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.

Between the Classroom and the Bandstand: Staying Relevant Even When Trends Aren't Built for You.

I’ve spent more than twenty years in academia. That might sound like a long time, but it didn’t feel like a career path. It felt like something I did alongside my real work—music.  Even though I don’t wear the facade of an academic—and no one who really knows me would call me one—the path I’ve walked through teaching, publishing, and shaping ideas carries that imprint.

In fact, I’ve been more productive—more visible—than many artists who live completely outside academia. That isn’t bragging. That’s reality. And part of the reason I’ve been able to do that is because the university gave me something the music industry wouldn’t: a long runway. Time.

They didn’t hire me because I was charting. They didn’t bring me in to generate buzz or profit. They wanted someone who could teach, serve the department, and help shape the direction of the program. In return, I had the space to do my work. No one asked me to be marketable. No one tried to fit me into a formula. That kind of freedom is rare.

In music, it’s different. People don’t support your work simply because it’s honest or original. Granting organizations may be an exception, but more often than not, support comes only if they believe it can sell. And if it doesn’t, they walk away. Record labels, booking agents, presenters—they’re all operating under the same basic logic: Will this make money? If the answer is no, then the meeting is over. That’s not cynical. That’s how they survive.

Years ago, a label head told me he regretted not recording more of my group. He’d only done one album with us. At the time, he didn’t think the sound would catch on. He was probably right. It didn’t check the usual boxes. So there was that familiar push: straighten it out, smooth the edges, give the people something they can digest easily. I didn’t take the bait, and he didn’t press the issue. He made his calculation and moved on.

That’s how this business works. It’s short-term by design. If you want something preserved for the long term, you’ll have to do it yourself.

Artists talk a lot about support. They wait around for someone to come along and believe in them. But the truth is, no one’s coming. If you want your work to last, if you think it matters, then you have to record it, release it, fund it, and stand by it. That’s not idealism. That’s basic responsibility. In music, there’s no tenure. The only thing that keeps you alive is the work.

Some years, people notice you. Other years, they forget you exist. That doesn’t matter. The important thing is to keep showing up. Keep putting the work out. Keep building. Because once you stop doing that, you disappear. Not figuratively. Literally.

I’ve said this before: look at the critics’ polls. Wynton Marsalis. Kenny Garrett. Cassandra Wilson. When I first hit the scene, these were names you couldn’t leave off the top five. Now? Their rankings barely make a dent. Not because they’re no longer good. Not because they stopped mattering. But because public attention moves on. Critics move on. Audiences move on. What remains is the body of work.

The rankings don’t mean much. Legacy is built through consistency, not applause.

The music business is full of moments that don’t add up. You do everything right, and nothing happens. You make your best work, and nobody hears it. Meanwhile, something younger—and sometimes safer— wins awards. That’s how it goes. But if you understand that from the start, you won’t be shocked when it happens. And you won’t let it stop you.

The goal isn’t to be popular. The goal is to be present. To stay in motion. To keep making music, keep telling your story, and keep adding to your archive—even if no one’s asking for it. Especially if no one’s asking for it.

And if you do that—if you stay in it long enough and remain honest about what you’re doing—it ends up being worth it. Maybe not financially. Maybe not in terms of praise. But in terms of purpose. In terms of clarity. In terms of building a life you don’t have to apologize for or explain away. Most people don’t get that far. They flame out early or drift into bitterness. But if you hold on, keep doing the work, and accept the trade-offs, you’ll look back and see it for what it is:

A life well lived.