9 Books to Read When You're Feeling Lost

9 Books to Read When You’re Feeling Lost.

Is anyone else kind of obsessed with reading self-help books? I’m in this really tricky-to-navigate phase of life where I’m about to graduate from college with an idea of what I want out of these next few years, but no idea where to start. So many other people have been there, so why not read what they have to say about powering through and making it happen, right? Some self-help books can turn rather preachy, but those on this list are standouts for their power to inspire and motivate without using too many I-statements.

1. “The Big Life: Embrace the Mess, Work Your Side Hustle, Find a Monumental Relationship and Become the Badass Babe You Were Meant to Be” by Ann Shoket, former editor-in-chief of Seventeen and all around badass

Like I said, I’ve read quite a few books of this genre, but none resonated with me the way Shoket’s did. She takes a tone that shows she’s young enough to get it and to care, but experienced enough to actually offer some sound advice on everything from landing your dream job to saying no to a bad date. Better yet, the majority of her sentences don’t start with “I” (as in, “I was EIC of Seventeen, so you best listen up”). Instead, every sentence is about you, you “badass babe” who’s “hustling” through side gigs, Tinder dates and #squad brunches. While the book is targeted at women in the media industry, Shoket made a point of talking to just about every brand of awe-inspiring superwoman you can imagine and their biggest take home messages are the same: be passionate about literally anything, never stop nurturing that flame and let it inspire every corner of your world. Sound good? Pick up a copy of this book and get moving.

2. “Is Everyone Hanging Out Without Me? (And Other Concerns)” by Mindy Kaling, actress, producer, and everyone’s dream BFF

If Kaling lays to rest any big Hollywood secret in this book, it’s that the annoying feeling of FOMO never really fades. But hey, she explains, missing out isn’t all bad. This is a book on self love and self acceptance, fueled by the ability to laugh at all the mishaps along that journey. Kaling gives an honest to goodness look at what it was like growing up as the hilarious drama queen with a goal so much bigger than anyone thought possible. She looks back on her journey with such genuine pride and humility that you can’t help but feel inspired to work even harder and have some more fun. So yes, everyone is probably hanging out without you. But you’ve got big things in the works, too.

3. “The Opposite of Loneliness: Essays and Stories” by Marina Keegan, beautiful writer gone far too soon

“We don’t have a word for the opposite of loneliness,” writes Marina Keegan, “but if we did, I could say that’s what I want in life.” So begins Keegan’s moving collection of short stories and essays written while she was an undergrad at Yale. Keegan died in a car accident in 2012 and the book is a compilation of the work she left behind. Its namesake essay was Marina’s final submission to the Yale Daily News, written on the cusp of graduation with a world of possibilities and “so much time” before her. Both in fiction and nonfiction, she writes confidently with a tone that captures so much of the human spirit at so many stages of life — falling in love for real for the first time, going home from college and finding a void where you once found yourself, pushing a whale back to sea, coming to terms with death, and finding the people that make you feel whole. It’s a book that will encourage you to do what you love without looking back.

9 Books to Read When You're Feeling Lost

4. “The Happiness Project: Or Why I Spent a Year Trying to Sing in the Morning, Clean My Closet, Fight Right, Read Aristotle, and Generally Have More Fun,” by Gretchen Rubin, happiness expert and life’s eternal ray of sunshine

I included the entire title of this book above because it nods to a huge trend in the blog world right now: the idea of making subtle changes to one’s routine that substantially affect one’s happiness. I’m not sure if I buy this idea yet (I’ve probably read 50 posts on how to overhaul my morning routine and I still resent my alarm clock just as much as before), but Rubin explains it’s all about your mindset. It’s about consciously choosing happiness, even when that feels like a chore and even when it feels like just another item on your to-do list. It’s about committing to yourself and taking stock of your overall well being. It’s about deciding to have fun when you can and to grin and bear it when you can’t. And if you haven’t listened to podcast Rubin hosts, called Happier, you ought to give that a try too, it’s one of my favorites.

5. “Tiny Beautiful Things: Advice on Love and Life from Dear Sugar,” by Cheryl Strayed, lover, thinker, adventurer, and solver of everyone else’s problems

I read Cheryl Strayed’s “Wild” back when it was flying off the shelves a few years ago as Reese Witherspoon appeared onscreen in the movie adaptation of Strayed’s decision to hike hundreds of miles through California by herself. I was in high school at the time and decided then that I, too, needed a solo soul-searching journey through the wilderness. But before I can head for the woods with a pack that weighs twice as much as I do, I need to start with the words in “Tiny Beautiful Things.” I’ve always been a sucker for a great advice column and that’s exactly what you’ll find in Tiny Beautiful Things. Strayed wrote advice to strangers under the pen name “Dear Sugar” and some of her best responses are in this book. You’ll come away with a sense of strength and an understanding that there’s always room to work on loving yourself and showing kindness to others.

6. “Overwhelmed: How to Work, Play, and Love When No One Has the Time” by Brigid Schulte, journalist, researcher, and discoverer of how to make more hours in the day

If the title of this book doesn’t make you shoot your hand in the air and scream “me!” I don’t know what will. When Schulte’s life as a journalist began to overwhelm her life as a human being — you know, one with a family and interests outside of work — she decided to stop getting bogged down by the chaos and instead set out to find out why her story is one that’s so familiar to so many people. Turns out, we’re letting stress get the best of us and we’re just not making enough time for anything else. Our culture has turned leisure time into something to be scorned rather than something to be celebrated she discovered upon investigating how other countries approach work-life balance. Much like Ruben, Schulte explains that working, playing and loving are all choices and commitments we have to make everyday in order to live a life we actually enjoy.

9 Books to Read When You're Feeling Lost

7. “Adulting: How to Become a Grown-Up in 468 Easy(ish) Steps” by Kelly Williams Brown, journalist turned expert grown-up

You know those flakes of mascara that pepper your undereyes by the end of the day? Kelly Williams Brown dubs them “failure flakes” in the introduction to her book (complete with an illustration), but then goes on to explain that maybe you shouldn’t use mascara that cakes and crumbles by 5 p.m. anyways and maybe you aren’t such a failure afterall because you did manage to pick up this book! All in all, this is one of those books that’s going to be on my bookshelf for at least the next five years since her 400+ steps to adulthood include everything from what to look for in your first lease to how to apologize to what not to do if you want a great job. If you’ve got a plan for everything and a to-do list to match, this is the book for you.

8. “Bad Feminist: Essays” by Roxane Gay, critical cultural thinker and dream liberal arts professor

This book was part of the required reading for a women’s literature class I took my first year of college and let me tell you: feminism is complicated. I’ve always identified as a feminist, but Gay’s book of essays, most of which are full of intrinsic reflection, made me think critically about the complexity of a value that looks different for everyone. I wondered about ideas like: Is my feminism inclusive? How do feminism and femininity overlap? Is there anything to gain from criticizing how others express feminism and femininity? And what even is women’s literature anyways, isn’t it just literature? Clearly, I may have walked away from this book with more questions than answers. It’s part of being a “bad feminist,” but also part of being a more informed one.

9. “You Are a Badass: How to Stop Doubting Your Greatness and Start Living an Awesome Life,” by Jen Sincero, life coach and believer in power posing, probably

This book consistently tops lists of great self-help books, so of course I had to grab a copy for myself this summer. I didn’t love it the way I did others on this list, but it’s a notable mention for anyone in a stage of life where they just feel bored. Sincero offers tips for becoming your best self by way of embracing your best self. In other words, she’s a big proponent of goal-oriented thinking and acting upon big ideas that will put those goals in motion. Ready for that promotion or need to make a career leap? She’s your girl.

What self help books have you loved and what’s still on your reading list?

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  • When Things Fall Apart by Pema Chodron. It’s timeless in it’s advice and it helped me through some pivotal times when I needed to make big decisions. I can read it one hundred times and pick out something new every time.

  • I stop by this blog every few weeks and catch up on all I’ve missed, and I’m so glad I came across this post. When you wrote “Schulte explains that working, playing and loving are all choices and commitments we have to make everyday in order to live a life we actually enjoy” it was basically all I needed to hear [read] in order to be convinced to buy that book. Thank you for sharing all these!