If you are one of Cailee Rae’s more than half a million Instagram followers, you know that the 18-year-old singer-songwriter is big on the idea of self-love. In April, she posted an image of a poem called “Hiding and Seeking” by the artist and poet Cleo Wade, with a caption that felt like a mission statement for the heart-driven, quirky pop music Cailee has been writing as of late, including her new single “Deeper” — a song about examining your life and demanding more fulfilling relationships.
“Last year … I didn’t know who I was anymore and I felt really lost,” she writes. “I felt like I had turned into someone I didn’t even recognize … I felt like I had let down people because of expectations that didn’t even exist. The only person that had those expectations was me. So one day I just let go. ... I posted what I wanted to post and didn’t care what people had to say. I let people who didn’t care about me drift away instead of trying to keep up with them. I let me just be ME. … It was the best thing I have ever done for myself. Don’t trap yourself in the image of who you are. Let yourself change and love yourself even if you disappoint others. … Now I look in the mirror and smile at the unexpected and love who I am.”
That confidence-affirming caption illustrates how refreshingly atypical a pop artist Cailee is. Rather than court “likes” and followers, she is true to herself as she delivers uplifting messages about self-acceptance, positivity, and honesty. The importance of those qualities became clear to Cailee within the last few years, as she navigated the choppy waters of social media fame. At 14, she launched her music career by posting covers on Vine and Instagram and quickly racked up followers, thanks to her sparkling voice and fresh-faced charisma. But she also felt trapped in a relentless cycle of toxic people-pleasing. “I’ve always been a good-vibes kind of girl, but it really took a toll on me,” she says. “Kids were all up in my comments with requests, and they’d unfollow me if I didn’t listen. It became like a job I didn’t want to do. I literally had real-life friends drop me when I’d take a break from posting and stop getting ‘likes.’”
In 2016, Cailee released her debut EP of original music, Overthinking, featuring the well-received single “Anchor,” which she wrote about overcoming her need to please others and the realization that the only person who could save her from the emptiness she felt was herself. “It was like I was trying to tell myself something when I was writing that song,” she says. “It was me saying, 'Look in front of you. You are creating this huge obstacle that doesn’t really need to be there.'” When she began suffering from physical anxiety, Cailee realized she had to make a change. “I re-centered my energy on myself and what really made me happy and everything just fell into place. My songwriting completely changed.”
Giving herself permission to be entirely authentic led Cailee to write “Deeper,” a song where she watches old lovers “disappear to nothing / disposable as chewing gum” and declares that she’s “not saying I’m some genius / But I’m smart enough to know I’m worth fighting for.” “The song is really about those deeper relationships that really impact you in a different way than those with people who just are in and out,” she says. “I want people to hear it and say, ‘Who in my life right now is just not worth it?’”
Maneuvering the shaky terrain of other people’s expectations is something Cailee grappled with growing up as an outgoing, music-minded kid in the sports-obsessed small town of Chesterfield, Missouri. ”I tried every single sport because I just wanted to be like the other kids — lacrosse, volleyball, cheerleading — but I was just awful,” she says with a laugh. Instead she spent time in her room listening to Ingrid Michaelson, Colbie Caillat, and Taylor Swift, whose song “You Belong With Me” inspired her to ask for a guitar in second grade. “I really connected with Taylor’s lyrics because she was a dorky, quirky kind of girl and I identified with that,” she says. Cailee taught herself some rudimentary chords and began writing songs, swearing to her mom that she was going to be a professional songwriter. “Everyone thought music was just something to keep me occupied as a kid, like playing a sport,” she says. “No one thought it would ever become what it did.”
Cailee’s belief in the importance in self-love sprung from early experiences getting razzed for being different, and also from watching her three older sisters walk through various life stages — hitting puberty, enduring break-ups, deciding on college. “I could see what to do and what not do,” she says. “That’s where the conversation started. I realized from watching them how much was missing.”
She continued to focus on her songwriting and recorded in professional studios wherever she got the chance. As her social media following grew, she began performing here and there and was instantly hooked. “Being able to look out at an audience that’s completely mesmerized is what got me so addicted to being an artist,” she says. “That’s when I was like, ‘I have to stop doing covers and create a real project.’ Overthinking was the first step. Each song sounds so different because it was me growing and figuring out how I wanted to sound. ‘Deeper’ is the next step where I’ve figured out exactly what I want to say and how I want to say it.”
These days, Cailee’s Instagram is an open and vulnerable dialogue with her fans about her thoughts and feelings. “Look, I’m all about emotions,” she says. “I think people run from them, but it’s okay to feel whatever you’re feeling and take that energy and put it somewhere else. When you’re done with an emotion, move on. That's why I love music. The days you feel sad, you turn on a sad song and everything feels right. You can turn on a happy song and you feel like you want to get up and dance. That’s what I want my music to be. I want people to be able to listen to it and connect with themselves and really feel whatever they have to feel and be able to move on."