific, practical advice I've not encountered elsewhere: "When you graduate, move to one of the three major cities; do not obtain your graduate degree from the same university as your B.A.; avoid courses where the reading list is dominated by titles published within the last three decades; do study history." This book is targeted to a Christian audience, and contains chapters on choosing a church. Add Audible narration for $3.99.
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When I graduated in the '90s, Dr. Seuss's Oh, the Places You’ll Go! was a clever, quirky pick for the new graduate. No longer. This classic has been marketed to death: don’t even think about buying this (unfairly) tired-out book for your graduate. Instead, try this lesser-known Dr. Seuss classic. It's out of print, but it shouldn't be too hard to find a copy–and it's well worth it. (Warning: brace yourself for a terrible ending. It's worth reading anyway.)
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