I’ve been really enjoying a posthumous release from Miles Davis – That’s What Happened 1982 – 1985, The Bootleg Series, Vol. 7. It’s a great collection of live and studio recordings that Miles did during this time, most of which have been heretofore unreleased. It’s a brilliant historical artifact of a time in Miles’ career that is often overlooked by the jazz intelligencia, due to its heavy connection to pop music. It’s also a period of his career that is near and dear to my heart.

You see, I was alive during this time and I was very aware of Miles’ music (I guess that makes me a historial artifact too, but that’s a conversation for another time). In fact, everyone around me was very in tune with Miles and his work. He’s one of the legends of jazz, and at the time, he was still alive, so everyone was watching him. I vividly remember talking with both my professors and my peers about Miles in college. Everybody had an opinion about his music, and for better or worse, I was thrilled to jump into the conversation.

The conversations often went something like this: “Miles was a genius. His work in the fifties and sixties were absolutely brilliant. He pushed jazz in so many different directions. And now, he really knows how to get the money.” The first part was said with admiration and respect while the last part was said with a wink and a nudge. Because everyone knew that Miles was an artist in the fifties and sixties, but by the eighties, he had sold out his artistry in deference to making money.

Personally, I don’t think these assumptions were fair; I never met Miles and I certainly never talked with him about this, but I think that my peers and I were misunderstanding his intentions. I think that he pursued pop music and made a product that was appealing to the widest population of listeners. I think that he did it in a way that connected to his more traditional jazz roots, bringing in pieces of the jazz vocabulary, albeit in a more defined harmonic space. I believe that he sincerely tried to find a common ground between the two musical worlds, honestly attempting to create something new. Of course, his larger than life personality made him a massive pop star, but he also just oozed jazz cool. The Miles Davis of the eighties was different than the Miles Davis of the fifties, but he brought the aesthetics of that time period into the modern age.

Don’t get me wrong, I do think that Miles was invested in making money and I think he made some very purposeful musical moves for financial gain. But let’s be real for a minute – music was Miles’ business and he had to make money from it. He saw the winds of change back in the late sixties and knew that in order to make money, he would have to embrace rock and funk; a fact that only became more prevalent in the eighties when he brought pop music and modern production techniques into the mix. And he probably sacrificed some musical ideals in order to make recordings that would sell money or get booked at the highest profile (and highest paying) festivals. Miles had bills to pay just like the rest of us, so he had to make music that payed those bills.

But let’s reframe this for a minute – while Miles was making money and blending musical worlds, he was also connecting with a whole lot of people. He saw that there was an audience willing to pay for jazz with a pop music edge, but he also saw the reason they would pay for it – that was the music that they wanted to hear. The music met his needs – it allowed him to blend musical worlds and it led to financial success – but he was making the music for the audience. It belonged to his audience just as much as it belonged to him and the people knew it. They loved Miles for who he was, but they loved him even more because he heard their musical desires and gave them what they wanted.

Isn’t this the whole goal of music making – to make a connection with people? We – or maybe its just me – get so caught up in the idea of being an artist and only creating the art that we want. If we go outside that narrow idea of what the art should be, or even worse, we make a concession to connect with people, then we are “selling out.” It’s assumed that we don’t care about our art, only the bottom line. If we really cared about our art, we would ignore any audience desires and make what we want. That’s pretty self-centered if you ask me; it doesn’t lead to a connection with anyone.

I was really I’ve been struggling with this idea a lot lately as I’ve stretched my musical and artistic efforts in different directions.

It was especially apparent as I created by latest electronic piece, “Gratitude”, which was far away from the jazz aesthetics that I’ve admired for so long. This song was based on one chord. Just so I’m clear, that’s not jazz vocabulary; this was just one chord. Even worse – it used lush synthesizer sounds that leaned into the realm of New Age textures, which once again, stepped outside the more rhythmic and precise sounds found in a jazz setting. It was so different from the music I’ve studied and loved for so long.

Then something a little scary happened after I created it – I liked it and other people liked it. Full disclosure – I purposefully pursued this approach because it seemed like the best way to express the emotions that I was feeling. Strangely enough, I could have expressed this emotion in a more traditional jazz setting, but I thought this was more appropriate. And I enjoyed both the process and the product. Then I started getting positive feedback from “Gratitude”, almost more positive feedback than I regularly get from my more jazz oriented videos. There was something in there that rubbed me the wrong way, but I enjoy connecting with people, so it was nice. But it was the next thought that scared me senseless.

“If people are enjoying this so much, maybe I should make more music like this.”

Right away, the critic in my head shut me down and called me a sell out. I cringed at the thought – how dare I sacrifice my art because people like something different? How dare they like something different. If I was a real artist, I would just make my art and ignore the world. If they are lucky, they can find their way into my music and listen on my terms. I will not settle for anything less.

But then I remembered Miles.

Couldn’t I experiment? Couldn’t I blend my past experience with this setting? I could still make jazz oriented music if I leaned into the electronic space a little, right? I could do both. And even better, I could connect with more people. That’s what music is about, right?

As I write this, my inner critic is screaming at me, but I’m going to ignore them for a moment. I want to connect with people, so I’m going to continue to explore electronic music alongside my long time love of jazz and Afro-Cuban music. And I might even lean it more towards the sounds and textures that people enjoy as they share their opinions. Because I want to connect with people over music, even if I have to step outside my comfort zone and be something slightly different. If I find more success in that side of my musical output, I’ll be happy with that. I’ll take connection every time.

That’s one of the many lessons that I learned from Miles.