Letter from a fellow optimist: Jessy Easton on digging for gold

"Every shadow moment I’ve lived through has also been an initiation."

Emma Vivian

and

Jessy Easton

Aug 24, 2025

Hi friend,

Welcome to Letter from a Fellow Optimist, where I hand the mic to another hopeful human.

This week, I am beyond humbled to welcome the wonderful

Jessy Easton

I first discovered Jessy through her bold mission to serialise her memoir, The One Who Leaves, right here on Substack. After hearing one too many agents say she needed a “platform” to earn a book deal, Jessy decided to take matters into her own hands. That choice has resonated deeply with fellow writers—Jessy’s Substack catapulted to bestseller status, and her words continue to resonate with thousands of readers.

Though it was Jessy’s fearless outlook which made me initially subscribe, it was her words that have kept me hooked ever since. It’s hard to describe the power Jessy’s writing has over me. Reading her emails feels like opening a letter from a friend. She writes the barebones truth, with equal parts tender and unflinching honesty. I’m always thrilled to see her name pop into my overcrowded inbox—no easy feat in today’s attention-overload society.

Please join me in giving Jessy the warmest of welcomes! I hope you’ll love her letter as much as I do.

Dear fellow optimist,

I’m writing to you, but really, I’m writing to me, too. I’m a silver-linings person, and I’m guessing you are, too, or you probably wouldn’t be here in this beautiful space of real-life optimism Emma has created.

It’s funny, though, because my life has been fucking hard. I was the baby left alone in a crib with Coca-Cola in my bottle. The three-year-old who watched the cops raid our house and pull my mother from the bed beside me. The daughter of a woman who robbed more than 300 homes and spent much of my childhood in and out of prison. The daughter of a man who built a meth lab in the garage of our home. I grew up on eviction notices, absence, and longing.

Okay, maybe funny isn’t the right word.

And yet, I’ve never been able to call it a sob story. Every shadow moment I’ve lived through has also been an initiation. The darkness didn’t just shape me, it trained me to look for light, to catch glimmers in impossible places, to believe there’s a through-line even when everything feels broken. That’s the thing with optimists, we’re often born in the cracks. It’s not that we’re naïve (okay, maybe a little, or at least, I was), it’s just that survival required it. We learned to lean toward the sun.

And sometimes, other people notice that light before you do. My husband, back when he was just a boy I was falling for on a summer music tour, used to call me sunshine. We were dirty and sweaty, mosquito-bitten, sleeping on dirty buses, but goddamn, I was happy. Happy to be out of the Mojave where I was raised, happy to be working, to be part of something bigger than myself, happy to be useful, to be valued, happy to be falling in love with the most beautiful person I’d ever seen. When he finally learned about my past, he said, “I don’t get it. You’re always so happy.” And all I could say was, because I’ve always found good here. You just have to learn how to look for it.

For me, optimism isn’t about looking away. It’s about digging. Excavating. Peeling back the rubble until you find the thing that sustains you. And if you keep digging, you will find it. The glimmer, the spring, the thread that keeps you moving. It’s about walking straight into the shadow and asking, Where is the gold here? What is life trying to show me in this exact place? Every painful thing in my story has carried seeds of resilience, creativity, tenderness. Seeds that sprouted into what I share with others: writing through fear, writing into the hard things, letting words carve a way forward.

That’s the work I do now. I help people turn toward the places they’ve avoided, the stories they were too afraid to touch. And what always feels like a damn miracle is that when the words finally come, they don’t just tell the story. They change you. You walk away as someone new. Writing, for me, has always been a kind of survival. A way of choosing optimism, a radical act of refusing to let the darkness have the last word.

So if you’re in a season where the light feels dim, maybe optimism isn’t something you have to force. Maybe it’s as simple, as ordinary, as standing in the wreckage of your own life and whispering, there’s good here, too. Maybe it’s asking yourself the question, What seed is this darkness planting in me, even if I can’t see it yet?

Here with you,
Jessy

AFTER/WORDS by Jessy Easton | Jessy’s Fear-to-Flow Framework | Instagram

A Few Questions for Jessy

Is there a quote, belief, or perspective that’s helped you lately?

I’ve been thinking a lot about fear as I step through some old patterns of limiting beliefs that kept me small for most of my life. It’s terrifying to attempt something you’ve always believed you couldn’t do, whether that voice came from inside or from the echoes of others. For years, I let fear decide how I showed up, how I hid, how I shrank. Lately, instead of fighting fear, I’ve been inviting it in. Making friends with it. Saying, I see you. Hell, I’m even thanking it because I know what it’s really doing is trying to protect me, and I get that. But I’m done letting it run the show. These days, I’m choosing to make decisions from who I want to become, not from the wounds of my childhood.

There’s a quote from Steven Pressfield in The War of Art that’s been a touchstone for me... “Fear tells us what we have to do. Remember our rule of thumb: The more scared we are of a work or calling, the more sure we can be that we have to do it.”

That whole book is gold, but that line especially has been staying with me.

What’s one small, silly, or sacred thing that’s been cheering you up?

Because I’ve been doing this whole “stepping through fear” thing, my nervous system has felt more taxed than usual. One thing that’s been surprisingly grounding (and kind of silly) is blasting the music I loved as a kid and into my early twenties.

Lately, Alanis Morissette’s Jagged Little Pill has been on repeat. I crank it up in the living room, and my four-year-old and I thrash around together. It’s so freeing and shakes the static out of my body in a way that feels really, really good.