Long before her smash hit memoir Wild revived Oprah’s book club and spent 126 weeks on the New York Times best seller list, Cheryl Strayed ministered to the lost, lonely and heartsick in her advice column Dear Sugar.  Week after week, thousands wrote Sugar, Strayed’s darling pseudonym, with their dilemmas.  Should a vaguely dissatisfied young woman leave her boyfriend even though she loves him?  Should a middle-aged man finally exchange the glorious freedom of bachelorhood for a dull domestic life of pacifiers and cribs?  Should a soon-to-be bride invite her abusive, alcoholic father to her wedding out of a sense of familial obligation?  Should a man who’s weary of love after a bitter divorce, utter those irrevocable words “I love you” to his new girlfriend?

Strayed’s responses, complied in the altogether lovely collection Tiny Beautiful Things, are glimmering, gutting, gorgeous.  What’s most endearing about Sugar is her voice, which is at times gentle and compassionate; at others, tough and no-nonsense.  She’ll call her letter writers affectionate pet names like “sweet pea” and “honey bun” no matter how seemingly shameful their revelations.  But if you’re wallowing in self-pity or making excuses for your shit, she won’t have it.  No, you [obviously] shouldn’t have slept with your friend’s ex.  No, you shouldn’t feel sorry for yourself because— gasp— your parents regard you as an adult and expect you to pay off your student debt.  Sugar is a wise, warm-hearted, hilarious friend: she won’t shame you, but she’ll hold you accountable when you do something stupid.

I respect Strayed because she’s had her share of hardship.  She grew up poor in rural Minnesota in a house without indoor plumbing or electricity and lost her mother in her early twenties.  Unlike many advice columnists, Strayed doesn’t offer empty-headed platitudes or insincere “it’ll be okay’s”— she speaks with the hard-won wisdom of someone who’s known enormous loss and terrible heartbreak.

cheryl strayed

In the closing letter of Tiny Beautiful Things, a devoted reader who calls herself Seeking Wisdom writes Strayed with a “short and simple” question: what would you tell your twenty-something self if you could talk to her now?

Like Seeking Wisdom, many of us are tormented in our twenties.  Where are we going?  Did we chose the right career?  the right boyfriend/girlfriend?  the right city?  When would we “make it”?  Would we ever?  When— to put it simply— would we finally have our shit together?

Haunted by insecurity, we worry we’re falling further and further behind our more successful, more stable peers.  While they’re getting PhD’s from prestigious Ivy League universities and settling down and buying houses and having kids, we’re chasing the grand dream of becoming a writer (or some other equally difficult/poorly paid profession).  While they discuss grown up things like real estate investments and mortgage payments, we’re renting a cramped apartment and nowhere near financially secure enough to think about home ownership.  We write and write and write but still— after years— have yet to “make it” in a conventional sense: we have yet to write a book, we have yet to see our name on any best-seller list.  The only thing in our inbox are dispiriting rejection slips.

Maybe— we start to think— this whole writing thing isn’t worth it.  Maybe our grand dreams are  grandiose.  Maybe we should just give up.

Strayed tells us one thing: don’t Don’t measure yourself by the cruel yardstick of other people.  Don’t worry so much about “making it.”  Don’t conflate being a writer with being publishedWrite for its own sake— not external validation:

“Don’t lament so much about how your career is going to turn out.  You don’t have a career.  You have a life.  Do the work.  Keep the faith.  Be true blue.  You are a writer because you write.  Keep writing and quit your bitching.  Your book has a birthday.  You don’t know what it is yet.” 

In our accomplishment-crazed culture, we focus on product, not process.  Rather than cherish the remarkable process of becoming, we obsess about being.  Our biggest fear?  That we’ll spend years scribbling in our notebooks and not “accomplish” anything: not see our name in print, not land a six-figure book deal.  We glamorize the myth of the overnight success and begin to doubt our path when our dreams take too long to manifest.  Years, decades have passed…why haven’t we “made it”?  In moments like these, we must remember the wise words of Rainer Maria Rilke: “In this there is no measuring with time, a year doesn’t matter, and ten years are nothing.  Being an artist means: not numbering and counting, but ripening like a tree, which doesn’t force its sap, and stands confidently in the storms of spring.”

Strayed herself didn’t publish Wild until she was forty three.  Though she hated herself for not writing a book by the time she was thirty, as she got older, she realized her life had unfolded exactly as it was meant to.  “To get to the point I had to get to to write my first book, I had to do everything in my twenties,” she confesses in another soul-stretching letter, “I had to write a lot of sentences that never turned into anything and stories that never miraculously formed a novel.  I had to waste time and grieve my mother and come to terms with my childhood and have stupid and sweet and scandalous sexual relationships and grow.”

Though in our capitalistic, efficiency-obsessed society, we imagine there’s nothing worse than “wasting” time, Strayed argues nothing is a waste.  Keeping a diary, committing poems to memory, reading essay collections and 19th century Victorian novels and memoirs and biographies, spending idle afternoons daydreaming, wandering from city to city, loving someone for ten years only to have the relationship disintegrate: these are not detours— they’re part of our path to becoming the person we were meant to be.  Strayed concludes by asking Seeking Wisdom to trust in her life’s unfolding:

“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.”

Tiny Beautiful Things is consoling in its entirety.  Want more honest, heartfelt advice from Sugar?  Read Strayed on trusting your truest truth and having the courage to “go” and being brave enough to break your own heart.

3 thoughts on “Cheryl Strayed on Trusting the Unfathomable Beauty of Our Becoming

Leave a Reply to Maegan Cancel reply