I’d wanted to teach for decades, but I waited, because I felt I had to deserve it. There’s a good reason Gandalf, Dumbledore, Yoda and Miyagi are years — centuries? — beyond us, and it’s because older teachers teach time.

So I went out to earn the holes in the elbows of my metaphorical cardigan sweater. I learned the craft of songwriting, lived the business of music, and, last semester, put my findings into “The Art and Business of Songwriting,” a class I taught at Yale.

Yale has never focused on popular music, and as I walked into the classroom for the first time, students literally shook my hand and thanked me for showing up. Everyone seemed to be on a different page: There were rank amateurs, people who’d already walked away from publishing deals, EDM remixers, bluegrass ukulele ringers and minimalist prodigies who needed paper extensions so they could tour conservatories.

What do you teach students like this? What do you teach Caitlin Pequignot, a sophomore in Molecular, Cellular and Developmental Biology who’s learning Chinese, has a YA novel just kinda sitting on her hard drive, and, when asked to write a song to a pre-existing video clip, turns in something as brilliantly heart-wrenching as this?

Caitlin Pequignot, “Still Beautiful to Me”

(After screening it in class, a fellow student summed up the mood: “Whoever’s going next? Good luck following that.”)

What you teach (besides “do more of that”) is context. There’s no understanding songwriting without it: that song intros existed so the DJ could tell you the time, weather and call letters of the station; that song length has a great deal to do with the amount of music LPs could hold; that the massive space subsequently available on CDs was experimented with, and abandoned when the Internet negated the format, as well as the entire concern over “space” and most of the foundations of the industry these 17 students wanted to learn about.

This is where context comes in, and I am uniquely qualified to tell the story of how to grow as an artist while the structure around me crumbles. My first live show after signing a record deal was Woodstock ’99, the festival that will always be known for (literally) burning down the idealism of the decades that preceded it. That same summer, Napster became a household word, and music sales have never recovered from the downloading revolution that followed.

Years later, in order to fund recordings on my own label, I worked at Blender, a general interest music magazine that was unable to serve the increasingly fragmented listening audience, and folded. From there, I moved to Spiralfrog.com, a revolutionary start up that sought to “compete with free” by offering ad-supported downloads in order to pay music creators. Unfortunately, record labels were not yet ready to grant the necessary licenses, and Spiralfrog died a grisly, lawsuit-laden death. (Labels have since embraced the inevitable, and granted similar licenses to the streaming services that presently exist.)

It seems that the better I get, the deeper the industry seems to sink. But through it all, I have found a way to produce, create, perform, and teach my craft. I would have loved to assemble a class dedicated solely to the art of the song, and to ascend weekly into some sort of commercial-free spaceship where I could introduce classic pop structures and show how they both satisfy and confound expectations. But instead, I felt a responsibility to teach survival, in the way that learning to walk is useless without also learning to breathe.

The artists I invited to speak in my class were chosen as much for their art as for the way they dialogued with business. Ryan Miller, lead singer of Guster, dedicated time to his band’s legacy as one of, if not the, first to create “street teams,” the mobilized inner circle of fans rewarded for proselytizing, postering colleges, calling radio stations, and spreading the word. Amanda Palmer, who raised $1 million on Kickstarter and had spoken the previous day at Harvard Business School, tweeted about the class, and I watched as my own name trended for a brief moment. Jonathan Coulton described his embrace of the Internet’s infinite real estate by recounting how he posted a song a week for a full year, and that by mid-summer he’d run out of his old bag of songwriting tricks, created a whole new bag, ballooned his catalog, and created a fervent fan base. Had this same class been taught when I was a student, most of our conversations about art would have been familiar; the conversations about business would have been utterly unrecognizable.

Students scribbled notes and tapped away on laptops, and I left every class sweaty, hoarse and hopeful that they were getting a broader picture of what they were getting into. Some of them know they want to be in music, but answering the question “How?” is a matter of survival.

I’ve been asked to teach next semester at NYU, in the Clive Davis School of Recorded Music, and the difference between the two universities couldn’t be starker. The place feels like music’s version of the school in X-Men: there are signed guitars, basses and drumheads hovering on the walls over standard-issue lockers I haven’t seen since high school. Classes are held in actual studios, with raked rows of chairs facing consoles where the “client” or “artist” will someday sit. Students already walk around in a preoccupied cloud, half navigating the hallway, half still solving the compression on a troublesome bass track. If you’ve ever tried to hold a conversation with someone who’s noodling on the guitar, you know the kind of haze I’m talking about.

I will be teaching a “tier” of songwriters who have completed prerequisites in theory and writing, and I won’t be discussing business at all — the school has an entire major devoted to it. In fact, my goal will be to strip the business immersion away from students prematurely focused on it to the detriment of their own artistic voices.

I haven’t met any of the students yet, but I know their analogues, people with hundreds of finished songs that would be “perfect for (name of popular artist),” but with none that are perfect for themselves. I’ve met the people they can become.

A producer friend I spoke to thinks pushing students to find their writing voices might be the even harder task, but I’m up for it. Because knowing the answer to the question “Why?” is a matter of survival, too.