James Tillman on Taking the Big Leap

James Tillman Photo by Lloyd Foster
August 14, 2018

The up-and-coming singer ignored conventional wisdom to follow his dreams.

James Tillman thought he was going secure a living in the music industry by earning his MBA from UVA. But he’s an artist at heart, and his muse pulled him in a different direction. Since 2009 the D.C. native and rising soul star has been patiently and determinedly forging his way as a professional musician: playing, writing, collaborating, and playing some more. Here, he shares the story of how he found the courage to pursue his dream, what advice he had to ignore, and why he believes mistakes are an essential part of the growth process.

Disclaimer: The views and opinions expressed in this article are those of the author, and do not reflect the position of Spotify.

Several years ago, I made a decision that forever altered the course of my life and set me on my current artistic journey. In 2009, while attending the University of Virginia in Charlottesville, I felt that something was missing, and I left that school, one of the nation’s most prestigious, to pursue my dream of becoming an artist. It wasn’t an easy decision, and it definitely wasn’t my initial plan. When I first enrolled at UVA, I wanted to study music and business in hopes of one day working in the music industry. I had always been creative, playing in my high school band and attending open-mic nights around the D.C. area where I grew up, so this seemed like a smart, practical way for me to engage with something that I felt genuinely passionate about.

I was very excited to head down to Charlottesville my freshman year. I had done a bit of research and knew that it was the home of Red Light Management and that Dave Matthews started out there. I signed up for music history and theory courses as well as accounting ones. I planned to apply to the business school between my sophomore and junior years.

However, during my second year, I realized that school had boxed me into many experiences that weren’t fulfilling, so I refocused on the things I felt passionate about. I joined the student-run record label, Oluponya Records. I interned at the college radio station, and I took vocal lessons. But it still wasn’t enough. I was stuck in an accounting track somehow, interning for big-four accounting firms in the summer and nowhere near the international business track I had hoped for. My friends at the record label only wanted to jam after they studied.

So for my third year, I decided to transfer to the New School University in New York City. Everyone told me not to do it. My friends looked at me like I was crazy. My parents expressed their disappointment. My mentor, an entertainment attorney and alumnus of the school, told me not to make the move. She explained that after graduating from UVA, I’d be able to move anywhere I liked and create whatever I wanted. She may have been right, but what I realized is that the notion of “having time” is an illusion. Time waits for no one, and I didn’t want to shelve my dreams and pick music back up only after I’d gotten a professional 9-to-5 job.

New York City was no walk in the park (though I did take lots of walks through Central Park in that first year). I was alone and missing my friends. I felt like my music skills were nowhere near where I wanted them to be. I kept getting lost on the subway. Some of my classes felt like a joke compared to how rigorous things were at Virginia. I would catch myself spiraling into bouts of self-doubt.

Things didn’t perk up until about two or three months after I moved to the city. I had a chat with my mentor that gave me the spark I needed. During our phone conversation, I lamented that it felt like there was no way I would be able to fully adjust to what I had thrown myself into. My mentor’s reply was simple. “You’re right. There is no way. You have to make your way as you go.” I didn’t know it then, but those words set the tone for my career. I took responsibility and dove in, making my own way toward being the person and artist I’d always envisioned. I bought an acoustic guitar and a camera. I practiced and wrote music every night. I connected with like-minded musicians and began to jam regularly. The most important thing I learned along the way is to trust the process. It won’t always look like the ideal you have in mind. You have to set goals for yourself and embrace the risk that comes with pursuing what you desire.

This basically made magic happen. One of my buddies I had been jamming with was from Brazil and used to be deep in that music scene before relocating to New York. That led to me going down to that country to record my first EP. I befriended a DJ that lectured in one of my classes, and that led to a review from a notable media outlet that put my music on the radar globally. I learned to think bigger. I embraced streaming services like Spotify, and all the novel ways that people were connecting with and listening to music. I discovered a fanbase across the world and looked for opportunities to engage with it. So when it came time for me to release my next project, Silk Noise Reflex, I better understood the process and took advantage of all the data and insights available. I had fans in Japan, so I released a special-edition cd there. Cassettes were becoming cool again in Brooklyn, so I partnered with a friend to release a small run of tapes, which also ended up being popular in Japan. I used social media to engage and keep in contact with people supporting my music, which led to licensing opportunities and playing my first show in Tokyo this year.

One very basic thing I’ve learned is that when you’re finding your own way creatively, trial-and-error is always part of the process. Make friends with it. Embrace it. It's the best way to learn and grow. I was my own booking agent, manager, and PR person for a while. I definitely hit a few bumps along the way. I let details slip. I missed out on a big licensing opportunity because I tried to act like my own lawyer (that was funny). I worked with friends as “managers” and ended up botching my first opportunities for international shows (that was not so funny). I worked with and trusted agents that ended up burning me. A large part of music is about managing relationships. I realized that I wouldn’t achieve much working solely by myself and not being open to collaboration.

You have to figure out how to work with others in a way that works for you. I’ve met so many different types of people along this journey. I started to take responsibility for the things that happened because of who I was choosing to work with. The beauty is that because of these experiences I know a bit about all of these different areas that are essential for a career in music. I also seek out and partner with people that are knowledgeable and passionate like me. I am blessed to be building and working with a team of talented people. However, I retain my DIY ethos of embracing the new; thinking and dreaming big; and then making my own way toward the mark.

-James Tillman

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