5 Books That Will Help You Through Bad Times

The Cure for a Broken Heart

Tiny Beautiful Things by Cheryl Strayed

“Most things will be okay eventually, but not everything will be. Sometimes you’ll put up a good fight and lose. Sometimes you’ll hold on really hard and realize there is no choice but to let go. Acceptance is a small, quiet room,” writes Cheryl Strayed in one of about a thousand passages you’ll find yourself underlining as you read Tiny Beautiful Things.

Strayed offers the comfort we all need when we find ourselves alone after a failed marriage or a relationship with someone we hoped would love us and didn’t. Her tone is comforting and affirming. She often addresses readers as “sweet peas.” But then she goes one better and pushes us forward, out of despair and back into hope with gentle but firm gems like, “Self-pity is a dead-end road. You make the choice to drive down it. It’s up to you to decide to stay parked there or to turn around and drive out.”

So if you’re pining for a lost or broken love, here’s your prescription: A cup of hot tea (with or without a little bourbon … heartbreak is tough stuff), a cozy chair, and this book. After you read it, I promise you will feel, if not healed, then at least not alone.

Want more like this? Try Wild: From Lost to Found on the Pacific Coast Trail, also by Cheryl Strayed.

The Cure for Idealizing Your 20s

Replay by Ken Grimwood

If you’re one of the Replay fans who read this book when it was first published back in 1986, then you’re lucky. I only recently discovered it, but in a way, I’m glad I didn’t read it until now. It’s the perfect book for your 40s, especially if you suffer those all-too-common pangs of regret about past choices.

See, in Replay, we watch 43-year-old Jeff Winston inexplicably wake up as an 18-year-old … over and over and over again. Each time he tries on a different life, sometimes starting from scratch, other times rewriting old endings, and often making a killing in the stock market. At first, it’s exhilarating to experience it anew with him, and you can’t help but think what you would do if you could relive that time in your own life.

The book manages to keep each “replay” fresh, but by the end, you couldn’t pay me enough to be 18 again. Sure, it was fun, but my 20s were also exhausting. They were full of mistakes, but all my past choices—the good, the bad, the absurdly disastrous—have led me where I am today. I wouldn’t trade that for all the replays in the world. Here’s betting that you’ll feel the same when you read Replay.

Need more convincing? Try Life After Life by Kate Atkinson.

The Cure for Letting Yourself Go

Better Than Before by Gretchen Rubin

Look, none of us is 25 anymore. By your 40s, chances are that you’ve developed a few bad habits, or, like me, failed to develop good ones. I have read a lot of books on self-improvement— diet books, health books, productivity books. Most of them offer a nugget of wisdom, a tip or two that I cling to for a week or two after I put the book down, but none of them has changed the way I think as much as Better Than Before.

With an engaging mix of psychology, motivation, and personal experience, happiness guru Gretchen Rubin helps us identify what we want to improve, understand why we have failed before, and carve out a clear path to success. Here’s why it works: rather than preaching one strategy for changing behavior, she helps the readers craft their own by understanding their natural tendencies.

Simply discovering that I am an Obliger (someone who meets outside expectations but struggles to meet goals I set for myself) changed the way I think about my behavior. Instead of getting frustrated that I don’t exercise enough, I now enlist friends to make me go. I still hate every minute, but I don’t hate myself afterward.

Another good bet? The Happiness Project, also by Gretchen Rubin.

The Cure for Giving Up on Your Dreams:

The War of Art by Steven Pressfield and Shawn Coyne

The best way to describe this book is to quote the Esquire review cited on the cover: “a kick in the ass.” Fiction author Steven Pressfield wrote this book to help wannabe writers, artists, and other unfulfilled types get past their “inner barriers to creativity.” At first, that sounded a bit too squishy for me, but it came highly recommended by my manliest work buddy, so I gave it a chance.

It’s a quick read—some “chapters” are only a paragraph—but a thought-provoking one. As an editor who has always wanted to be a full-time writer, it hit me pretty hard. Why haven’t I written a book yet? Pressfield gets me—he was just like me once—and he sets out in pointed, sometimes harsh language exactly why this happens (he calls it “resistance”) and what it takes to get past it.

I finished the book determined not to give into my usual excuses and delay tactics and just write. If there’s anything you regret not having accomplished, give this book a read. As Pressfield puts it, “If you find yourself asking, ‘Am I really a writer? Am I really an artist?’ chances are you are.” Now go out and do it.

Another inspirational book for aspiring whatevers? Bird by Bird: Some Instructions on Writing and Life by Anne Lamott.

The Cure for Losing Loved Ones

Stitches: A Handbook on Meaning, Hope and Repair by Anne Lamott

By now, most of us have lost a parent, a friend, or someone else we cherished. If you have, you know there’s no cure but time and tears. To keep you company through it (and help you hold on to a shred of faith in the world), you couldn’t do better than Anne Lamott. Lamott knows grief inside and out, having lost her dear friend Pammy, her father, and so many others that regular readers start to wonder why she’s been so unfairly affected.

But while her writing is unflinchingly raw and honest, it’s also uplifting and optimistic and comes with a side of wry humor. “We live stitch by stitch, when we’re lucky,” Lamott writes about loss. “And maybe the stitching is crude, or it is unraveling, but if it were precise, we’d pretend that life was just fine and running like a Swiss watch. This is not helpful if on the inside our understanding is that life is more often a cuckoo clock with rusty gears.”

You could do worse than to let Ms. Lamott hold your hand while you wait to get to the other side. It takes time. Maybe more time than it takes to read this slim volume. Thankfully, Anne has written a number of titles in the same vein, all worth your time. Trust me here. I’ve read them all, at least twice.

See also: Traveling Mercies, Plan B, Grace (Eventually), and Small Victories—heck, anything Ms. Lamott has ever written.