Kaylee Daugherty: When Stars and Planets Align

Kaylee Daugherty. Photo by Cathryn Beeks.

On a warm winter morning, I was treated to a cup of coffee thoughtfully styled my way, and a comfy chair on a lovely vine-covered back patio, with butterfly visitors and the chimes of a church bell nearby. Sitting across from Kaylee Daugherty feels a bit like lounging alongside moving water. Sometimes she’s a slow-moving, pensive brook, other times she’s torrential, and you just never know when the tides will shift—but either way, it’s enjoyable. She draws you in and you want to listen. Her voice is melodically expressive, with quick starts and stops, and drops in volume, colored with giggles.

A fairly recent addition to the San Diego music scene, Daugherty has been gigging for five years but only started sharing her original music about a year ago. That was when she first came to the Writers Round San Diego open mic at the Ould Sod in Normal Heights. Like so many musicians, she has found a community there and it has been a driving force for her creatively. Not only that, but she is also fully connected to what others are doing as well. That’s part of the strength and allure of WRSD, you’re there for yourself but also for everyone else, and somehow by supporting others, you feel that push upward, that rising tide. She says, “It’s a place where I can share my stuff, hear other people’s stuff, and have people actually remember my songs and my lyrics. It’s, oh, so special.”

Although she’s looking forward to recording a full album in the future, 2024 saw the release of Glimmer, her three-song EP, recorded at San Diego Music and Arts Company. When presented with the opportunity to record it there, she almost declined because she didn’t feel “good enough.” Diving further into those sentiments, she explains, “I didn’t feel mature enough as a musician and as a songwriter. But I was, like, man, this is such a good opportunity, if I’m gonna ever record music, I have to start somewhere, you know? And so I was, like, let’s do it. And so that EP, I am proud of it. I do feel like I’ve grown from it and I’m excited to release music that is more reflective of where I am now.”

Completely green, Daugherty had been apprehensive about the whole studio process but found it to be less scary than she thought. She came in with ideas, but also, her recording engineer Kris Calabio had their own ideas to contribute as well. It turned out to be nothing like she expected. The process was collaborative and free, as she played multiple instruments and layered them with sounds. “We had so much fun,” she says. “And then on one of my songs, ‘The Morning,’ I’m fully doing stuff. So, I’m, like, sitting down with a cup of coffee and I’m stirring it. You hear sipping. I’m trying to illustrate the lyrics of the song, like, waking up with someone in the morning and all of the sounds of that, the birds chirping.”

About the process, she continues, “So I thought that I was gonna walk into it so uptight and nervous and aiming for perfection and not satisfied with anything less. But it ended up being so much fun and organic that it was, you know, one take and then, well, that’s what my voice sounds like, right? So, if I’m gonna be honest here, it’s not perfect, is it? No, but that is what it sounds like.” I certainly respect her frankness and willingness to accept herself as she is right now. How refreshing.

For the moment, Daugherty is happy with where she is. Someone recently told her, “You’re going to make it, I believe in you.” But what struck her instantly was the realization that she is already satisfied. She knows that success can look different for everyone and her view of what it means has evolved. In the beginning, she just wanted to gig regularly, to be engaged with people and the scene, and to gain acceptance as part of it, to feel included. But five years ago, at just 24, she already felt like a latecomer. Without knowing anyone in the business or having a formal music education, she believed she was at a disadvantage.

Having grown up in the church, music was a big part of the twice-weekly attendance, which meant that she was more involved in it than most of her peers. She was in choir as a young child, on the worship team at 11, and later became the worship director at a church in Oceanside. At that time, music was still something on the side, yet it was a passion. When searching for subs for her team, she tapped into the jazz program at Mira Costa, which became her entry point into the genre and to gigging with those musicians. This newfound direction led her on a path away from the church and to fulfillment.

She had begun to ask questions and was never satisfied with the usual responses of, “Well, you know, you can’t know everything because you’re not God.”

Up to that point in her life, everything she did was centered around the church and her purpose in all things was for the glory of God. Looking back on blog posts she wrote back then makes her realize how much she’s changed, and she finds it hard to even recognize that girl from just five years ago.

Of the separation, she says, “Oh, it’s such a huge transition. I didn’t think I would ever be able to do it, because it’s such an identity that you have to somehow remove from yourself. But, somehow, some way, I got through it. I lost a lot of friends, but I made a lot in this community, I’ve made so many friends. It’s the first time in my life I feel like I have a really good, strong community. So, I’m really happy.”

Her tenacity and willingness to welcome opportunities has allowed her to strip away some of those perceived disadvantages. Apart from her solo singer songwriter gigs, she is also a staple jazz singer and performs out with a multitude of other musicians. In addition to English, Daugherty sings equally well in Spanish, Portuguese, French, and Italian with confidence and ease; she is also fluent in the styles of swing, blues, and bossa nova. In discussing both sides of her career, she says, “Music is just such a joy. It was always a passion and something fun, but it’s really awesome that now it’s a career, something I can be proud of, especially my originals. I love playing my jazz standards and stuff, because people really can connect when they recognize music, and especially if it’s nostalgic and opens a portal to another time. But with my originals, it’s so fulfilling to play what’s in my heart. It’s like reading my diary to people and then seeing them relate to it is amazing. And then I see people touched by it, and it makes it worth it.”

As one who lives in the moment, Daugherty doesn’t have a lot of regrets. She can see mistakes she’s made, acknowledge them, and work to make better choices, but it doesn’t make her anxious; rather it keeps her looking forward. Sometimes she can get wrapped up in herself and become shortsighted, which ends up with day-to-day stuff, such as cleaning her house, simply not getting done. Eventually, it becomes a distraction. Yet, while attempting to remedy the situation, a song will occur to her, making her wonder why she started cleaning in the first place. Music is her ultimate distraction.

Daugherty strives to be friendly and inviting and to make people feel welcome and part of the community. But there have been times when she has pulled back from friends and stopped reaching out. Going through a bout of COVID and other life stresses played a big role in her isolation. She knows that friendships are important and that they need to be nurtured. She understands how she may have hurt some by not responding to messages, not coming around, just not connecting. Thankfully, there finally came a time, when it cleared, and she was back in touch and involved. This would be one thing she would want people to forget about her; instead, she hopes they remember that she cares about them, even when she’s down.

She has consistently worked hard to include herself out there in San Diego’s music scene in one capacity or another.

Kaylee at Dizzy’s for an Eydie Gormé tribute. Photo by Manual Cruces Camberos.

Bringing it up often during our interview, Daugherty expressed her admiration for Writers Round San Diego and all it stands for and seeks to promote. She is fortunate to have a family that supports her musical endeavors, but the sense of community there goes beyond that. She values how the group shares a collective passion, each artist expressing it in unique ways. She says, “They understand the struggles of being a musician and being so vulnerable with your music and wearing your heart on your sleeve in front of others, where you might be judged. And so, I feel like we really just love on each other. Man, if I did not have Writers Round, I would not be writing.”

She admits to having written just one song in 2018, two in 2019, nothing in 2020, and two in 2021. But because of the care from that group, she now has around 60 songs. “It’s amazing to have a community that actually listens and cares genuinely. It’s not just like, oh, nice to see you. It’s so different than any other open mics because at every other open mic, people are there, and they know they’re gonna get a spot. And so they go, they’re just sitting in their chair going, okay, I have to remember. C, F, G, A minor, and remember the bridge, and then they go up and they play their song, and then they go, peace, and then they leave. Because it’s really just about them. But at Writers Round, more than half the time, you’re not gonna get picked, and so if you’re there, you’re there because you wanna listen, learn, engage with the community, and it’s not about you. It’s about us, and I love that. That makes me feel very supported.”

Daugherty feels kinship and friendship with so many people there, who are in different stages of life, but who are all connected through music. She explains, “You’ll have a 22-year-old who just started writing and they’re learning their first chords. And then you’ll have someone like Mark Montijo who’s just been, you know, playing forever ever ever ever ever ever. And you’ll have a rapper. I love it. It’s so awesome. Because we hear each other’s songs that are literally our heart, then it’s like, not only are we friends, we know each other so deeply.”

Kaylee with Leon Bisquera, Gil Hansen, Steve Alaniz, Johnny Meza at Palm Springs Underground. Photo by Kurt Kaltschmidt.

She recently participated in a song swap show, in which she played the song “Lost Art” by Montijo, and he played one of hers. “Oh, my gosh. It was one of my favorite moments in my life, honestly.” She felt honored to have such a seasoned singer-songwriter interpret one of her songs, and in a way so differently than her own. “It was a really, really special song to me. It was about growing up, you know, leaving home and coming back and then seeing that things have changed, seeing your parents get older, your dog get older. So, man, it’s a hard song. But the way I play it is very upbeat and kinda tongue in cheek.” She continues, “But then the way he played it was so heartfelt and, so then I’m on stage just crying, and everyone’s crying. And, oh my gosh. It was so special.”

When I asked her what success looks like, she said, “Before, I was just trying to get momentum, then it turned into, ‘Can I make money from this and actually make it my full income?’ But now just being engaged in the community, I feel very successful, and it isn’t touring across the country or selling so many copies of an album or playing at the coolest venues in town. It’s just an integral part of my life.” Recognizing that she is pouring herself into the scene, she continues, “If I could do that for the rest of my life, the way that I am now, then I would die a happy woman.”

Giving to the community, making it grow, making it an accepting place for others to also grow, represents the almost noble part of who she is. “We all help each other out,” she says, then continues, “Lately, I’ve been getting together with some girls in the community to work on stuff, like songwriting, and that’s been really fulfilling to me. I’ve really enjoyed that a lot, because there are some people that maybe have melodies and lyrics in their head, but they’re not on an instrument yet, so then we’re sitting together and fleshing out their songs. And to see on their face their song fleshed out and actually come to life, that’s success. That feels so good. Because now, I’m bridging the gap between someone who maybe wouldn’t have ever actually finished a song. Now they finished their first song, and then a week later, they finished their second. It’s given me so much life, just giving back to them feels very, very, very good.”

Accepting that she really isn’t cut out for a typical 9-to-5 job, she is delighted that she gets to go to work and “fuck around.” She’s usually in charge of picking the music she’s playing and gets to hire her favorite people and play her favorite music. “Oh, I love that,” she says. But being a musician myself, I know there is a downside, and I want her to talk about what she doesn’t like.

“It’s hard to put yourself into a sellable box,” she says, “to feel like a product for sale, to try to convince people of the value, especially when you’re talking about gigs and venues, and you’re, like, ‘I am worth a $100 an hour.’ And they’re, like, ‘I think you’re worth $25 an hour.’”

Kaylee with Aaron Lind, Joe Amato at Lou Lou’s. Photo by Lilia Rose.

She relates that music isn’t like the typical job that you interview and negotiate for and then climb up the ladder; the industry is so unpredictable. “You’ll be playing Lou Lou’s one day, which is a fantastic jazz club, and the next day, you’ll be playing a coffee shop where there are three people. And so that’s how it is forever, you know, like, even when you’ve been on the scene for 30 years.” She finds that can be a bit discouraging. “I am having to cold email and call places sometimes. And, you know, when you send a hundred emails with who you are, your bio, and your demos, and then you get two or three responses, it’s just like, wow. This is demoralizing. So, you’re always paddling.”

Then there’s the social media aspect, “Having to always promote yourself, it feels very, like everybody look at me. Me me me me me me. And that’s an icky feeling, to just be like, hey, guys, look at how cool I am. You should come to my show instead of their show. I don’t like it.” I can certainly relate; I don’t like it either.

I share with her that I have not interviewed anyone who feels any different. I say, “It’s horrible that we make what we make out of love, and we have to cross that barrier and go to the other side.”

We agree that, as musicians, our creativity is a labor of love. She says, “People talk about analytics and trends and time of day that you post and the tags. Some people do it really well and I respect that, and I really take notes from them. But it’s so hard to be consistent. I’ll get on a good wave of being present and posting, but it never lasts because that’s not my passion. I hate Facebook.” And then she brings to light another aspect, “If I wasn’t a musician that had to advertise, I’d be way more removed from social media. It’s such a connector, but it can feel very phony. And I don’t wanna be phony. I wanna, you know, be the opposite. I wanna be real.”

Agreeing that talent alone and the love of doing it aren’t enough, I ask her what holds her back, what her fears are. She answers with all the typical limiting self talk: “I have it in my brain, that little voice that’s like, oh, you know, everyone else is way ahead of you. And how are you ever gonna catch up? How are you ever gonna, you know, measure up to them? So just forget about it.” Damn that little voice.

When singing, she knows she can hold her own, but now she’s trying to grow as a guitar player. She feels intimidated by more advanced players, and her lack of confidence can be crippling. She says, “The gap between me and them is wide, it’s hard to get the courage to even try.” Yet lately, although it’s up and down, she has begun to see some progress, and that gives her hope. She wants to be able to fully accompany herself, she says, “When you accompany yourself, you can really breathe with yourself and, you know, you have more ownership of your music and it just opens the world of gigging to you. I’ve been playing solo mostly lately, and it’s been hard.” Even as she says this to me, I know it doesn’t matter that it’s hard. In this short time, I’ve come to know that Kaylee Daugherty is a fireball of talent, pure and wholesome ambition, generosity, and driven to do her art the best she can. She won’t let “hard” get in the way.

She had the chance to perform her originals last September at the Music Box and, as she was booked months in advance, she had plenty of time to let her nerves run away with her all the way up until the night of the show. But once it came down to it, she realized she was ready. She shares, “You know, I was in my favorite outfit with my favorite people. And, you know, I wrote arrangements. Like, I was on Musescore actually writing physical arrangements of these scores. And everyone had such good ideas and took it places that I never would have thought. To be on stage with your favorite people, you know, favorite musicians musically, but also just people that you like, love, as soon as we started playing; I was having such a good time, and it went so well. It wasn’t perfect, but man, I had a good time. It was so fulfilling to hear my originals that literally start as a little voice in your head, like a phrase or a melody, and to see them fleshed out with drum set, violin, and upright bass.”

…if you’re focusing on happy, you’re gonna notice happy. If you’re focusing on bad, you’re gonna see the bad.

I’m beginning to see a pattern here of starts and stutters, but nothing truly holds Daugherty back, she keeps getting up and moving forward. Her intention is clear and whatever the mechanism, it will serve her, or she will leave it behind. She remains positive. I asked her how she stays that way. “I think that growing up an only child, my parents gave me undivided love, and I think that made me a happy and well-adjusted person. I think that there’s always something good, and it’s like the analogy that if you’re looking for red cars, you’re gonna find red cars. You know? So, if you’re focusing on happy, you’re gonna notice happy. If you’re focusing on bad, you’re gonna see the bad. And I don’t wanna stick my head in the sand and ignore all the awful things in the world. But if there’s something that I can affect, I will take the time to focus on it and vote or donate money or whatever it is that I need to do, or stand up for what’s right if it’s in my immediate presence. But if it’s something that I can’t change, then why would I spend headspace on it? You know? So, I feel like I’m good at that, just being all right.” She continues, “I can change the things that I can change, but if I can’t, then I’m just gonna do what I can do to make my life the way I want it to be, and notice the good things and celebrate those things, and surround myself with people that are positive.”

Photo by Water & Gems Photography.

She tells me about friends who are never satisfied with where they are, that they are always thinking about their big goal. Although she respects them, she doesn’t go along with that way of thinking, as it leads to never being happy or proud of your accomplishments in the moment. This is one more indicator of her shortsightedness and how it works so well for her. “I feel like I have that balance where I am proud of myself for working hard and writing and staying engaged with my community. But I also having some dreams.” She admits to having some medium ones. “I would like to have an album of originals come out in the next year, and then I would love to do a small tour, maybe up and down the coast of California. That would be a more immediate goal because that’s something I think I could attain in the next year or two. But in terms of long-term goals, I don’t really know. I just would like to always be releasing music. I mean, I would love to be releasing an album every couple of years. I’d love for that to be a part of my life forever, and to always be gigging and growing.”

Her strategy becomes clear, “When you look so high and you’re not picking the lower apples, when you’re not focusing on smaller goals, it’s like you can’t reach it. It gets discouraging. So, I think I’m just trying to focus on smaller, more attainable goals.” I’m not knocking that.

When you look so high and you’re not picking the lower apples, when you’re not focusing on smaller goals, it’s like you can’t reach it.

It seems that Daugherty has paved her path well and has a clear vision, “If I could, I would love to just do music like this forever and ever because I love the way my life is right now. I’ve curated it to be very peaceful and include all the people I like. I have a lot of space to breathe and exercise and take care of myself and my home and my doggy and see my friends.” Worries about the future, keep her on her toes. “I am afraid that one day I won’t be booked as much. That is spooky, but it pushes me. You know, you can’t just skate by, you have to always grow and learn and not just play things safe. You have to always work on your craft.”

She reveals, “I think I’m always scared, and I feel like all songwriters are scared that this song is the best song I’ve ever written and will ever write. I feel like almost every song I write, I’m like, ‘Wow, I think it’s all downhill from here. I don’t think I can write a better song than this.’”

Well, I sure don’t see it that way. Yes, I’ve been there, but I can’t be convinced this isn’t still just barely the beginning, and it’s all looking up from here. I see the collision of talent and luck and gumption, hard work and focus, and yes, the alignment of stars and planets in the solar system, all of which have Kaylee Daugherty at their center.

Daugherty announces the inaugural Evenings on Adelaide Songwriter Showcase on Tuesday, February 18, 5:30-8pm in City Heights. In addition to Daugherty, this month features Stucky Leigh, Joe Summers, and Lauren Ong. Tickets are by donation; all proceeds go to musicians affected by the LA fires. RSVP here: https://www.eventbrite.com/e/evenings-on-adelaide-tickets-1215564438959?aff=oddtdtcreator