Kayla Rae Jackson Quit Her Job, Broke Up and Found Herself as a Musician

Kayla Rae Jackson quit her job to produce music.
Kayla Rae Jackson quit her job to produce music. Stephen Granger
Singer-songwriter Kayla Rae Jackson had a feeling it was time to let go. It was Sunday, June 11, 2017. She had been working on new music for almost a year, intended for an album set to drop in August 2017. But now she decided to forgo the extra time she had planned to spend beefing up marketing and promotions for the EP; instead, she recorded three new songs in three days and released My Side of Our Story on June 11.

The title suggests the subject of the EP: love. Jackson had met a producer in August 2016; they’d fallen in love after working on music together, including songs on the EP such as “Love Is a Drug” and “Want It All.”
“All the songs about love going right were the songs he produced,” she says.

In December 2016, Jackson discovered that the producer had been lying to her. They spent a couple of months in limbo, in an on-again-off-again relationship, before she decided to put the past behind her and let go of the relationship and everything tied up in it — namely the EP.

Three days before she released the EP, “I decided to go for it and write out the last of my feelings on the situation,” Jackson says. “I was tired of being lied to, tired of being walked away from, and tired of feeling like other people had power over the way my day went. So I cried, wrote and recorded, and called it My Side, because there are always different sides to a situation, different perspectives and different truths. Mine led to the completion of the EP. You have a beginning, a middle and an end to every situation, and the end for me was June 11.”
Releasing the EP marked a significant turning point for Jackson. She put it online on SoundCloud at around one in the morning, realizing that in a matter of hours she would need to get ready to head to her job, where she worked as an administrator for a medical-app company.

She slept for a few hours, prepped for the day, drove to work, and realized she was finished with her job, too.
“I got to the parking lot of my job and thought, ‘Okay, Kayla, you just expressed yourself to death,’” she says about the album she had just produced. “‘You can go in here now and do something completely opposite. You can’t really talk to them about it.... You can put eight hours into something that is completely opposite from what you love, or you can just go home.’ So I wrote an e-mail and quit my job.”

A month later, Jackson is busier without a nine-to-five job than she was with one — even when she was pursuing music in her off time.

“Ever since I quit my job, it was as if something somewhere was waiting for me to do it,” Jackson says. “My calendar continues to fill up, and every day I’m offered a new opportunity. I find ways to make money. I have always worked to make sure I can eat and support myself.... Ever since I can remember, I’ve had a steady full-time job. So I’m like a kid on summer vacation right now. I’m loving it.”

As a kid, she watched her single mother’s unrelenting dedication to her work, as she labored around the clock providing for her kids. Jackson says her mom’s example proves that people can get anything they want or need, as long as they want it badly enough. Knowing this, Jackson maintained her patience as she rode out the transition from a steady job to pursuing her music full-time.

Jackson released her latest album after leaving a bad relationship. - STEPHEN GRANGER
Jackson released her latest album after leaving a bad relationship.
Stephen Granger
Her mom didn’t have a choice, Jackson says. “She couldn’t come home at night and tell her five kids she was tired, so she decided not to go to work and because of that we don’t have dinner. She had to go out there and make money every day, because she had a family to support. There was no option for her but to go into the world and fight for us to have a roof over our heads. Nobody in this world will hand you your dream or hand you your rent every month. You have to go out there and make that happen.”

Jackson’s belief in hard work and going after her goals was put to the test one day earlier this summer, after she left a store and returned to her car. Someone opened the passenger door, said hello, took her purse and ran off. It happened so quickly that she couldn’t chase the person. Although they stole her personal belongings, the robber left her with even more motivation to follow her musical pursuits, she says.

In life, success is “not about who deserves it more; it’s about who wants it more,” Jackson says. “It’s about who is willing to go the furthest to claim what is theirs. And since [the robbery], I decided that nobody is taking another thing from me: not my money, not my happiness, not my dream. Nothing. I want it more than anything.”

Along with her renewed determination to work toward her goals, she found herself resonating with the idea that she, and she alone, is responsible for her happiness. By ridding herself of a toxic romantic relationship and a job that was unfulfilling, she took control of her life instead of relinquishing it to others and expecting everything to go her way. Since embracing this idea, she says, things in her life are flowing as steadily as intended.

She says she used to think that “‘I need this nine-to-five to make a lot of money so I can afford the things I want and be happy,’ when in reality I didn’t need that nine-to-five to make money. I could make my own money. I wanted to wake up in the morning and have time to drink my smoothie, not rush out of the house so I could beat morning traffic. I wanted to take my time rising with the sun and going about my day with the things I wanted to do — not things I felt like I needed to do.”

One thing she has always aimed to do — whether playing solo or singing with her band, No Visible Flaws, in both Denver and Colorado Springs, where she grew up — is to be vulnerable with her music and expose the humanity lurking in a world where connecting with other people is difficult to do. This is something she says she accomplished on My Side of Our Story.

With the robbery, the EP and her pained relationship behind her, Jackson is embracing the unknown and looking forward to a fresh start, to continue performing, making new music and seeing what comes next.

“I heard something the other day: that you can handle whatever it is in the moment. It’s the fear of what might be that undoes us,” Jackson says. “It’s so true. You overthink what could come from this or what might not come from this... Just take it one moment at a time, because it’s your contemplation of the future that’s going to unravel you. Keep it together for now and move step by step. It’ll happen as it should. Somehow it always ends up working out.”

Kayla Rae Jackson at Test Kitchen
7:30 p.m. Thursday, July 27, Summit Music Hall, 1902 Blake Street, $15, 303-487-0111.

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Riley Cowing has been writing with Westword since July 2016. She is originally from Kansas City and graduated from the journalism school at the University of Missouri-Columbia. She enjoys connecting with local artists, drinking all types of espresso and loves any excuse to watch The Devil Wears Prada.
Contact: Riley Cowing