Today we’d like to introduce you to Kaylee Daugherty.
Hi Kaylee, so excited to have you on the platform. So, before we get into questions about your work life, maybe you can bring our readers up to speed on your story and how you got to where you are today.
While I did not come from a musical family, listening to my dad play guitar in the evenings of his days off gave me my first love of music. I started out doing music in church, as do many musicians, and also band starting in 4th grade. I did percussion because it was the cheapest instrument (sticks and a book were the only expenses). It definitely laid the foundation of what I do professionally today, though we were terrible. We got a new director my junior year in band, and he made us play one song the entire marching season since we “just couldn’t get it”– ‘Thriller’ by Michael Jackson. Though we barely competed, the community felt between the musicians was my favorite part of high school and has evolved into my favorite part of life. If I knew then that I would be performing professionally, I would have majored in music after highschool, but it didn’t even come to mind as an option to me. I was the best on our drumline, but we sucked overall so that wasn’t very meaningful. I thought only prodigies did music professionally. I had also always thought I had to make the world proud of me by directly making it a better place, especially being a first-generation college student knowing I had opportunities my parents didn’t, so I started university in pre-med. When I saw in my lab partner what it looked like to truly enjoy science and saw in myself the opposite, I switched to the route of special education, a less direct way to still “make the world a better place” but still a way to pay a due I thought I owed.
After I got my degree in Education and was awaiting grad school admission, I was a worship leader and accidentally got connected to the jazz scene through our worship team. I went to their gigs and jams and was quickly inserted into a culture that welcomed me and excited me, and taught me so much. I still felt like I could only enjoy from the sidelines since it seemed everyone in the scene had been seriously studying jazz, or at least music since they were kids. At the time I was 23, never having taken lessons, so it seemed like I could never catch up. With encouragement from my new friends in the scene, I jumped in, and it has become not just my favorite part of life but my life in its near entirety. It brought me a new community, passion, and an avenue of daily growth that switched my focus from the world being proud of me to me being proud of me. I now commute to San Diego from my home in Banning most weekends for my 2-3 weekly gigs, which is a bit of a pain to my gas tank but what makes my life whole.
Would you say it’s been a smooth road, and if not, what are some of the biggest challenges you’ve faced along the way?
Nearly all the struggles as a creative are mental. Yes, my ability to sing depends on my health, which fluctuates, and my income depends on my gig flow, which also fluctuates, but the deeper challenges I face lie in my head. I have taught music lessons to a handful of students for the past half year, while I myself have only taken a few lessons, those being in the last year. I have learned a lot about vocal pedagogy while teaching them. The imposter syndrome can make me work harder to catch up to my peers, but it can also be discouraging. However, there has never been an easier time for anyone to learn anything, anywhere, than in 2023. The amount of free, high-quality resources at our disposal via the internet is astounding, though overwhelming. At times I have been stalled by the sheer question of where to start, but I know that any exploration is better than a stand-still.
The idea of playing standards vs. originals is also a point of contention. Some think playing standards is a lazy way to skate through gigs; some think it’s preservation of art that will die if we don’t keep them alive. Some think it’s for fun and not to be taken seriously, some people think it is the only important thing in life. At gigs, I can sing a very difficult song. I have poured my heart into practicing for months and get radio silence from the audience, but once I play “Girl From Ipanema,” suddenly, people are pleased. It can be frustrating feeling like effort is useless when what people want and will tip for is the same 10 songs that I have grown to despise over my past four years of gigging. I find myself expecting to be background music, often competing with the DJ bumping twice as loud next door, to the point where I am surprised when people are actually listening.
I have been trying to write more lately, and I have found it to be a very vulnerable process. It’s like ripping a page from your diary and reading it to strangers. You can hide behind a standard because someone else wrote it–if they don’t like it, well hey, tell that to Gershwin. But if they don’t care for my original tune, that’s like saying they don’t care for my soul. Every part of it is me– the changes, melody, lyrics, and the channel it passes through in performance. Lately, I have been trying to write on the basis of diligence rather than inspiration. I am realizing that inspiration comes so inconsistently, but when I make it a point to sit down and write, something always comes out, even if it is small or something I will later toss out. I am also realizing that keeping my mind satiated with constant stimuli does not give me space for original thought, and am trying to combat that. Ideas come from being bored, and I am trying to allow myself space to be bored. Attending Writer’s Round, a weekly open mic songwriters-in-the-round community at the Ould Sod in San Diego has really inspired me to be more dedicated to songwriting. Having a place to share tunes, get feedback, hear others’ ideas, and just absorb their passion is very motivating. I hope to record my first EP of originals in the fall to be released in the winter. This is very exciting for me, though daunting as it is hard to shake the thought that there is nothing left to be said.
Thanks – so, what else should our readers know about your work and what you’re currently focused on?
I am a jazz singer specializing in singing in Spanish and Portuguese. There are few Portuguese singers in San Diego, so I am happy to have found a niche I can dig into. I am really proud to have stuck with language learning–Spanish from high school, and Portuguese for the last 4 years through Duolingo (shoutout to my main owl). I have had good practice this last year playing a weekly Latin jazz residency at Madison on Park in San Diego with Irving Flores, one of San Diego’s best pianists and one of my main mentors. I also have an Elis Regina tribute coming up May 6th at the Jazz Lounge in San Diego with arrangements by Irving. I am very excited for this as it will be a very polished show in such a special venue, performing music from one of my favorite artists–Elis is one of the premier voices of Bossa Nova. You can buy tickets here:
https://www.simpletix.com/e/tribute-to-elis-regina-tickets-129022.
What matters most to you? Why?
Community. The bond felt between musicians in the thick of a tune is unlike any other. You can meet someone for the first time, be of vastly different backgrounds, ages, creeds, even language, and connect instantly through music. The community in San Diego specifically is so tight-knit and supportive compared to other artist communities that are often more cut-throat. Another’s success is celebrated as our own success because it is a success on behalf of the whole community.
Expression. Our hearts are saved from breaking by bursting in collective creation.
Healing. I recognize that music is the ultimate healer, and remind myself of this before every gig. Music can be the highlight of people’s days, weeks, lives. It can be a turning point for those struggling. I have seen music bring people to tears repeatedly, myself regularly. There are hundreds of music venues open on any given Saturday night in San Diego–if only the 3 best singers ever gigged, there would be so much less live music and opportunities for these healing moments to occur. There is room for everyone at the table. You don’t have to be the best to touch others; you just have to be real. Even in special education, my nonverbal kiddos often sing before they speak and respond to music more than any other avenue of education. Music is magic, and we are not just musicians but magicians.
Contact Info:
- Website: https://www.kayleedaughertymusic.com/
- Instagram: https://www.instagram.com/kayleedaughertymusic/
- Facebook: https://www.facebook.com/kayleedaughertymusic
- Youtube: https://www.youtube.com/@kayleedaugherty1165/featured

Image Credits
Toni Spero Photography
Manuel Cruces
Camberos Photography
Anastasya Photography
Water and Gems Photography
