Got questions for Little Bobby? Send them to dearlittlebobby@pyragraph.com.

Dear Little Bobby,

I’m stuck in a cycle of side jobs I don’t care about and feeling I never have the time to really develop my creative work to the point that I think I could actually make money from it. I’m a painter and trying to figure out how to finally get past making paintings that pile up in my studio and actually get shows and make something like a career as an artist. But without enough time and energy after work I don’t feel I’m moving my paintings forward creatively. Plus I still feel clueless about all the pricing and selling stuff; it’s all very overwhelming. I’ve tried mindfulness and it helps with the stress but I don’t feel any less stuck. How can I make a real leap in pursuing art as a career?

—Stuck In the Studio

Dear Stuck In the Studio,

If you are truly wondering how to make a “real leap” into a career of art, the only answer is to LEAP—jump, jump, jump. However, I am not advising you to do that. That is up to you. Have you looked before you jump? Have you REALLY looked at what you would be jumping into? Perhaps you have and that is why you have not jumped.

My art has not bankrupted me.

I have been a “semi-professional” musician for 15 years. I have made money, but not much, and I have put plenty of money into my music to turn around and make little in return. I have not yet broken even. But my art has not bankrupted me. I get to do something that I really love. Sometimes I spend money, sometimes I make money—either way, I keep doing it because I want to. And frequently, I need to.

Like you, I have struggled with whether or not to leap into a full-time artistic career. I have been taking baby steps, playing for a little bit of money, selling our albums, becoming a paid writer, having a successful Kickstarter and more. But these things have not yet fully paid for my mortgage so I keep working “straight jobs,” albeit with some glitter.

If you take more and more of these baby steps, you might not feel so clueless about the pricing and selling. Find what the steps are and take them, or that part of you which wants to move your “career” forward will NEVER be satisfied.

When I first moved to Albuquerque, I did not know anybody. I had never performed in public and I had never been in a band. But I decided to start a band (Shoulder Voices) with some friends. I decided to attend as many local shows as possible, to get to know people, get to know other bands, get to know the venues and the people that work in them. Those nights out were very valuable for making connections and of course for making friends, some of those friends went on to join the band later when we needed a bass player or a drummer.

After a few years of struggling to be heard and seen, I PUT ASIDE MY FEAR and auditioned for an established, fairly well-known local band (Unit 7 Drain). To my surprise, I was hired. I was then catapulted into learning a very different kind of music as well as growing as a musician. I suddenly found myself playing in front of hundreds of people instead of dozens. I was still not making enough money from music to pay my mortgage, but I learned a lot about booking shows, promoting shows, playing together with a group, going on tour and so much more. The “downside” was that I was playing songs that I had not written. In some respects, I was “just a sideman” in another person’s band—but it was very worthwhile. Years later I took those experiences back to my original band and have been far more successful because of those experiences.

I suggest that you take this mentality to as many art shows as possible. Meet people, ask lots of questions and perhaps have your own show someday. Maybe do some art which might not be your first choice (as I did when I joined that other band), but it could be something from which you learn A LOT.

And please do not confuse your art with a career in art. If your art is not a priority in and of itself, then you might as well be doing commercials. If you wish to be an artist, then make art. THEN if you want to make that your career, do that. Look before you leap. Be smart with your money. All of the common-sense things. But whatever you decide, do not be afraid.

—Little Bobby Tucker
“Andy Warhol, silver screen, Can’t tell them apart at all.” —David Bowie “Andy Warhol” 1971