My late grandmother taught grade school in the early 1960s. She taught for a handful of years and gave it up when my mother and aunt were still young. Teaching was just . . . too much. Too heavy. Too messy. Too sad. She went on to enjoy a lighter career working for the IRS. Her customers there had problems, sure, but they were pretty much always the same. She found comfort in the predictability of the work.

Half a century after my grandmother laid down her chalk for the final time, I picked up an Expo marker. She and my then-teacher boyfriend (my former-teacher husband today) tried to warn me about the heaviness, the mess, the sadness, but I went on with gusto. I’d call my grandmother every so often to regale her with my tales of a tender-footed teacher. She’d offer inspiration, validation, or consolation, and never, ever an “I told you so.” (She was not an I-told-you-so kind of person.) Sometimes she’d share tales of her own. Here’s her most famous:

Early in her stint as a classroom teacher, my grandmother selected E.B. White’s Charlotte’s Web as a read-aloud for her second graders. As the novel was still somewhat new, she was as oblivious to its contents as her young charges, looking forward to each afternoon’s literary adventure just as much as they did.

Marcia Jorgensen was a brilliant woman and an experienced reader, yet she’d somehow missed White’s less-than-subtle foreshadowing throughout the novel. When the book was over and Charlotte’s final sacrificial silk had been spun, my very private grandmother was reduced to a puddle of very public tears in front of a roomful of 7-year-olds. How had she not seen it coming?

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This story is famous not solely for the spectacle involved in this embarrassing scene, but also for how it changed my grandmother’s reading life. She went on to consume probably thousands of books in her lifetime, but never again did she do it the customary way. No, from then on, my grandmother always read the last chapter of a book first. She was then spared the surprise of any potential plot twists or tragedies. My family and I teased her relentlessly about this habit, but she was steadfast. She needed to distance herself from the heaviness, the mess, the sadness.

A few weeks ago, my 5-year-old son brought a heavy blue book to me at bedtime: the E.B. White collection his own grandparents had given him for his first birthday. We’d already read Stuart Little, and it was time for the next story. My husband called then to say goodnight. (He gave up teaching two years ago for a lighter career as a firefighter/EMT). When I told him we were just starting Charlotte’s Web, he asked, “At the end, or at the beginning?”

Titus was puzzled at the foolishness of this question. He’s been educating his brother on the book etiquette he’s learning in kindergarten (where to find the author’s and illustrator’s names, how to safely store and care for books, how to turn pages without ripping them, etc.), but he’d felt it went without saying that you read a book from left to right, just like you read a word. I assured him this was correct, and we all said goodnight without any more talk on the matter. But I went to bed worrying over how to prepare my little boy for Charlotte’s inevitable demise.

Titus is very much his mother’s son, and she, her grandmother’s granddaughter. He has the ability to feel every little bit of the joy the world offers him with every little bit of himself, but can also be consumed, to the same intense degree, by its heaviness, its mess, its sadness. I have been known to steer him swiftly away from the heavier moments with creative revisions (“And just as the Titanic was starting to go down, the rescue boats arrived!”), but I know I can only rescue my budding reader so long before he finds out on his own that not every story has a happy ending.

Tonight, I prepared myself for the penultimate chapter of Charlotte’s Web, aptly titled “Last Day.” Charlotte’s plot to save Wilbur from the butcher has gone off just as she has hoped, but all the work she’s done on her web has overtaxed her, and she is on the last of her eight legs.

From his place on my chest, Titus squeaks “Of!” “The!” “She!”—pointing out sight words in a way that reveals he is not entirely engaged in the story. I decide I don’t want him to be blindsided, the way his great-grandmother was 60 years ago, so I give myself fully to the character, making my voice small and tired as I read Charlotte’s last monologue: “I feel peaceful. Your success in the ring this morning was, to a small degree, my success. Nothing can harm you now.”

Titus has stopped pointing out sight words or adjusting my hand on the corner of the page so I might turn it more gently. He is quiet and still. I continue reading: “After all, what’s a life, anyway? We’re born, we live a little while, we die.” I think of my grandmother, reading these words aloud for the first time, her eyes filling with tears, the way mine are as I read them now.

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“A spider’s life can’t help being something of a mess, with all the trapping and eating of flies.” I think of my grandmother, whose childhood was one of heaviness, mess, and sadness.

“By helping you, perhaps I was trying to lift up my life a little. Heaven knows anyone’s life can stand a little of that.” I think of my grandmother, who went on to seek the light that life had to offer her, living with as much purpose, clarity, and intention as Charlotte did.

“‘I will not be going back to the barn,’ she said.” I think of my grandmother, who accepted the expiration of her earthly body with grace and peace, knowing from the beginning how her story would end.

“‘Good-bye!’ she whispered. Then she summoned all her strength and waved one of her front legs at him. She never moved again.” I think of my grandmother looking down on us, enjoying this scene from Heaven, her epilogue. She watches her granddaughter blubber through the final paragraph of the chapter, considering that I might have softened this blow if I’d only read this part first. But she is not an I-told-you-so kind of person.

Titus is still, but he is no longer quiet. I feel his small body trembling before I hear it. He is snoring softly. I know that my children’s lives, like all our lives, will not be without heaviness, mess, or sadness, but I am grateful tonight for the gift of this timely slumber. Like my grandmother before me, I will seek to embrace the light life offers me and recognize it when I see it.

“These autumn days will shorten and grow cold. The leaves will shake loose from the trees and fall. Christmas will come, then the snows of winter. You will live to enjoy the beauty of the frozen world, for you mean a great deal to Zuckerman and he will not harm you, ever. Winter will pass, the days will lengthen, the ice will melt in the pasture pond. The song sparrow will return and sing, the frogs will awake, the warm wind will blow again. All these sights and sounds and smells will be yours to enjoy, Wilbur—this lovely world, these precious days…”