Beyond paying the bills, what makes a successful music career?

karaK. Kesselring: “Many people have different definitions of what makes a successful music career. One obvious answer is whether one can sustain themselves financially on their earnings as a musician. When I moved to Chicago in 1995 after completing a classical voice degree from the University of Iowa, I gave myself a three year deadline: If I couldn’t make a living as a musician, then it wasn’t meant to be and I’d try something else. I tended to gauge success in years and when my 25th birthday rolled around, I was working many colorful music jobs, putting the musical pieces together like a puzzle as the opportunities presented themselves.

I also have a degree in film and television production. When I was getting established in Chicago, I worked in operations for a year at CLTV in Oak Brook, IL. I was working in the over sensationalized world of “if it bleeds, it leads” media. That experience revealed to me that music was a better choice for me. As much as I loved my music school experience and enjoyed growing up in a liberal arts environment, I would not say that I was armed with the appropriate skill set necessary to become anything but a classical opera singer. I acquired the needed networking skills from other musicians and business people in Chicago. A valuable lesson I learned from my father, a salesman, was that you must always be looking two or three steps ahead for work. Don’t get too comfortable because something may end and you won’t know where your next paycheck is coming from.

Beyond paying the bills, a successful music career to me is simple. It really is about making people happy. It doesn’t matter if I’m playing “Tea for Two” at a retirement home, “Wind Beneath my Wings” for a wedding ceremony, or “Disco Inferno” for the 700th time with a jobbing band, my job is to make people happy. For the audience, it may be the happiest day of their lives or just a nice day among many. One of the great things about a music career is that you don’t have to take your job too seriously. People are not going to die from music. I know sometimes we hear music or have to play something we don’t like and think we’re in purgatory; but we are not saving anyone from cancer or a burning building. I think it’s important to keep that in perspective.

It is the stories that happen on gigs, the eccentric people I’ve met along the way, the drunks at the bar that I’ve talked to and sung for, these are the stories I can share with my children– stories that are too wild to even make up. I tell myself that I should write a book when I’m old and gray of what I’ve seen from the bandstand and what kinds of weird gigs I’ve actually gotten paid to do!

Being your own boss is nice, however, it can be difficult. A musician is thinking, eating, breathing, booking, or practicing music all day and night long. I often tell people, “I didn’t choose music, music chose me.” Like any small business owner, my job can become an all consuming enterprise. I have found that getting away from it–taking time off, or finding some variety–is crucial to appreciate it’s valor in my life. Versatility has been the key to my success. I think what keeps me working is my ability to be a jack of all trades. Many years of playing piano, guitar, and flute has helped me work on so many occasions. I love the fact that I can play synthesizers and sing in a dance band on Saturday night, sing in a classical choir Sunday morning, play flute in a Brazilian ensemble during the week, and teach children’s songs to the guitar. These kinds of challenges keep me on my toes and I’m never bored.

To me, success is not about being a rock star or being on the international music circuit (although I wouldn’t turn it down). Success is being a life long learner that is able to continue challenging myself in many different ways. This is why I continue to study different genres of music and why I still take lessons. It’s important to make connections with other musicians. I try to balance fun and lucrative gigs with creative projects. Success as a musician is not about acquiring things, but experiencing life, having the opportunity to travel and giving back to people. Success is the five year-old learning the note names for the first time. Success is performing “I Love You Truly” for the elderly couple dancing and singing along. Every performance is a new way to gauge success. You never know what you’re getting into when the phone rings…”

-Chicago Artists Resource

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