Creative Chutzpah: How Modernizing the Dark Night of the Soul Led to Publishing Success

Photo by Prateek Gautam on Unsplash

This is a condensed conversation from our Zenith Salon, offered to members of Zenith virtual coworking, the space for authors, writers, artists, and creators to make dedicated time for the work that matters to them. To learn more about events like this, go to Zenithcowork.com.

Since this is a long read, feel free to use the headers to anchor your reading experience and scroll to the topics that interest you most.

---

On Creative Percolation and Chutzpah

Sara: I'd love to introduce you to Kelly Street—a dear friend, a therapist in private practice at Embrace the Dark & Alive Therapy, and the founder of Happy Rebel, which offers healing practices and products. She's also the host of The Happy Rebel podcast and the author of Embrace the Dark, a forthcoming book to be published by Llewellyn in 2026.

Kelly, I'd love to start with the book itself. What is the book about, and how did the idea first come to you?

Kelly: The working title is Embrace the Dark. It's really an exploration of how people experience the dark night of the soul across different areas of life—not just in the spiritual realm, which is where most people tend to place it.

As for how the idea came to me—it actually ties right into that theme. I think it was back in 2019 when I first came across Thomas Moore's book Dark Nights of the Soul. I first heard about it on a podcast, and I remember thinking, Damn, that sounds like something I need to read.

About six months later, I was in Chicago for work and we were moving offices. I was unpacking a box of books for the office bookshelf, and there it was. I asked my boss about it, and he told me it was an old book of his mom's that he'd brought into the office because it didn't really resonate with him. He said I could have it if I wanted it. So I took it home, and I read it twice in a row.

Over the next three years, that book stayed with me. The ideas in it kept percolating in my soul. And it wasn't that what Thomas Moore wrote wasn't enough—it absolutely was—but I felt like I had a different take. Something fresh. Something more modern. I wanted to explore what it might look like to approach these themes through the lens of a modern millennial woman—and see what emerged.

Sara: That's beautiful. What I really love about it is that it takes a certain kind of chutzpah to read Thomas Moore and think, I can put a fresh spin on this. That's bold.

So can you speak to that confidence? What allowed you to say, I see the holes, and I'm going to fill them?

Kelly: It's funny—hearing you say that, I'm like, Wait, do I actually have that confidence? I don't know that I feel like I do. But I guess I must, because I'm doing it.

In the six months to a year leading up to actually starting the writing process, I did a lot of journaling. I've always been a journaler, and I've known for most of my life that I'd write a book someday—but of course, to write a book, you actually have to write a book.

So around 2021 or 2022, I got together with a couple of girlfriends, and we started working through The Artist's Way by Julia Cameron. After we finished those 12 weeks, I just kept going. I kept journaling every morning, asking myself: What do I want to write about? Why?

And I kept returning to Dark Nights of the Soul. As I re-read it, I started noticing what felt like gaps—not in the sense that Moore did something wrong, but in the way the material was framed. I began to see how it could be reframed or expanded in a way that might speak to people who wouldn't otherwise connect with it.

At the same time, I just kept thinking: Everyone needs to know what a dark night of the soul is. That the depression you're experiencing might not be clinical—it could be a soul-level shift, a spiritual reckoning. It really felt like there was a cultural remembering that needed to happen. And I wanted to be part of that.

Sara: I want to go back to something you mentioned—did you say that after you first read the book, it kind of percolated for about three years before you started writing anything around your own take on it?

Kelly: Yeah—about three years. I read the book, and then life just kind of happened. In 2020, we moved about 45 minutes away to my husband's hometown. COVID hit, and I was starting grad school, so there were all these big life changes unfolding. And looking back, those shifts were part of the writing process too—even if I wasn't putting words on the page yet.

So no, it wasn't like I read the book and immediately had an aha moment. It was more of a slow burn—something that lived in the background and kept coming back to me until I was ready to start exploring it more intentionally.

Sara: That really speaks to the idea of percolation. Sometimes an idea needs time. You let it live with you. It didn't fizzle out—it stayed with you until you were ready to give it form.

Writing the Book Before the Book

Sara: When you're writing about a topic like this, the writing itself often takes you on a journey. You don't just write about the thing; you live it, or revisit it in some new way. Have you had that experience with this book?

Kelly: Yes, absolutely—100%. The writing process has definitely taken me on a journey. I started outlining in early 2022, and from the beginning, I found myself referencing a lot of different books.

Since your book wasn’t out yet (Writing on Purpose), I followed every step in Book in a Box by Tucker Max—did the exercises, wrote the outline—and by the time I finished, I already had something like 80 pages of material. And that was before I'd really dug into or expanded on any of the actual stories.

That was around March of 2022. At that point, I had a three-week window between finishing my coursework for my master's program and starting my internship. And in those three weeks, I wrote the entire first draft of the book.

Then I promptly put it aside for a full year, because I just didn't have the time or energy to keep working on it. When I finally came back to it, I gave myself about a week to re-read the draft and start going through it again. I hired editors, started refining it—and, yeah, that's kind of been the arc of the writing process so far.

As I was writing, I was revisiting all these personal stories—moments in my life where I'd experienced what I would now define as a dark night of the soul. And in writing them, I was re-experiencing those moments. But this time, I was moving through them differently—gaining new insights, new layers of understanding.

Sara: Yeah, it's interesting—because I think anyone can experience this kind of journey with whatever topic they're writing about. But your topic is especially deep, and potentially heavy. In a way, it's like you're saying, Let me be the carrier of this message, and in doing so, you have to really know it—deeply and personally.

That said, you mentioned taking about a year-long break—what did that time away from the manuscript do for you creatively?

Kelly: It definitely helped me come back to the manuscript with fresh eyes—and with a little more distance from how I'd written things.

I was okay with each break because I knew I needed the time, and I just didn't have the space for the book during that season. But when I came back to it with fresh eyes, something clicked. I'd heard this idea somewhere—that you write the book before the book. And that framing was really helpful for me.

Because when I re-read that first draft, it was clear: it was very memoir-heavy. And I realized that was the book before the book. I needed to write that version in order to find myself. But it wasn't the book that would help other people find themselves in the material. It was for me, but it wasn't quite ready to be for others yet.

Sara: That's such a good point—especially when a book is memoir-heavy. There's often a version that has to be written just for you. That draft is essential. It's the groundwork.

But if the book is meant to help others, there's usually another version that needs to emerge—not necessarily a full rewrite, but definitely a deep revision. One that reshapes the personal story so it actually becomes useful or meaningful for the reader.

Choosing a Publishing Path

Sara: Okay—so let's shift gears a bit and talk about your publishing path. When it came to this book, how did you think about getting it out into the world?

Kelly: So at first, I thought I could just manifest my way into the exact publishing deal I wanted. In the beginning, I told myself, Well, maybe I'll self-publish, but secretly, what I really wanted was to win the Hay House author contest.

So I went all in. I wrote a great proposal with help from another book editor, polished it up, submitted it… and two months later, I got nothing. No prize, no honorable mention, nothing.

So it was back to the drawing board. For the next six months, I sent the book out to every publisher and agent I could—probably 20 or 30 submissions total. And I heard nothing back. But even through that, I kept thinking, I can always self-publish. I was writing this book because I needed to get it into the world.

I gave myself until the end of 2024 to either land a publisher or move forward with self-publishing in 2025. Then, in September 2024, I got an email from Llewellyn saying they were interested. And exactly a month later, I was at a darkness retreat—very on-brand for me—about to enter several days alone in a pitch-black hut. Literally right before I went in, I got the email: they were giving me the green light.

Sara: So let's talk about that—because a lot of authors start to falter when they face rejection. But I didn't really hear you falter around the idea itself. What helped you keep moving through that?

Kelly: The radio silence was definitely the hardest part. I looked back at my emails recently and realized I sent the proposal to Llewellyn in the first week of January 2024—and I didn't hear back for almost ten months. When you're in it, with no updates, no responses, no feedback—it's hard.

But through all of that, I just knew. I knew this was the book I was supposed to write—the first book that needed to come through me. And I knew it was meant to be out in the world.

I wanted feedback. I wanted that external perspective. But the one thing I wasn't open to changing was the heart of it—the title, and my framing of the dark night of the soul. That part felt sacred. That part was non-negotiable.

Sara: What I'm hearing is that you also got really clear on what you weren't willing to compromise on. That's important. For people who may not know, when you work with a traditional publisher, even after you submit a full manuscript, they can come back and say something like, "We like the concept, but we want you to rewrite it with a different angle."

But what you're saying is, I've done the work. I know what I want to say. And I know how I want to say it. You had clarity on the framework, and you stood by that. That's huge.

Kelly: Yes—and I really went back and forth during that time. I had to ask myself, Is this actually the right fit? What kind of control am I giving up? And what do I need to hold onto for myself?

There's a delicate balance, I think, between stubbornness and certainty. And in this case, I was closer to certainty than stubbornness. I wasn't digging in just to dig in—I just really knew what I needed to protect, and what I was willing to be flexible on.

On the Vulnerability of Being Seen (Read)

Audience member: I'm curious: outside of having to re-experience so much of the depth and the dark night of the soul for yourself, what would you say was the most difficult part of your writing process?

Kelly: For me, the hardest part was definitely letting other people read what I'd written. That was unbelievably scary.

I took a few writing classes in college, but in those classes, the feedback process wasn't handled well. And I'm a sensitive soul. So the idea of handing over a piece of writing—especially something personal, based on real experiences in my life—and having someone critique it? That felt impossible.

But every time I did it, it got a little easier. Bit by bit, I started to build confidence. I started to think, Okay, maybe this is good. Maybe it's not perfect, but it's true. It represents me.

So yeah—sharing my work, letting it be seen and responded to—that was by far the hardest part.

Sara: It's such an interesting combination—because it's not just about being seen in your story, it's also about your creative output being seen. It's both: the personal vulnerability of the story and the artistic expression of it. And they're all wrapped up together, which makes it feel incredibly raw.

Kelly: And honestly—even now—it's still hard. Like, my husband hasn't read the whole book either. He read maybe the first 20 pages or so, and because he's got this very logical, entrepreneurial mind, he immediately jumped into feedback mode.

And I was just like—Nope. Too tender. Can't do it. Please stop reading. And he was like, "Okay, I get it. I'll read the final copy—when it's no longer up to me to edit it."

Sara: Totally—and that's such a great point. Choosing the right early reader is so important. And honestly, it's so often not your family. It takes a really specific kind of reader to offer helpful feedback without accidentally stepping on something tender.

Kelly: And to that end, I'll also say—I don't even know if my husband is the audience for this book. I mean, there's some crossover, sure—but he's probably not the reader I'm writing for. And that makes a difference, too.

Sara: That's one of the main challenges, right? A family member isn't just too close to you emotionally—they're also usually not your audience. They don't necessarily know who you're trying to reach or what you're trying to do with the work. So their feedback, even if it's well-meaning, can end up being confusing or misaligned.