100 books like The Rules Do Not Apply

By Ariel Levy,

Here are 100 books that The Rules Do Not Apply fans have personally recommended if you like The Rules Do Not Apply. Shepherd is a community of 11,000+ authors and super readers sharing their favorite books with the world.

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Book cover of Lands of Lost Borders: A Journey on the Silk Road

Maggie Shipstead Author Of Great Circle

From my list on female adventurers.

Why am I passionate about this?

In my third novel, Great Circle, a fictional aviator named Marian Graves disappears while trying to fly around the world north-south in 1950. While researching and writing, I became a travel journalist, partly so I could follow my character into far-flung, rugged corners of the world. Traveling, I encountered people who lead truly adventurous lives, and I started to seek out riskier experiences myself. I swam with humpback whales, tracked snow leopards in the Himalayas, and journeyed across huge seas to Antarctica’s Ross Ice Shelf. I still don’t consider myself a full-fledged adventurer, but I love reading about women contending with the challenges of wild places and their own internal landscapes.

Maggie's book list on female adventurers

Maggie Shipstead Why did Maggie love this book?

I’m more of a spin class person than a “cycle thousands of miles through Central Asia” person, but I loved reading about Kate Harris’s months tracing the Silk Road by bicycle in 2011. She doesn’t sugarcoat the hardships of such an undertaking (rain, snow, mountains, traffic, logistics, bureaucracy, scary humans, forbidden Chinese border crossings, friction with the friend who’s riding with her), which makes her human as well as brave, tough, funny, and brilliant. Books like this make huge travel projects seem possible, and even if I’ll never do anything on this scale, I love imagining such epic experiences.

By Kate Harris,

Why should I read it?

2 authors picked Lands of Lost Borders as one of their favorite books, and they share why you should read it.

What is this book about?

"Lands of Lost Borders carried me up into a state of openness and excitement I haven't felt for years. It's a modern classic."-Pico Iyer

A brilliant, fierce writer, and winner of the 2019 RBC Taylor Prize, makes her debut with this enthralling travelogue and memoir of her journey by bicycle along the Silk Road-an illuminating and thought-provoking fusion of The Places in Between, Lab Girl, and Wild that dares us to challenge the limits we place on ourselves and the natural world.

As a teenager, Kate Harris realized that the career she craved-to be an explorer, equal parts swashbuckler and…


Book cover of Wild: From Lost to Found on the Pacific Crest Trail

Jim Landwehr Author Of Dirty Shirt: A Boundary Waters Memoir

From my list on the trials and joys of outdoor adventure.

Why am I passionate about this?

I have been a lover of all things outdoors since I was a boy. After my father was killed at a young age, my brothers and I took his love for outdoor adventure and made it our own. Fully aware of all that can go wrong, my brothers and I went into our ventures with a keen sense of humor. Camping, fishing, and kayaking all come with their own challenges and requisite hilarious moments. It is these moments of adversity, and personal risk, that are sometimes lightened by a good dose of laughter and levity.

Jim's book list on the trials and joys of outdoor adventure

Jim Landwehr Why did Jim love this book?

Much like A Walk in the Woods, Wild takes an ordinary person and puts them in an extremely challenging environment only to show they were unprepared for the rigors of the great outdoors.

Strayed has a similar goal to Bryson, but chooses the Pacific Crest Trail. The hike is an attempt at self-discovery as well as to challenge herself after experiencing various addictions and the loss of her mother. Strayed’s motives are not unlike those of my brothers and I as we ventured into the BWCAW while navigating our young lives as twenty-somethings.

By Cheryl Strayed,

Why should I read it?

27 authors picked Wild as one of their favorite books, and they share why you should read it.

What is this book about?

#1 NEW YORK TIMES BESTSELLER • A powerful, blazingly honest memoir: the story of an eleven-hundred-mile solo hike that broke down a young woman reeling from catastrophe—and built her back up again.

At twenty-two, Cheryl Strayed thought she had lost everything. In the wake of her mother’s death, her family scattered and her own marriage was soon destroyed. Four years later, with nothing more to lose, she made the most impulsive decision of her life. With no experience or training, driven only by blind will, she would hike more than a thousand miles of the Pacific Crest Trail from the…


Book cover of The Remains of the Day

Victor Lodato Author Of Honey

From my list on packing an emotional punch.

Why am I passionate about this?

In addition to writing novels, I’m also a playwright. Whatever form I work in, I’m drawn to character, drama, and emotion. I aspire to write literary page-turners that feel as rich and complicated as real life.  Also, I want the endings of my books to slay readers and break their hearts. Of course, when I say that, I’m not necessarily speaking of sorrow; sometimes your heart breaks from expanding, from a surfeit of feeling. Your heart breaks only to grow larger.

Victor's book list on packing an emotional punch

Victor Lodato Why did Victor love this book?

This novel about an English butler’s lifetime of service and his friendship with the housekeeper, Miss Kenton, is an absolute stunner.

Near the end of the book, when the butler and the housekeeper run into each other again, years after their service to Lord Darlington, the scene is expertly understated. 

This book doesn’t give in to trite sentimentality, but rather, it moves you by its keen understanding of human nature.

By Kazuo Ishiguro,

Why should I read it?

13 authors picked The Remains of the Day as one of their favorite books, and they share why you should read it.

What is this book about?

*Kazuo Ishiguro's new novel Klara and the Sun is now available to preorder*

The Remains of the Day won the 1989 Booker Prize and cemented Kazuo Ishiguro's place as one of the world's greatest writers. David Lodge, chairman of the judges in 1989, said, it's "a cunningly structured and beautifully paced performance". This is a haunting evocation of lost causes and lost love, and an elegy for England at a time of acute change. Ishiguro's work has been translated into more than forty languages and has sold millions of copies worldwide.

Stevens, the long-serving butler of Darlington Hall, embarks on…


Book cover of Annapurna: A Woman's Place

Cathryn J. Prince Author Of Queen of the Mountaineers: The Trailblazing Life of Fanny Bullock Workman

From my list on barrier breaking women.

Why am I passionate about this?

I have loved writing since I was in grade school and after graduating university with a degree in International Affairs I became a journalist. I’ve written six non-fiction books and also teach Journalism at SUNY Purchase.  I’ve always been fascinated about the way one person’s life or one seemingly small episode in history allows us a way to examine the larger picture: whether it was how Fanny Bullock Workman showed what it meant to be a woman in a predominantly male world of mountain climbing or how the deliberate sinking of the Wilhelm Gustloff in the closing days of WWII showed that war is never black and white, that there are layers to people and stories and events that we should always try to consider.

Cathryn's book list on barrier breaking women

Cathryn J. Prince Why did Cathryn love this book?

It illustrates how one woman’s courage to forge ahead in a male-dominated world produced scientific work that challenged gender stereotypes and led to all-male clubs breaking their male-only rules.

By Arlene Blum,

Why should I read it?

1 author picked Annapurna as one of their favorite books, and they share why you should read it.

What is this book about?

In August 1978, thirteen women left San Francisco for the Nepal Himalaya to make history as the first Americans—and the first women—to scale the treacherous slopes of Annapurna I, the world’s tenth highest peak. Expedition leader Arlene Blum here tells their dramatic story: the logistical problems, storms, and hazardous ice climbing; the conflicts and reconciliations within the team; the terror of avalanches that threatened to sweep away camps and climbers.

On October 15, two women and two Sherpas at last stood on the summit—but the celebration was cut short, for two days later, the two women of the second summit…


Book cover of A Field Guide to Getting Lost

Virginia Rademacher Author Of Derivative Lives: Biofiction, Uncertainty, and Speculative Risk in Contemporary Spanish Narrative

From my list on combating post-truth contagions.

Why am I passionate about this?

I’m a writer and professor of literary studies whose work has been deeply involved in topics of truth, realism, and public policy. My recent book considers works of fiction that openly and honestly experiment with questions of uncertainty, identity, and risk in the supermodern present. This book draws from disciplinary discourses in law, finance, and economics, which similarly contend with competing claims to truth and value and dive deep into the circumstantial and speculative games that authors play when they write fiction about reality. I have my PhD in Spanish Literature (UVA), M.A. in International Affairs and Economics (Johns Hopkins Univ.), and a B.A. from Harvard University.

Virginia's book list on combating post-truth contagions

Virginia Rademacher Why did Virginia love this book?

I love the idea that part of how we understand the world is the willingness not to know where we are going or to have the map fully charted beforehand–in effect, the willingness to become lost. Without becoming lost, all our worlds become algorithms with predetermined results.

I found Solnit’s argument that we have increasingly programmed our children (and selves) and no longer risk the freedom to roam and get lost (all in the name of safety) a powerful and compelling metaphor for the tradeoffs we have made in our society.

That people are increasingly siloed and we don’t communicate well across differences of opinion and belief is perhaps not surprising. We stay safely in our zone. We don’t risk getting lost or what we might discover if we traipsed beyond our comfortable assumptions and limits. 

By Rebecca Solnit,

Why should I read it?

2 authors picked A Field Guide to Getting Lost as one of their favorite books, and they share why you should read it.

What is this book about?

In this investigation into loss, losing and being lost, Rebecca Solnit explores the challenges of living with uncertainty. A Field Guide to Getting Lost takes in subjects as eclectic as memory and mapmaking, Hitchcock movies and Renaissance painting.

Beautifully written, this book combines memoir, history and philosophy, shedding glittering new light on the way we live now.


Book cover of One Day

Paul Carnahan Author Of How Soon Is Now?

From my list on time as the lead character.

Why am I passionate about this?

I’m an incurable nostalgist and, thanks to early exposure to a curly-haired, scarf-wearing eccentric who travels the universe in a battered old police box, gained an early and ongoing obsession with time travel stories, whether intricately-plotted and filled with brain-tangling paradoxes, or steeped in wistful yearning for days gone by. Young me would, I like to think, be delighted to learn that he would, one day, write a book bursting with both paradoxes AND yearning.

Paul's book list on time as the lead character

Paul Carnahan Why did Paul love this book?

Time is at the very heart of this book, and I adored the structure of it, relishing the chance to drop in on the lives of Emma and Dexter each July 15 over two decades. It’s a brilliant storytelling conceit, allowing Nicholls to present a series of snapshots of an ebbing and flowing relationship that builds into an emotionally affecting whole.

By the end, I felt like I had spent time not with two characters but with two very familiar people–flawed, frustrating, unpredictable, but always believable, always understandable.

By David Nicholls,

Why should I read it?

3 authors picked One Day as one of their favorite books, and they share why you should read it.

What is this book about?

'ONE DAY is destined to be a modern classic' - Daily Mirror Twenty years, two people, ONE DAY. The multi-million copy bestseller that captures the experiences of a generation. 'I can imagine you at forty,' she said, a hint of malice in her voice. 'I can picture it right now.' He smiled without opening his eyes. 'Go on then.' 15th July 1988. Emma and Dexter meet for the first time on the night of their graduation. Tomorrow they must go their separate ways. So where will they be on this one day next year? And the year after that? And…


Book cover of Bittersweet: How Sorrow and Longing Make Us Whole

Laura Boggess Author Of The Honey Field

From my list on transform grief and loss into something beautiful.

Why am I passionate about this?

As a licensed therapist with a master’s degree in clinical psychology, I’ve helped individuals traverse grief and loss for over thirty years. But when my father passed away last year, I found myself feeling untethered, adrift in a barrage of emotions. In grief, I became more affected by even the smallest glimpse of beauty. The poem that perfectly voiced my heart. The spotted fawn appearing on the edge of the lawn. The purple of the eggplant flowering. Grief slowed me down, opening my eyes to the wonder of this achingly beautiful world we live in. It has become part of my story to endeavor to help others do the same. 

Laura's book list on transform grief and loss into something beautiful

Laura Boggess Why did Laura love this book?

This book gave me a new framework from which to view my grief—one that encouraged me to embrace all the new places inside of me the sorrow seemed to create.

Cain’s research reveals how people who fully allow themselves to experience sorrow often unlock a door to increased creativity, wisdom, and inner peace. Truly a paradigm shifter.

By Susan Cain,

Why should I read it?

5 authors picked Bittersweet as one of their favorite books, and they share why you should read it.

What is this book about?

AN OPRAH BOOK CLUB PICK

THE #1 NEW YORK TIMES BESTSELLER -- FROM THE AUTHOR OF THE INTERNATIONAL BESTSELLER QUIET: THE POWER OF INTROVERTS IN A WORLD THAT CAN'T STOP TALKING

In her inspiring new masterpiece, the author of the bestselling phenomenon Quiet describes her powerful quest to understand how love, loss and sorrow make us whole - revealing the power of a bittersweet outlook on life.

Bittersweetness is a tendency towards states of longing, poignancy and sorrow; an acute awareness of passing time; and a curiously piercing joy at the beauty of the world. It recognizes that light and…


Book cover of His Only Wife

Liz Amos Author Of All the Truths Between Us

From my list on helping you seize the day.

Why am I passionate about this?

Growing up, no one needed to tell me that I’m a highly sensitive person – although they did. The label was confusing: was it a bad thing? I wasn’t sure. So, I tried to keep myself in check and followed my love of words into a legal career. Other people’s books became my refuge: a safe place to explore the full reach of my empathy and find connection. Reading still gives me sanctuary. Only now, since leaving law to become an author and poet myself, I also embrace the emotional rollercoaster of sharing my own creativity. It’s balm for my bittersweet soul.

Liz's book list on helping you seize the day

Liz Amos Why did Liz love this book?

Developing alongside Afi Tekple through this book was like spending time with an inspirational cousin.

Despite being in my mid-thirties, I frequently feel like I’m just beginning to shake off external expectations and live my own life. Unlike Afi, my scenarios don’t involve marrying a man I’ve never met for the sake of my family. But constantly striving to “do the right thing” – as defined by others – has been an emotional burden.

I loved this sensitively written, funny, sensual portrayal of a woman locating her own inner compass. It helped me believe that speaking up for the contours of my existence – and even disappointing a few people along the way – is healthy. Inevitably, some things are lost as a result. But there’s also much to be gained.

By Peace Adzo Medie,

Why should I read it?

1 author picked His Only Wife as one of their favorite books, and they share why you should read it.

What is this book about?

A feelgood debut set in modern-day Ghana, about fashion and finding your voice

'Vivid, witty and utterly absorbing.' Daily Mail

In one of the most talked about and hilarious debuts of the year, Afi Tekple, a bright young seamstress from a small town in Ghana, is convinced by her family to marry a man she has never met.

Elikem Ganyo is a wealthy businessman whose family has chosen Afi in the hope that she will distract him from a relationship with another woman they think is inappropriate.

The fact that she doesn't know Elikem seems a small price to pay…


Book cover of Everybody (Else) Is Perfect: How I Survived Hypocrisy, Beauty, Clicks, and Likes

Alyssa Hardy Author Of Worn Out: How Our Clothes Cover Up Fashion's Sins

From my list on style.

Why am I passionate about this?

Fashion has been the love of my life since I was a little kid pouring over magazines and watching shows on fashion TV in the middle of the night. But I’ve always known fashion is not about clothing, its about feeling and it’s about people. That’s why I love to read the stories about people who work in fashion, who have been impacted by fashion and those who love it just as much as I do. 

Alyssa's book list on style

Alyssa Hardy Why did Alyssa love this book?

Everybody (Else) Is Perfect is a memoir about the author, but it speaks to the ways fashion and beauty have created impossible standards for us all to live by.

Korn was the editor-in-chief of NYLON, which from the outside seems like one of the most glamorous jobs in the world. But, as she details, things are not always as they seems. While brands and magazines promote body positivity and feminism on the inside they’re doing anything but. 

By Gabrielle Korn,

Why should I read it?

1 author picked Everybody (Else) Is Perfect as one of their favorite books, and they share why you should read it.

What is this book about?

From the former editor-in-chief of Nylon comes a provocative and intimate collection of personal and cultural essays featuring eye-opening explorations of hot button topics for modern women, including internet feminism, impossible beauty standards in social media, shifting ideals about sexuality, and much more.

Gabrielle Korn starts her professional life with all the right credentials. Prestigious college degree? Check. A loving, accepting family? Check. Instagram-worthy offices and a tight-knit group of friends? Check, check. Gabrielle’s life seems to reach the crescendo of perfect when she gets named the youngest editor-in-chief in the history of one of fashion’s most influential publication. Suddenly…


Book cover of Simply the Best

Kay Acker Author Of Leaving's Not the Only Way to Go

From my list on sapphic about finding happiness in hard times.

Why am I passionate about this?

I believe deeply that, as messy and painful as life is, there is always joy, and usually humor, to be found. The book I wrote, Leaving’s Not the Only Way to Go, pulls from some of the painful experiences I’ve had, and I often find myself following my description of the book, about two women who meet in a grief group, with “but it’s not a downer!” It’s true, because Leaving is also inspired by all the joy and connections I’ve made for myself, even in the midst of loss. I learned how to balance the two sides of life through books like the ones on this list. 

Kay's book list on sapphic about finding happiness in hard times

Kay Acker Why did Kay love this book?

Simply the Best is a romance set after the COVID-19 pandemic began, and it doesn’t flinch from the pain that era has inflicted on us all. Kallmaker set out to grapple with the question of how we find joy and love after experiencing such devestation, and why trying to find joy and love at all still matters.

This romance is, despite its serious circumstances, as funny and pleasurable as all Kallmaker novels are. 

By Karin Kallmaker,

Why should I read it?

1 author picked Simply the Best as one of their favorite books, and they share why you should read it.

What is this book about?

Simply the Worst…Alice Cabot’s only great love is science, but a lapse in judgment has exiled the New York journalist to the glitzy Gallerias and vapid bubble-babble of Beverly Hills. The assignment to do a flattering feature series on Simply the Best and the superficial nonsense it sells threatens to crush what little is left of her spirit.

Simply the Best...Pepper Addington can’t believe she’s moved up from grunt intern to personal assistant for Helene Jolie, the celebrity socialite founder of SimplytheBest.com. Succeeding at the job she worked so hard to get is her only priority. Keep a cynical know-it-all…


5 book lists we think you will like!

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