Tiffanie DeBartolo has followed many artistic pursuits throughout her life: she is the founder of the independent record label Bright Antenna, cofounder of the ShineMaker Foundation, a filmmaker, and the author of three novels.

Her most recent book, Sorrow, follows musician Joe Harper, a man quite unlike Tiffanie in that his life has been a series of intentionally-missed opportunities, artistic and otherwise. Tiffanie spoke to me about Sorrow, the inspiration behind it, and what it takes to write from a truly empathetic perspective.

(Warning: spoilers for Sorrow to follow!)

Kelli: So I guess the first question I want to ask you is probably something that a lot of people have asked you, which is: where did the idea for Sorrow come from?

Tiffanie: So originally, the idea came from a song by my third favorite band of all time, The National.

Kelli: Wait, what are your first two favorite bands? 

Tiffanie: U2 and Pearl Jam! 

So, The National has a song called “Pink Rabbits.” And it's a song that I had listened to hundreds and hundreds of times. It's just one of my favorite songs. But one day I was out on a hike and it came on, and there's a line in the song where he sings, “Somebody said you disappeared in a crowd; I didn't understand then, I don't understand now.” Something about that line really hit me and conjured up this whole scene of these two characters at an outdoor concert venue, and one of them just sort of ups and walks away. I was so curious about that scene, and why he left, and I went home and I started writing what would become Sorrow. And that scene, as you know, it comes much later in the book—but it was the first scene that I started writing. 

So that's kind of where it started. And of course, there are a lot of other factors that bleed into stories when you're writing them. But that was really the birth of the book.

Kelli: That's so interesting. So when you write, do you usually have your stories come to you in moments like that, like a scene that pops into your head? Or is this the first time that's happened to you?

Tiffanie: You know, it usually comes to me in the form of a feeling, I would say, and then the feeling kind of turns into a scene. Normally when I write—I mean, for my first two novels, I had a very strong sense of how the books were going to begin and how they were going to end. I knew the endings of both of those two books when I started them, and I just had to sort of get from A to Z. With Sorrow, I didn't know anything. I just had a feeling, and the characters grew out of these feelings that I was having, and the story took off from there. It was actually a pretty magical experience writing it, because there were certain scenes that I never saw coming until Joe saw them coming.

Kelli: Speaking of Joe: I think what impressed me the most about the novel was how deep all of your characters are, even the minor characters like Rae or Bob. We don't even meet Bob, but we know him, you know? I'm wondering if any of them are based on people you know, and if not, how do you go about creating characters that are fully formed and true to life?

Tiffanie: I think that subconsciously, I steal personality traits and characteristics from people that I know, but none of them in this book were intentional — put it that way. Even when I have in the past based characters on real people, the characters take on a life of their own. It's fun to kind of take something that you find quirky or interesting about someone and start a character with that. But once you get into the flow of writing, at least for me, those characters become very unique individuals that bear little resemblance to where they started.

Kelli: That makes sense. I'm especially interested in October. I think that her skills as an empath are really interesting. And like, almost supernatural. I liked how you explored how that lends itself to being an artist. When you conceived of her, did you come up with the artist part of her identity first, or the empathy part? 

Tiffanie: She was an artist before she had the mirror touch synesthesia condition. I remember like, really kind of struggling to figure her out. I was just having feelings about who she was, but hadn't really narrowed her personality down enough that I felt like I was writing truthfully about her. And then I randomly came across an article about mirror touch synesthesia, and I started researching it, and I was like, “Oh, this is who she is. This is really going to add a lot to the depth of their relationship and who she is.”

Kelli: I didn't even realize this condition existed, although I do have a couple of people in my life who are extremely empathetic and kind of have that reaction, where they get really emotional because of how other people feel.

Tiffanie: Yeah. And I feel like I do have that, in a much less dramatic way than she does, so that was why it was also kind of interesting for me to play with. Because as I was writing her, I was realizing how often in my life I had been energy-sucked by people who were just not feeling good, or just kind of taking on the pain of other people.

Kelli: Yeah, wow. I'm always like, I don't feel that way. And then I'm like, am I a psychopath?

Tiffanie: I think it's rare, honestly! And it can be a burden. You know, like Joe says, “How could that possibly be a gift?” Especially if you don't know what's happening because you assume they’re your own feelings. It took me a really long time to realize that sometimes when I was feeling heavy or full of sorrow, it wasn't my own. 

Kelli: Right. And in the book, October takes on a lot of Joe's pain and his trauma, especially when they have that conversation about it. Joe is a character with a lot of trauma, between his brother’s death and his strained relationship with his dad. How do you approach writing about trauma and the way it impacts a person's ability to function in the world?

Tiffanie: I have a lot of friends who have experienced some pretty deep and traumatic events in their lives, and I've known them long enough to witness how they behave and how they're triggered. I think that what I liked the most about doing that, and exploring that through Joe, was that it gave me an extra layer of empathy for where people are coming from sometimes when their behavior is hurtful or damaging to a relationship. To kind of learn how to step back and say, “Okay, this isn't about me, this is about something that happened to you 20 years ago, and I'm just bearing the brunt of it.”

Kelli: How did you go about writing Joe without making him... completely insufferable? 

Tiffanie: He is insufferable, sometimes!

Kelli: He is! But I guess because you're approaching his story from a place of empathy, the reader always comes back around to sympathizing with him. 

Tiffanie: Writing in first person made all the difference for that. Because if I had tried to write from an omniscient point of view, where I was just observing him—or even more difficult, if I were to write from one of the other characters’ points of view—I don't think that the reader would have A) understood him, or B) liked him, because we wouldn't have known what he was really and truly feeling. And I think that's the key to having him be a sympathetic character that people might like and/or relate to: we are standing in his shoes, and we can feel what he feels, and we can understand why he's reacting the way he is. Hopefully, in most cases, I think people can relate to him more than not.

Kelli: For sure. So, to go back to what you were talking about earlier with the scene at the concert: I thought it was really interesting how the story was structured. Because you have that framing device, where from the start we know that Joe is gonna hit rock bottom at some point, and then we go back and figure out how it happens. The whole time we're leading up to the part where the bad thing happens, and we know it's coming, and Joe even keeps saying “this is about to happen”—but there are still so many revelations and little surprises along the way. How did you decide on that sort of structure? And how did you know when to reveal certain things?

Tiffanie: That was another sort of magical process for me, where I remember starting that scene once I got to it again in the story, and being like, how is Cal gonna find out about Joe and October? And they were on stage, and I realized that Joe didn't have his shoes on. So it wasn't something that I planned or structured at all, it was just the evolution of the story. It felt right, that it would happen when they were having this moment that was so important to both of them and to their friendship. 

Kelli: Yeah, this was so much different than a lot of love triangles that I read about or see, because a lot of times you're on one person’s team or the other... and in this, it's really hard to be on either side, because it does happen by accident, and everyone is a good person. So I found that really interesting, too, because it's a lot more complicated. And I think that situations like this are often a lot more complicated than people realize. 

Tiffanie: I think that's the perfect word to describe it. It really is a very complicated situation. It's something that I strive for in my writing, to make all the characters as human as possible, and as dimensional as possible. So that was important to me, even when I was crafting Cal, because I didn't want people to be like, well just write that guy off.

Kelli:  Yeah, it was hard to even want them to break up, because I wanted him to be happy too. But it does make sense, because the way that he and October live their lives is very different. It's that thing where two people fall in love, but then they realize that it's not sustainable for them to stay together.

Tiffanie: I think that was something that that October realized, that she may have been attracted to him because he was so much that she wasn't. She thought maybe he would bring those traits out in her, but really, I think it just made her realize even more that she wasn't an extrovert like him.

Kelli: I've been in that exact situation, where I'm the introverted one. I'm always drawn to extroverted people in relationships, and then I often find myself like, being annoyed by them? And then I'm like, “I chose this because of that, so why am I now reacting badly to it?”

Tiffanie: That's exactly what she was going through. Like, no, I don't want you to have a party today.

Kelli: Yeah, I related to that a lot. 

On the blog, and the podcast, something that we talk a lot about when it comes to books about artists is whether or not the artwork we're reading about—whether it's visual art, or music, or whatever—feels authentic. How did you approach writing about making art and playing music in a way that felt real?

Tiffanie: Well, my other job in life is running an independent record label. I work with a lot of musicians, and I luckily turn to them a lot when I have music questions. Just spending a lot of time with them, you kind of get to know how they tick, so that was really helpful to me. As far as art goes, I had to do a lot of research, because I didn't know a lot about how the art world worked: how people actually made money in art, that kind of thing. But for the art exhibits themselves, those were just things that I've thought about doing in my life, but have absolutely no time to do. The selfie project is something that I came up with years ago, but of course I never got around to doing in real life. So I was like, let me just give it to her!

Kelli: I really enjoyed reading about all of that, because I'm an artist, and I like seeing the way that different people interpret what that means and how it feels, and what the purpose of art is. I really liked October’s philosophy, that every moment should be art, and to approach life as if everything you do is an act you are performing with thought and intention.

Tiffanie: I think that's a really beautiful way to live in the moment, looking at everything as some kind of ceremony to nourish your soul. Just to find beauty in things that you otherwise would either not notice or kind of judge “less than beautiful.” It definitely feels good inside to look at the world that way. It's just not easy to do all the time.

Kelli: It really stuck out to me a lot in that moment towards the end, when Sid is washing the dishes. It’s a private little moment of ritual that is comforting and calming for him, and it’s interesting to think about how something as maligned as washing the dishes can be art.

Tiffanie: Yeah. There are so many things in life that I feel like you can approach that way to make them more special.

Kelli: So this is maybe a boring question, but it's something that we talk about a lot on the podcast. If you were to slot your book into a genre, what would it be?

Tiffanie: I mean, that's a good question. It's funny, because a lot of people who love romance novels throw me into the romance category, and it kind of drives me crazy, because I don't see myself as a romance writer. Mainly because when I read romance novels, I look at that as fantasy, you know?  They're these idealized, dramatic relationship stories. And I try really hard to write about real people, real humans who are just struggling to figure out how to get along in the world, and how to love as best they can in the world. So, having said that, I would say that general literary fiction is probably the only place I can put myself.

Kelli: That makes sense. I think romance is a really interesting category. When you originally hear the word romance, or when we think of the romance genre, we think of erotica, or that fantastical kind of love you’re talking about. But lately, I've read a couple of books that were in that romance category but felt more real, like they had more depth, and I think it's great that the genre is making room for some deeper stories. But I totally see where it's frustrating, and part of it is probably being a woman writer and immediately getting put into a category because you're a woman and there's a love story in your book.

Tiffanie: Yeah, you hit the nail on the head. That's the frustrating part. I feel like if I wrote the exact same books, but I was a man, nobody would say these are romance novels. 

Kelli: For sure. So, for my final question: what future do you see for Joe after the book ends?

Tiffanie: You know, I feel like he definitely played on Cal’s album. He probably pursued music as a studio musician, probably records a lot with Cal, and they work together on songs. I have this image of him building he and October a house somewhere in West Marin, some big property where they could just make art and music and never have to leave, and have chickens and cows… That's my fantasy for how their life evolves after the book.

Kelli: That sounds perfect. I'm rooting for these fictional characters!

Tiffanie: Me too. 

Kelli: Okay, so tell me about your dogs.

Tiffanie: Okay, my dogs are so awesome. They are Irish Wolfhounds, so they're ginormous. One of them is seven feet tall on his hind legs, 180 pounds. And then they're super cute. They're very handsome boys. The gray one is named Dipsea, which is a trail near our house here, and the blonde one is named Kazoo. They are really incredible. Once when I was walking one down the street, a little girl asked me if he was a woolly mammoth. Sometimes my husband and I will be sitting on the couch and our dogs will walk by and we'll just be like, we live with furry dinosaurs. It's amazing. 

Kelli: Every time I see a very large dog, I'm just blown away. Dogs are so gentle. I have cats, and if my cat was that size, I would be dead.

Tiffanie: Yeah, they're so sweet and gentle, but they don't know their own weight. They sit on my lap and my legs are covered in bruises because of it.

Thanks so much to Tiffanie DeBartolo for joining me for this conversation! Sorrow is available now from Woodhall Press. You can learn more about Tiffanie at her website, TiffanieDeBartolo.com.