Cheryl Strayed on the art of radical advice giving


Candice Chung

Author Cheryl Strayed

Author Cheryl Strayed Photo: Jonathan Leibson

If there was a literary version of mix-tapes for heartbreak, author Cheryl Strayed's work would probably fit where the Adele tracks come in. The beloved writer and podcaster is best known for her memoir Wild, which was made into a film and details her 1,000 mile hike across the Pacific Crest Trail after her mother's death.

But long before mainstream fame, Strayed already had a loyal following thanks to her weekly advice column for The Rumpus, Dear Sugar. Despite the fact that she wrote the colulmn anonymously, her unflinching honesty and radical empathy turned 'Sugar' into a cult phenomenon. In the words of writer and fellow podcaster Steve Almond, Strayed won her readers over by "laying herself bare, fearlessly, [so] that we might come to understand the nature of our own predicament".

Cheryl Strayed is in Melbourne this weekend for the Interrobang Festival. We caught up with her to ask about the art of advice-giving, why she calls herself a 'motherf—king feminist', and her new project with HBO.  

Daily Life: It's so exciting to have you in town. Have you been to Australia before?

Cheryl Strayed on the PCT hike she describes in 'Wild'.

Cheryl Strayed on the PCT hike she describes in 'Wild'.

Cheryl Strayed: I've been twice before. I love Australia, every time I fall in love with it and I think this is a country I can live in. I've been looking forward to coming back.


Your Dear Sugar column, which is now a podcast, has such a cult following. What does it feel like to be the world's agony aunt? Does it feel natural to you or did it take a while to get used to playing that role?

When I first started the column in The Rumpus in 2010, I had to figure out what my approach was going to be.  And then once I did, once I gave myself permission – I realised nothing ever qualifies anyone to give advice.

Cheryl Strayed with 'Wild' star and producer, actress Reese Witherspoon.

Cheryl Strayed with 'Wild' star and producer, actress Reese Witherspoon. Photo: Mark Davis

The only qualification to give advice is to be a human who is willing to think deeply about something and be as non-judgmental as possible. The reason most people don't give good advice is they can't separate their own judgement and opinion before telling us what we should do.

Is there one piece of advice that you always find helpful when something terrible happens?

The other day, I was in Austin, Texas and doing a talk for my new book [Brave Enough]. I was taking questions from the audience and one of the questions was from a woman, who was about my age. Her son was killed in a car accident earlier this year, he was 14. She was asking, essentially, "What do I do?"

The thing about grief always have a choice. So this terrible thing happened – you don't have control over that thing happening, but you do have the power over how you carry that forward in your life. You know, do you carry it forward in ways that are full of hate and destruction? Or do you carry it forward beautifully? And I've always been inspired by that.

So this is what I said to the woman who lost her son. I said, "This is awful. It will always be awful. You will suffer for your entire life. Until the day you die, you will suffer from his death. But you get to choose. You can bring the love you have for your son forward into your life and into the world in a way that gives to other people, consoles other people, or even something as simple as what I've done, which is to share the truth about my grief."

Sounds like the simple act of acknowledging that loss can be so powerful.

The interesting thing is, we equate healing and moving on, with 'letting go'. This is why I prefer using the phrase 'carry forward'. Carry into your life this suffering or this experience and make it beautiful.  That's different from just letting it go. We let go of the small heartbreaks – I'm not sad about any of the lovers I broke up with anymore, for instance, even though I was sad at the time.

But when you truly have suffered, your life is forever changed and it will always be part of you. In that sense, letting go is like a form of denial – it's a form of obliterating what has happened. Carrying it forward is a different thing, it's like saying this is always going to be a part of me, but I'm going to be able to make it.

Do you think having a physical journey, like the one you undertook in Wild, can help carry the pain forward?

For me, the physical aspect contributed greatly to my own healing. I was enacting, with my very own body, what I needed to do in my psychological life... Just putting one foot in front of the other even though it really hurts to do so, is exactly what living with grief is.    

I've read in a recent interview you called yourself a motherf--king feminist.  Have you always been passionate about feminism?

[Laughs] I've been a feminist all my life. I think I learned the word when I was maybe six or seven. For me, it's just as natural as the air I breathe. I was always a curious and intellectually engaged kid. And I quickly picked up on the world around me that there were all these conversations about...what girls should be like and what boys should be like. I just always found it to be utterly offensive and confounding. And I always battled against it.

Do you remember the first feminist author you read?

You know, when it comes to reading things that are overtly feminist, it would definitely be when I was in college. But when you first started asking that question, my mind immediately went to Judy Blume. I started reading her as a 9, 10, 11 year old and I don't know that I thought of her as a feminist as I was reading her. But [in retrospect] I think it's simply a radical act for her to write about the female body and female sexuality in a very honest way for young readers.

I learnt so much about sex and the body from Judy Blume. One of the things I thought about a lot as a young feminist was how little there was out there for me to feel okay about my body and my sexuality.  And I think Judy Blume is such a trailblazer in that regard.

Your book Tiny Beautiful Things (A collection of Strayed's Dear Sugar columns) is being made into an HBO series. How is that going?

My husband [Brian Lindstrom] and I are writing it together and executive producing. We have a development deal, which means we have to write the pilot and see what comes after that.

How do you plan to turn the advice columns into a screenplay?

Essentially the show will be about a character who is a lot like me but who isn't me: a writer who lives in Portland and is married and has a couple of kids. It's about her life and her marriage and their friendships. It's about people in their 30s, 40s, 50s in modern times. And this woman at the centre of it writes an anonymous advice column called Dear Sugar, just like I did. And so often the questions that she's considering and writing and addressing will echo what's happening in the lives of the characters in the show.

Will you star in it?

No! I'm not an actress. I'm a writer, and I'm going to stay a writer. [Laughs] Oh my god, it would be funny if I starred in it. Maybe I'll make a cameo, I'll be the maid or something.


Cheryl Strayed  will appear alongside Meghan Daum at The Interrobang: A Festival of Questions at 3:45 pm on the 28th of November.​