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10 books to read when you're feeling lost and directionless in life

Hiking in Switzerland on Via Alpina trail
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Stand still. The trees ahead and bushes beside you
Are not lost. Wherever you are is called Here,
And you must treat it as a powerful stranger,
Must ask permission to know it and be known.

From "Lost" by David Wagoner, in Traveling Light: Collected and New Poems.

Sometimes life is clear – you know exactly where you're heading and which path you're on. But often it's not that simple.

You might run into a feeling of not being where you want to be in your career, finding yourself frozen in one place, or realising you've got stuck in a rut.

During these times, you can even lose sight of the one thing you thought you knew: yourself. And with that, what you used to enjoy and aspire for.

But, as always, everything you're feeling can usually be found in a book somewhere too.

Here are some of my favourite book recommendations for when you're feeling lost and unsure of where to go next.

Including both fiction and non-fiction, these are some of the books that helped me most when I felt lost, especially when I quit my job, started a business, moved countries, and navigated bouts of depression.

10 books to read when you're feeling lost in life

1. A Prayer for the Crown-Shy (Monk & Robot 2) by Becky Chambers

"Tender and healing... I'm prescribing a preorder to anyone who has ever felt lost. Stunning, kind, necessary," writes author Sarah Gailey about this feel-good book from the author at the forefront of hopeful science fiction.

A Prayer for the Crown Shy is the second book in Becky Chambers' Monk & Robot series, weaving an intriguing world about the robots of Panga who long ago laid down their tools and disappeared into the wilderness after they gained self-awareness.

But one day, a robot startles a tea monk with a question that no one can seem to answer: "what do people need?"

To start at the beginning of the Monk & Robot series, first pick up a copy of the equally uplifting A Psalm for the Wild-Built.

2. Great Circle by Maggie Shipstead

I read Great Circle right at the end of 2021 and was blown away by it. I've been at a fork in the road with my work, trying to steer further in the direction of my creative projects and away from the last of the consulting work I'm doing.

I've been pivoting towards this position over the last few years, but lately I've felt an urge to jump and figure it out afterwards.

If there's a version of me who knows exactly what they want and has the guts to jump at it, she'd be like Marion in Great Circle. I loved this description of her:

"She couldn’t fathom that others did not see her for what she would become, that she did not wear the fact of her future like some eye-catching garment. Her belief that she would fly saturated her world, presented an appearance of absolute truth."

It's not just Marion grappling with who she wants to be in this novel.

Her brother says to their uncle: "You're supposed to be a painter," to which he responds "I've lost the ability". Her brother's retort: "No, [...] you just need to go out into the mountains like you used to.”

This book poses that powerful question in a multitude of ways: what do you need to do like you used to?

3. The Memoirs of Stockholm Sven by Nathaniel Ian Miller

The Arctic is one of my top happy places, and so as soon as I heard about this book I knew I had to read it.

It's the story of Sven, a man who leaves a restless life in Stockholm for a solitary life in the Arctic Circle, where he's saved by good friends, a loyal dog, and a surprise visit that changes everything.

At one point early on in the book, Sven laments:

"Since childhood I had envied those who knew with certainty what course they wished their lives to take. I did not know. I have never known."

Here's the advice he receives, which I noted down and have returned to a few times since reading:

"For now, take stock of yourself. This is the chance you waxed about so long ago. Listen for the voice that speaks when all others go silent. Be alone—be entirely alone. I am not saying you will find anything of worth there—certainly no cosmic truth—but maybe you will begin to feel as pared down, efficient and clean as a freshly whittled stick.”

4. War and Peace by Leo Tolstoy

I shared many years ago about how War and Peace is a fantastic book to read when you're stuck in a rut. Here's one section I still love:

"‘It seems odd,’ said Pierre, ‘that you, you consider yourself a failure and your life ruined. You’ve got your whole life in front of you, everything. And you…’

He did not say what about you, but his tone showed how much he admired his friend, and how much he was expecting from him in the future."

If you'd like to give War and Peace a try, here's my guide to reading it for the first time.

I've also shared my comparison of the best translations, with this clothbound Penguin classic translated by Anthony Briggs as my top choice.

5. Timeless Simplicity: Creative Living in a Consumer Society by John Lane

If there's something you know you want to be doing but you don't yet have the guts to do, Timeless Simplicity has some unexpected snippets of wisdom.

On the surface it's a guide to pursuing more simplicity in your life, but beneath that there's plenty of heartfelt advice on making your life your own.

"And if you don’t make the break now, when will you do so? Change is difficult, but it can be made, and has been by millions before you — millions who have found a way to live the kind of life they want to live, and work the kind of way they want to work."

6. Maybe in Another Life by Taylor Jenkins Reid

Maybe in Another Life is one of Taylor Jenkins Reid's lesser-known novels, unlike her bestselling sensations The Seven Husbands of Evelyn Hugo and Daisy Jones & the Six.

But it's perhaps her best book to read when you're feeling lost in life, just like the twenty-nine-year-old protagonist, Hannah Martin.

After a failed relationship and with no job or house to anchor her, she moves back to Los Angeles, where she once again finds herself at a crossroads.

After bumping into an old flame, we see in alternating chapters two possible scenarios unfold—with very different results.

“You don’t need to find the perfect thing all the time. Just find one that works, and go with it."

7. Keep It Moving: Lessons for the Rest of Your Life by Twyla Tharp

I've loved Twyla Tharp's writing (and pretty much everything about her, really) since I first read The Creative Habit: Learn it and Use it For Life at least a decade ago.

This is her fourth book, in which she shares her wisdom on how to keep moving as you age.

Aged seventy-seven when this book was published, Twyla Tharp is revered not only for the dances she makes as one of the world's leading choreographers, but also for her astounding routines and vitality.

She still hails a taxi at daybreak, hits the gym, and uses that energy to propel her through her commitments. This book answers how.

"Your objective is to free yourself to be whatever and whoever you need to be right now."

8. The Sun is a Compass by Caroline Van Hemert

A glaringly obvious addition to this list would be Wild: A Journey from Lost to Found by Cheryl Strayed. And yes, it is a wonderfully relevant book to read when you're feeling lost and directionless.

But I wanted to share something further off the beaten track, as it were – in this case, deep into Alaska.

The Sun is a Compass is Caroline Van Hemert's memoir of the 4000-mile, human-powered journey she undertook with her partner, Pat, when she was unsure whether to stay in academia or pursue other callings.

It's a stunning book that I've mentioned a lot before – here and on Live Wildly – but it's been one of the rare books to really speak to where I am and hoping to go next.

"I tried to explain that escapism wasn’t our goal—neither of us was running from a broken marriage or drug addiction or academic failure. We weren’t trying to set a record or achieve a first. We were simply trying to find our way home."

9. Killing Commendatore by Haruki Murakami

I wrote about Killing Commendatore in my recent post about books that celebrate the beauty of early mornings.

So adding it here too might offer an excess of Murakami, but rereading this quote reminded me just how apt the book is for when you're feeling lost in life (or finding the courage to start afresh):

“The way I see it,” Menshiki said, “there’s a point in everybody’s life where they need a major transformation. And when that time comes you have to grab it by the tail. Grab it hard, and never let go. There are some people who are able to, and others who can’t. Tomohiko Amada was one who could.”

In the novel, we meet an unnamed portrait painter who retreats to the mountains after a failed relationship and realising the art he's creating isn't what he's really called to do.

As he grapples with this, Murakami poses plenty of questions for ourselves, too, while weaving a magical universe in a way that only he really can.

10. Your Life in Bloom: Musings on Finding Your Path & Your Courage, Grounded in the Wisdom of Nature by Lucy Fuggle

Your Life in Bloom book cover

This is the book I wrote when struggling with depression during Covid-19. I had also found myself at a fork in the road with my work.

It's a short collection of musings on finding your courage, working out where you want to go in life, and taking a bold step forwards.

"There’s never one right path. There are thousands of versions of your life in which you have the most fantastic time. You can never choose all of them. But you can realise when you’re feeling stuck and take a small step in a different direction. Even when you have no idea where you’re going, you can follow your curiosity, just to see where it takes you. You don’t need a calling or grand mission. It’s more than enough to make your life a gentle pursuit of love, joy, and curiosity..."

Other honourable mentions:

The Midnight Library by Matt Haig – The darling book of the quarantine era, this is Matt Haig's imagining of the countless different directions a life can take.

My Year of Rest and Relaxation by Ottessa Moshfegh – A novel about one young woman's efforts to duck the ills of the world by embarking on an extended hibernation with the help of one of the worst psychiatrists in the annals of literature.

Into the Magic Shop: A neurosurgeon's true story of the life-changing magic of mindfulness and compassion by James Doty – A stunning exploration of the ways we can transform our minds when we pay more attention to our thoughts.

Conversations with Friends by Sally Rooney – If you want to read about rather aimless characters figuring out their way, Sally Rooney's writing is the perfect place to start.

I Found My Tribe by Ruth Fitzmaurice – A celebration of the delights of wild swimming and the community you can gain alongside it, here in an Irish town in Co. Wicklow.

Four Thousand Weeks: Time Management for Mortals by Oliver Burkeman – One of my favourite books of 2021, this is a fantastic reminder to reassess the real meaning of time management and spend our time on what really matters to us.

 
 

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