7 Pieces of Life Changing Writing Advice From Dear Sugar
What happens when a mega-bestselling author spends two years writing an anonymous advice column about love, life, loss, pain, and work? Some of the best insights on the craft of writing and the writer’s journey that you’ll ever read, that’s what.
I’m talking about Cheryl Strayed, author of Wild, who since 2010 also happens to have sidelined as Dear Sugar on The Rumpus. Those columns, which have long been cult favorites on the internet, have recently been adapted into an amazing book. Most of them have nothing to do with writing. Most of the letter writers are just normal people struggling with life. Most of the time her answers stop being answers and become deeply moving essays that stand on their own. And occasionally, when we are lucky, those essays address what it means to be a writer and the struggle with having something to say.
I’ve broken out that advice below. I hope it resonates as much with you as it did with me.
1. Contain the Arrogance
In one letter, Strayed hears from a 26-year-old who is depressed that she has not yet found success as a writer. She cannot seem to write the big, transformative, feminist book she believes she is destined to write, and the people in her life have not been supportive and do not understand her drive. Sugar immediately zeroes in on the real problem: arrogance.
Beneath all the anxiety and sorrow and fear and self-loathing: there’s arrogance at its core. It presumes you should be a success at 26, when it really it takes most writers so much longer. It laments that you’ll never be as good as David Foster Wallace—a genius, a master of the craft—while at the same time describing how little you write. You loathe yourself and yet you’re consumed by the grandiose ideas you have about your own importance. You’re up too high and down too low. Neither is a place where we get any work done.
2. On Giving Up
Of course everyone feels like quitting sometimes. Everyone runs into trouble and problems and temptations. Sugar has great advice:
The thing about rising is we have to continue upward. The thing about going beyond is we have to keep going… Every last one of us can do better than give up.
3. Your Book Has A Birthday
A 22-year-old asks: What would Sugar tell her twenty-something self? Along with a bunch of other great advice, Sugar speaks to the fear and uncertainty young writers have about their careers:
Don’t lament so much about how your career is going to turn out. You don’t have a career. You have a life…You are a writer because you write. Keep writing and quit your bitching.
But then she concludes with something every creative type can take faith in remembering:
Your book has a birthday. You don’t know what it is yet.
4. Play The Cards You’re Dealt
A letter writer complains that her parents have cut her off and now graduate school appears out of reach. In this case, I’m not sure the person wants to be a writer, but Sugar replies with a story about a friend from college who she was deeply jealous of. This friend, Kate, had her college paid for, had a year abroad paid for, had a cushy internship at GQ, French lessons, and of course, a new car as a graduation present. Sugar, who desperately wanted to be a writer, was angry because she needed these experiences to fuel her work. Instead she was stuck grinding it out in low wage jobs and had lost both her parents. Why? How is that fair?
Here’s the long and short of it: There is no why. You don’t have a right to the cards you believe you should have been dealt. You have an obligation to play the hell out of the ones you’re holding. And, dear one, you and I both were granted a mighty generous hand.
The moral of course, is that Sugar’s jobs and experience ultimately did fuel her bestselling books. Which is how it works. Your life is what makes you a writer and gives you something to say.
5. There’s A Difference Between Books and Book Deals
A novelist with an MFA from a prestigious school asks how to handle the conflicting feelings of anger and guilt at the success of writers they believe they are more talented than. Sugar makes an important point that we can all remember:
We are not talking about books. We are talking about book deals. You know they are not the same thing, right? One is the art you create by writing like a motherfucker for a long time. The other is the thing the marketplace decides to do with your creation.
In other words, as writers what we control is the work—not its value on a somewhat arbitrary and unforgiving market. You cannot conflate the two or let financial success determine the “value” of your work. This is creative suicide. You can’t care about externals–only the effort you put in.
6. Humility & Surrender
In the same letter she writes to the grandiose aspiring writer, Sugar mentions a trick that helped with her first book. On a chalkboard in her living room she wrote a quote from Flannery O’Connor:
The first product of self-knowledge is humility.
And on the other side she wrote a quote from Eudora Welty that reminded her of the loss of her mother:
She sat and thought of only one thing, of her mother holding and holding onto their hands.
She recommends this to all young writers as follows:
If you had a two-sided chalkboard in your living room I’d write humility on one side and surrender on the other for you. That’s what I think you need to find and do to get yourself out of the funk you’re in.
We could all use a reminder of these traits.
7. Turning Pain into Pages and Progress
Someone writes in about a boyfriend who is very open about his sexual past but it makes the writer jealous and uncomfortable. Sugar replies with words to help improve communication in that relationship but that apply to every writer, no matter what they write and what they experience.
Let yourself be gutted. Let it open you. Start here.
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This probably sounds extreme, but I think Strayed’s advice here is worth more than the costs of any MFA program in money or time. Take it and apply it to your life and your work. It’s simple. Manage your ego. Live and do interesting things. Read voraciously. And of course, practice humility (and don’t worry about calling yourself a “writer”). By getting into this mindset, you can develop the resilience required for such an unforgiving profession and pass those that are stuck with issues you now realize don’t really matter. 
