WHEN I WAS A TEENAGER in suburban New Jersey, drowning in late-’80s malaise, my lifeline was the legendary radio DJ Vin Scelsa. On Sunday nights he hosted Idiot’s Delight, one of commercial radio’s last “free form” shows — meaning one of the last in which the DJ played whatever songs he felt like playing, without a set playlist dictated by marketing departments. A decade earlier, Scelsa had been one of the first DJs to play punk on air, and now he curated a show based on rock critic David Fricke’s three commandments: “Respect the elders. Embrace the new. Encourage the impractical and improbable, without bias.” During my last two years of high school he turned me on to bands as diverse as Pavement, The Undertones, The Bar-Kays, Bad Brains, and Blue Rodeo. But most important at the time, when I was first struck by the impulse to put pen to paper, Scelsa introduced me to songwriters: Fred Neil, Jimmy Webb, Townes Van Zandt, and dozens of others.

Once a month Scelsa hosted a songwriters circle at the Bottom Line in New York, called, appropriately, “A Bunch of Songwriters Sittin’ Around Singin’,” and he invited many of those artists onto his show to talk about their work and play live on air. I’d sit hunched over my portable tape deck, finger hovering above the record button, pressing down whenever his guests began to strum. I still have one of the old cassettes, squeaky now, but containing some of the best performances I’ve ever heard: Eric Andersen playing songs from an album that had been lost for 20 years and then discovered in Columbia’s vaults; Marshall Crenshaw playing the songs of honky-tonk legend Webb Pierce; Peter Holsapple and Chris Stamey of the dB’s playing songs by The Byrds’ Gene Clark, who had recently died.

But of all the great songwriters to appear on the show, I was most drawn to Willie Nile, not only because of his jaunty lyrics or his sweet nasal voice, but because of his story. Nile had been a downtown New York performer for almost a decade before releasing his first album in 1980, at the age of 32. Critically acclaimed, the album caught the attention of Pete Townshend, who invited Nile to open for The Who on their summer tour. A second album followed soon after, and Nile seemed on the verge of becoming the new Tom Petty, inheritor of The Byrds’ folk rock legacy. But before making it all the way to stardom, he ran into legal conflicts with his label. He stopped recording and performing for the next eight years.

And then, against all odds, he was rediscovered by a talent scout for Columbia, when he played and sang backup on a new track for the long-belated release of Eric Andersen’s lost album. Two years later he was putting out a new record of his own, with guest appearances by heavy-hitters like Richard Thompson, Loudon Wainwright III, and Roger McGuinn. The songs he played on Idiot’s Delight were rousing and catchy, the lyrics complex but optimistic. His career seemed ready to take off once more, to set him back on the path to becoming the new Tom Petty all over again. Yet on Vin Scelsa’s show he was funny and self-deprecating, making jokes about how quickly he’d fade back into obscurity.

No one else I knew had ever heard of him, but Nile was an appealing model for me at 17: an artist who’d stayed true to his vision, who’d struggled and suffered but whose hard work would ultimately have to pay off. I was sure he’d rise from the ashes and prove his doubters wrong.

Just be patient, I’d whisper to my miserable self as I scribbled awful lines of poetry or opening paragraphs of short stories that went nowhere. Keep your head down, stick with it, and you can be the next Willie Nile.

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I couldn’t stop thinking about Nile and Scelsa while reading songwriter Nick Jaina’s terrific new memoir, Get It While You Can, an extended meditation on failure in love and art making. Jaina, originally from Sacramento and now based in Portland, Oregon (though he’s on the road nearly three hundred days of every year), has released five albums to date, and like many musicians he has a small but loyal fan base, sells few records, and debates whether there’s any point in going on. He also is addicted, he says, to “impossible love,” the newest iteration of which, along with the theft of a favorite guitar, sends him into a melancholic tailspin that marks the occasion for writing the book.

To wrestle with heartbreak and to find new meaning in the life he’s dedicated to making music and sending his words into the air, he chooses to immerse himself in silence, attending a week-plus-long meditation retreat during which he’s forbidden to speak. There, instead of finding inner peace, he’s constantly irritated by “a douchebag in a windbreaker,” who fidgets beside him for 10 whole days. But the extended stretch without using his voice allows Jaina to reflect on his past, his parade of failed relationships, his grueling tours, his musical influences.

The book is structured as a series of vignettes, occasionally returning to the meditation retreat, but often roaming elsewhere, troubadour-style — to his college days in Monterey Bay; to New Orleans, where he first takes the stage; to Folsom Prison, where he and his band play several shows for inmates who aren’t rowdy and hooting (as they were for Johnny Cash), but rather polite and appreciative and interested in talking about the nuances of Jaina’s lyrics. Interspersed among these episodes is a collection of unsent love letters, along with riffs about being a clerical temp, about different types of sadness, about how to write a song.

The last of these captures Jaina’s combination of wry humor and pained yearning at its best. He offers up a list of 28 steps to songwriting, beginning with this one:

Pick a key. Be considerate of your bandmates’ wishes: keyboardists like to play in C. String players like to play in G. Horn players like to play in B flat. So. Let’s make it in C sharp. (It’s important to stick it to people who want everything to be easy.)

Step number six is simpler: “Find a canal and walk along it until you reach the end.” As is number 16: “Pretend you’ve forgotten how to tell time.” My favorite is number 24: “Take things too far. Miss the sarcasm. Shoot a dead horse. Make too many lists, make them too long. Drown yourself slowly.” He ends by saying,

This is how I write each and every one of my songs. If you want to find your own way there, go ahead. It might be better that way, actually, because then you’ll know how to get back.

By this time, deep into the book, the reader sees that it’s not so much about failure, but about the sacrifices that come with a creative life. In order to make something beautiful, Jaina knows, you have to give something up, and he willingly lets go of any certainty about the future.

But when is dedication to one’s art sacrifice, and when is it avoidance behavior? Jaina’s only real failure is his inability to resist his creative instincts when what’s called for is simply living. He spends an inordinate amount of energy writing love songs and love letters in order to try to make women fall for him, or fall deeper for him, or excuse him for his shortcomings, when he should instead be attending to the actual person in the bed. “Historically,” he eventually admits, “I have been more interested in expressing extreme cinematic emotions than in passing the salt shaker.” Even if he knows the love song is often a falsehood, less about honoring its subject than about showing off the noble sentiments and skilled wordplay of the songwriter, he can’t stop believing in “problems that can be fixed if you can just find the right chord change or metaphor.”

And it’s hard to blame him. What the book does so well is to let us feel how powerfully making pulls against living, how making can become living, though it may leave the maker wanting. No matter how much Jaina struggles, I find myself envious of his abilities. If I weren’t completely tone deaf, wouldn’t I, too, strum a guitar all day in an effort to break my own heart? Wouldn’t everyone?

Jaina’s true “impossible love” is the music itself. His real longing isn’t for fame or accolades but for artistic perfection that’s always just out of reach — that should always be just out of reach, because if you did reach it what would be the point of writing another song? The book’s finest moments are those in which Jaina writes love letters not to a romantic interest but to those who’ve toiled behind the microphone before him. He has a gorgeous chapter on Nina Simone’s performance at the Montreux Jazz Festival, and another on Ray Charles’s appearance on Johnny Cash’s variety show, where Ray sings “Ring of Fire” as if “it burns his mouth.”

When he’s looking away from the self, Jaina drops his charming but protective wryness and instead shifts into a register of wonder. He writes about his musical heroes with an attentive and lyrical analysis that’s as moving as it is precise:

Ray stops playing piano and looks up with joy and just spasms for a few seconds as the bass line keeps going. He lets out an “Aghh,” and then comes in right with the band. If you notated this moment musically on a score, there would be nothing in Ray’s part except for several rests, and yet it is one of the most fascinating things I’ve ever seen a musician do. He is just silently convulsing with the rhythm as though doing so were more important than any notes he could play.

Sometimes being overtaken by the music is more important than playing it. Sometimes living with what you’ve made, what others have made, is more important than making something new. This is what Jaina understands at the end of his 10-day retreat; and he’s probably known it all along. No doubt he’ll keep making music for his small but loyal audiences, despite the inevitability of failure, of falling short of the ideal. But maybe now he’ll be able to pause from time to time, to look up with joy and spasm for a second or two before jumping back into the melody.

In the end, Jaina’s book is a love song to music and to those who make it and live it. And that, I suppose, is why I had Vin Scelsa and Willie Nile in mind most of the way through — not because either has failed in his efforts, but because both have lived the life so deeply and passionately without obvious reward. If I were to compose such a song, for whom else would I write it? More than 20 years after my teenage Sundays in New Jersey, Scelsa still hosts Idiot’s Delight — no longer on commercial radio, but on Fordham University’s WFUV. He still respects the elders, embraces the new, and encourages the impractical and improbable without bias. Just last week he announced his coming retirement; he’ll play his last show May 2, after 47 years on the air. 

And Willie Nile is still making albums of rousing post-Byrds folk rock, though now he releases them on his own label. Moreover, at 66, he still tours relentlessly; this month he’ll play 10 dates in Spain before returning to the States for shows in Ossining, New York, and Maplewood, New Jersey. No one’s going to call him the new Tom Petty now — in fact, he’s older than Petty by a couple of years. But as long as he can still strum a guitar and belt into a microphone, why would he ever stop?

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Scott Nadelson is the author of three story collections, most recently Aftermath, as well as an autobiography, The Next Scott Nadelson: A Life in Progress.