The Cost of Playing: Investing in Music Without Losing Yourself

I’ve always been fascinated by the willingness of musicians to “pay to play,” so to speak. On one level, it’s understandable. We know there isn’t always a lot of money in jazz, and when we bring people on board — sidemen, engineers, designers — we want to respect their time and make sure they’re compensated. That part makes sense. But there’s a line somewhere, and I think it’s worth asking where that line is. Because while supporting the presentation of our own music is one thing, supporting the entire infrastructure of the industry just to keep it afloat is something else.

 How many institutions in the jazz world — magazines, grant organizations, publicists — would continue to function without the steady stream of money coming directly from artists? Take the musicians out of the equation, and many of these organizations would collapse. Yes, they review our records, they run features, they expand our reach. But we’re also the ones footing the bill.

Which leads to the deeper question: How much of what we pour into press campaigns, magazine ads, award submissions, and the rest actually builds something that lasts?

I don’t raise this to sound bitter. I’ve benefited from these systems myself. I’ve worked with first-rate publicists like Chris DiGirolamo and Lydia Liebman, and through that work I’ve been reviewed in DownBeat numerous times, received five-star reviews, been featured in the New York Times, and even heard my work reviewed on air by Kevin Whitehead on NPR. All of that has been gratifying. But after each milestone, I find myself asking, “Now what? Do I need another Times review? Another five stars? Is this really the kind of foundation that builds a future?”

Our financial worth should not only be determined by how much horn we’re playing. There was a time when bandleaders could reasonably expect touring and CD sales to provide a steady stream of income. Of course, a sideman might still come away in the black after a tour, but for the leader it’s often a different story — the expenses pile up, and breaking even is sometimes considered success. I’ve heard countless stories of leaders piling into vans, driving city to city, only to return with little or nothing to show for it financially.

And it wasn’t just the road. There was a time when selling CDs offered at least modest returns. You could count on distributors to get the music into stores, and if listeners wanted to hear it, they had to buy it. Add to that the royalties paid out when terrestrial radio was still the primary way music reached the public. Those performance rights checks weren’t enormous, but they represented a real income stream.

Contrast that with today, when most listeners expect to get music for free. And there aren’t many business models where the creator produces the product but doesn’t expect anyone to pay for it.

I guess if I had to come up with some justification, I would say that many musicians are most likely trying to figure out how to build a legacy more than they’re chasing financial independence. But at some point, we have to ask whether the traditional markers of success are enough.

And maybe part of the shift is understanding how the broader music industry has already adapted. These days, when major labels or top agencies sign artists, it’s often through what’s called a 360 deal—they’re not just signing the music. They’re taking a piece of everything: clothing lines, books, movie appearances, perfume, TV—whatever the artist touches that falls under the umbrella of entertainment. That model says a lot. It says the real value isn’t just in the album—it’s in the brand, the vision, the full creative identity of the artist. And maybe as jazz musicians, we should be thinking more along those lines, too.

To be clear, I don’t want to sound discouraging to younger musicians. One of my cardinal rules is never to dump on someone else’s hustle. My life motto has always been: get what you can get with what you’ve got. And I mean that. So by all means, pursue the reviews, the ads, the campaigns if they serve your goals. But also consider the bigger picture. The old paradigm — when record companies were the industry — is long gone. If we’re serious about building something sustainable, maybe it’s time we thought past it.

Plenty of musicians already are. I know artists who’ve built entire income streams from writing books, giving masterclasses, lecturing, and public speaking. Some have gotten entrepreneurial with instruments or gear. Others branch into clothing, branding, or other ventures that make sense with who they are. Personally, I’ve thought about pursuing writing — not just music-related but fiction as well — and even experimenting with selling some of my horn preparations. There are more avenues than ever to think broadly about what our art can generate.

Because at the end of the day, if everything comes down to a musician’s handshake at the end of the night, we’re not really setting ourselves up for long-term success.

So what can we do? For me, it comes down to a few steps:

    •    Be intentional. Ask yourself whether each dollar or hour you invest is actually building something lasting.

    •    Diversify. Don’t let your worth be measured only by the gigs you play. Explore writing, teaching, entrepreneurial ventures — anything that reflects your broader vision.

    •    Protect your legacy. Think beyond the short-term hustle. What will remain after the campaign ends, after the tour is over?

    •    Stay open. The industry is shifting every day. Don’t get stuck in an old model just because that’s how it was always done.

None of this is about abandoning the horn or the stage. It’s about making sure that the energy we pour into the music is matched by a strategy that allows the music, and the musician, to endure.