What Would Sugar Do?

On Tiny Beautiful Things and the wisdom of age

I’m uncomfortable thinking about the advice I would give my twenty-something self if I could talk to her. Something about it paralyzes me. But lately I can’t stop wanting to, in part because I recently experienced Tiny Beautiful Things by Cheryl Strayed in both book and Hulu series form. Next week I’m speaking at a virtual conference where she is the keynote speaker, and I like to be prepared for class. Also because my eldest child is graduating high school in a few weeks, and twenty years ago this month I graduated from college and moved to South Carolina. I feel mostly at peace with these sorts of milestones and the shocking realization that I’m old enough to have a child graduating high school. After all, I’ve had all this time to prepare. But Ms. Strayed has pushed my thoughts in uncomfortable places nonetheless.

I’m a big fan of hers, I should say. I chose Wild for my book club when it came out years ago, and I remember wishing I’d had the wherewithal to do a big hike like that when I was in my twenties. Granted, Strayed hiked in grief and emotional crisis. I wanted to go because I wanted to be the kind of person who’d done a big hike. I wanted the experience. I wanted to have something like that to write about. Any dreams for doing so were reluctantly shelved because I decided to have a baby instead. Reading about someone else’s experience brought up some regret for never having done it, and it made me wonder if I still could find myself on some lonely trail in the middle of nowhere.

The only thing I remember about our book club discussion was a dear friend’s reaction to the book and Strayed’s adventure, which I will paraphrase thus: She was so stupid! Hiking alone in the wilderness is a terrible idea! Why would anyone do this? No way, no thank you!

I laughed because this was the exact opposite of what I’d thought reading the book, and because my friend was kind of right. At least as far as my thirty-something self was concerned. I’d more or less found myself by then—not in the wilderness, but in a minivan driving kids to school. And although reading about hiking the Pacific Crest Trail made me wish I’d done something like that myself, I no longer really felt the need to do it. But I’m telling you this, reader, because I think it reveals something about youthful ideas. Or at least it reveals something about mine.

Although I had read several of the pieces in Tiny Beautiful Things over the years, I hadn’t read them all together until now. They are a collection of her Dear Sugar columns, which she started writing anonymously for the online journal The Rumpus before her Wild fame. Now she writes it on Substack. The show seems to be loosely based on Strayed’s life, weaving the transformational experience of writing it with the columns in clever ways. It features many of Strayed’s wise words and the fabulous Katheryn Hahn, who stole my heart in Stepbrothers and has kept me captivated with her work ever since. The book was recently reissued for the new show, and it includes several new columns that weren’t part of the original that were very lovely. The nature of the advice column, the anonymity, allows people to share their deepest troubles. It airs the dirtiest laundry, reveals the quandaries, and shows how silly and similar we all are. How off the rails it can all go. One doesn’t have to look far to see just how hard and shitty life can be, and Strayed’s well of empathy and sensitive insight are powerful enough to lead us home. Reading it—and the show too, though not as much—is the kind of experience that takes me apart and puts me back together again, like the Elton John song, “I’m Still Standing.” I became verklempt on like page three, and the feeling didn’t leave me until long after I’d finished.

One of Strayed’s classics is the title piece, “Tiny Beautiful Things,” in which she warns her twenty-something self of coming dangers and thought traps. Her twenties were, it sounds like from her writing, her wild years, whereas my twenties were more about settling in to the life I am currently living. I made all my biggest and most lasting decisions—to be a mom, to hitch myself to my kids’ father, to buy a house, to write. My wildest oats had already been sewn in college. But it was also really hard. In my twenties, I was ambitious, anxious, naive, and frustrated, and I’d often had too much to drink. I’d moved far away from all my friends to a place where it was really hard to make new ones. As haphazard as those years were for me though, it’s not like, as a mom and wife and person I am today, I can say I have any regrets about those big decisions. I also can’t say they didn’t come without sacrifices.

In the book, Strayed describes the choices not taken as sister lives of all the things we could have done instead. She writes, “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.”

In my twenties, I may have given up my freedom to through hike a long trail and any number of things. But a lot of that person’s dreams weren’t exactly well-informed. And some of them aren’t even that important anymore. Ah, the thrill of knowing better!

So what would I say to myself if I could go back?

We all get choices, and I suppose I would tell my twenty-something self to be more aware of the fact that we can’t have it all. Our choices may not seem life-altering at the time. But they might be. And they will all add up to the person you become, a life that you have to live with.

Don’t be so arrogant. Success isn’t an arrow that sails smoothly to a target. The target will move. The target will run in a zigzag pattern. The target will be switched out and change completely. And know that when you flippantly say, “If I can’t make money as a writer, I can always go back to waiting tables,” you might actually have to do it.

Although you’ll still be learning this very thing in twenty years, don’t be so hard on yourself. Not for the little things, and not for the big things either. Some lessons we have to learn the hard way. It’s okay not to know what you’re doing and to have to figure it out.

You can only be the person you are. You can only be the writer you are. Comparing yourself to others is an errand in misery. All the people who tell you this same thing are not kidding.

You do have something to say. You just might not be ready or willing to say it. And sometimes not saying it is okay too.

Don’t be so hard on other people. Life is as terrible as it is beautiful. We’re all struggling. And it feels much better to meet people with generosity of spirit, even when they’re behaving at their worst. Of course, this doesn’t mean you have to take anyone’s shit.

Your timelines are arbitrary and not everything will happen the way you plan for it to. No, honey, your first book will not be published to great acclaim by the time you’re thirty.

There’s no rush. But time will shock you with how fast it will fly by. Make sure you spend time every day doing something you love.

I would definitely tell myself not to drink so much. The memories are more memorable when you count your drinks.

And when you and your boyfriend are standing by an adorable baby in the grocery store checkout line, and he turns to you and smiles in a longing way, know that he’s serious.

Much of this wisdom came from experience. A lot of it also solidified for me by reading Cheryl Strayed’s essays. Some of them I’ve had to read a few times, and I will tuck Tiny Beautiful Things safely on my shelf for when I need to read them again. Now that I’ve thought it all through, I guess my discomfort about giving my younger self advice comes from the fact that, knowing me, I probably wouldn’t have listened.