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11 Hauntingly Beautiful Cheryl Strayed Quotes That Will Reverberate With The Free-Spirited You

Cheryl Strayed has been my inspiration from the time I didn’t even know who she was. I was one of those millions who had their hopes and lives pinned on Sugar, an anonymous writer who absorbed stories of strangers, and advised them through letters at TheRumpus.net. I was in college back then, and I remember rushing back home every evening, because by the time I had discovered this fabulous lady, she had already written a bunch of advises. I would make myself a cup of mean coffee, and sit with my notebook for hours, crying to a point when I wouldn’t be able to say whether those tears where ones of delight or of terrible pain. There was something about Sugar that compelled me (like many others) to run towards darkness because that’s where you shine; she lay herself bare, she encouraged to embrace vulnerability, she was fearless, she was a radical empathizer.

When I found out Sugar was Cheryl Strayed, the author of books like, Torch and Wild, I had to read her books and each word written by this woman, because whatever she spins is literary art. Cheryl Strayed is an artist. As Steve Almond puts it,

“She (Cheryl) is able to transmute the raw material of the self-help aisle into genuine literature.”

Recently, my boyfriend gifted me Tiny Beautiful Things, a hand-picked collection of Dear Sugar columns. Reading those letters, for the second time, I am certain that Cheryl Strayed is a treasure; she is the person we all ought to be… or maybe who we all are, at the core, but are too afraid to be!


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Here are 11 Cheryl Strayed quotes that will offer you compassion and courage, wisdom and hope, love and the audacity to be yourself.

1. “I’ll never know, and neither will you, of the life you don’t choose. We’ll only know that whatever that sister life was, it was important and beautiful and not ours. It was the ghost ship that didn’t carry us. There’s nothing to do but salute it from the shore.” ― Cheryl Strayed, Tiny Beautiful Things: Advice on Love and Life from Dear Sugar

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Instead of mulling over how wonderful your life could have been, cherish it as your creation, something brilliant that is still in the making.

2. “I knew that if I allowed fear to overtake me, my journey was doomed. Fear, to a great extent, is born of a story we tell ourselves, and so I chose to tell myself a different story from the one women are told. I decided I was safe. I was strong. I was brave. Nothing could vanquish me.” ― Cheryl Strayed, Wild: From Lost to Found on the Pacific Crest Trail

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What you tell yourself you are, you become. Remind yourself, on a daily basis, how beautiful, brave and smart you are.

3. “Nobody will protect you from your suffering. You can’t cry it away or eat it away or starve it away or walk it away or punch it away or even therapy it away. It’s just there, and you have to survive it. You have to endure it. You have to live through it and love it and move on and be better for it and run as far as you can in the direction of your best and happiest dreams across the bridge that was built by your own desire to heal.” ― Cheryl Strayed, Tiny Beautiful Things: Advice on Love and Life from Dear Sugar

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No one will come to save you, sweetpea. You are your knight in shining armor.

4. “Alone had always felt like an actual place to me, as if it weren’t a state of being, but rather a room where I could retreat to be who I really was.” ― Cheryl Strayed, Wild: From Lost to Found on the Pacific Crest Trail

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Being alone is essential. It brings you closer to yourself. Do not mistake it for being lonely, though.


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5. “The useless days will add up to something. The shitty waitressing jobs. The hours writing in your journal. The long meandering walks. The hours reading poetry and story collections and novels and dead people’s diaries and wondering about sex and God and whether you should shave under your arms or not. These things are your becoming.” ― Cheryl Strayed, Tiny Beautiful Things: Advice on Love and Life from Dear Sugar

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And if these things are your becoming, choose them correctly. As Dumbledore would put it, “It is our choices, Harry, that show what we truly are, far more than our abilities.”

6. “I think it’s neat you do what you want. Not enough chicks do that, if you ask me–just tell society and their expectations to go f*ck themselves. If more women did that, we’d be better off.” ― Cheryl Strayed, Wild: From Lost to Found on the Pacific Crest Trail

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Women need to stop belittling each other, and become one another’s inspiration; from whom everyone can draw strength.

7. “You cannot convince people to love you. This is an absolute rule. No one will ever give you love because you want him or her to give it. Real love moves freely in both directions. Don’t waste your time on anything else.” ― Cheryl Strayed, Tiny Beautiful Things: Advice on Love and Life from Dear Sugar

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This is one of the Cheryl Strayed quotes that reminds us why we need her more than anything else! Sugar is tender but she will never sugarcoat. She is the parent, the lover, the friend everyone should aspire to be.

8. “You give a lot of great advice about what to do. Do you have any advice of what not to do?

Don’t do what you know on a gut level to be the wrong thing to do. Don’t stay when you know you should go or go when you know you should stay. Don’t fight when you should hold steady or hold steady when you should fight. Don’t focus on the short-term fun instead of the long-term fall out. Don’t surrender all your joy for an idea you used to have about yourself that isn’t true anymore. Don’t seek joy at all costs. I know it’s hard to know what to do when you have a conflicting set of emotions and desires, but it’s not as hard as we pretend it is. Saying it’s hard is ultimately a justification to do whatever seems like the easiest thing to do—have the affair, stay at that horrible job, end a friendship over a slight, keep loving someone who treats you terribly. I don’t think there’s a single dumbass thing I’ve done in my adult life that I didn’t know was a dumbass thing to do while I was doing it. Even when I justified it to myself—as I did every damn time—the truest part of me knew I was doing the wrong thing. Always. As the years pass, I’m learning how to better trust my gut and not do the wrong thing, but every so often I get a harsh reminder that I’ve still got work to do.” ― Cheryl Strayed, Tiny Beautiful Things: Advice on Love and Life from Dear Sugar

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I am sure you are writing this one down. I have revisited this quote so many times in my life, in so many different situations, different moods, and every time it has offered me something to hold on to, something to aspire for. That’s the magic of Sugar’s words.

9. “You don’t have to get a job that makes others feel comfortable about what they perceive as your success. You don’t have to explain what your plan to do with your life. You don’t have to justify your education by demonstrating its financial rewards. You don’t have to maintain an impeccable credit score. Anyone who expects you to do any of those things has no sense of history of economics or science or the arts.” ― Cheryl Strayed, Tiny Beautiful Things: Advice on Love and Life from Dear Sugar

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YOU DON’T HAVE TO ‘FIT IN’.


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10. “Your assumptions about the lives of others are in direct relation to your naïve pomposity. Many people you believe to be rich are not rich. Many people you think have it easy worked hard for what they got. Many people who seem to be gliding right along have suffered and are suffering. Many people who appear to you to be old and stupidly saddled down with kids and cars and houses were once every bit as hip and pompous as you.” ― Cheryl Strayed, Tiny Beautiful Things: Advice on Love and Life from Dear Sugar

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In a world that lives virtually, this advice is ‘Godspeak’!

11. “I can’t say when you’ll get love or how you’ll find it or even promise you that you will. I can only say you are worthy of it and that it’s never too much to ask for it and that it’s not crazy to fear you’ll never have it again, even though your fears are probably wrong. Love is our essential nutrient. Without it, life has little meaning. It’s the best thing we have to give and the most valuable thing we receive. It’s worthy of all the hullabaloo.” ― Cheryl Strayed, Tiny Beautiful Things: Advice on Love and Life from Dear Sugar

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I had to end with this (why did I have to end, though?!).

Love fiercely and fearlessly.

That’s a wrap from us on Cheryl Strayed quotes. For more quotes on love and life, sign up for our daily newsletter today! So long! 

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11 Hauntingly Beautiful Cheryl Strayed Quotes That Will Reverberate With the Free-Spirited You
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Here are 11 Cheryl Strayed quotes that will offer you compassion and courage, wisdom and hope, love and the audacity to be yourself.
Riya Roy

Riya Roy

“If my doctor told me I had only six minutes to live, I wouldn't brood. I'd type a little faster.” This Isaac Asimov line, embraces my love for writing in the finest and most desperate way that it is and should be! I was tormented by the earnestness of the written word not very early in my journey. But once smitten, it has helped me devour life twice over; savoring the moment and indulging in its memories. As a flâneuse, I wander to understand the intricacies of human relationships. Realizing that, they are just different manifestations of the same feeling of love, has been my greatest learning. I seek to share its opulence through the words I type.