Craig Finn is worried about getting old. He’s 40 and has played in bands for roughly the entirety of his adult life: Lifter Puller in the ’90s and The Hold Steady in the 2000s. His first solo album, Clear Heart Full Eyes, drops this week. And he’s worried about getting old. “There’s this youthful music,” Finn tells me while we sit at a marble-top table at a dimly lit bistro-type café near his apartment in Greenpoint, Brooklyn. “And then you’re this 40-year-old guy that’s trying to be OK about being 40, and not feel like you’re in an arrested development. Not feel like, ‘Oh, what am I doing.’”

A bit of context: There was a time in my life when the setup we’ve got going on here, this one-on-one with Finn, would have driven me, sputtering, into paroxysms of shock and joy. I still basically revere the guy; to me, The Hold Steady’s first two albums, 2004’s Almost Killed Me and 2005’s Separation Sunday, are perfect records. My passions have cooled a bit since I first started swooning for The Hold Steady; maybe I’ve even gained some professionalism. Which is good because I if I were still as slavishly geeked I probably wouldn’t be physically able to move my mouth to ask questions.

I moved to New York in the fall of 2006, about a month before The Hold Steady released their breakthrough third album, Boys and Girls in America. Back at college I was already deep into Almost and Separation, and all of a sudden it felt like everyone I knew was equally obsessed with them. Finn sang about “the way the whispers bit like fangs in the last hour of the parties” and how “we’re stumbling but I think we’re still in it,” and made heavy drinking with strangers in random places at ungodly hours — something that, as per first-year-in-New York-mandate, I was doing a lot of at the time — feel romantic and dangerous. We’d go see them all the time and they always used to close with “Killer Parties,” a jammy, beautiful slow-burner. Over fuzzy feedback, Finn laments: “If she says we partied/then I’m pretty sure we partied/I really don’t remember/I remember we departed from our bodies.” We’d fumble out, sweat-drenched and grinning.

“New York was on the hangover of that dance punk thing,” Finn recalls now. “And we came out, and it wasn’t our intention, but we were like, if that’s this, then this is that. We’re not DJs, not wearing skinny ties doing the” — and here he does a pretty good impersonation, complete with air drums, of the tsk–tsk of a hi-hat fill. “It’s rock. Meat and potatoes.”

Well, not only. Finn had a particular vision when forming The Hold Steady. The year was 2000, and he had moved to the city after the peaceful breakup of Lifter Puller (a band whose legend would grow only after their dissolution). Back home in Minneapolis he was working for American Express financial services, as a Series 7-accredited broker. In New York he got a job at a live music webcasting company called Digital Club Network. For two years, he didn’t play music. “I thought I was done,” he says. “I thought I had done it. I was putting pressure on myself to be an adult. Like, now I have to have a job.” Then he caught a show by Alabama rockers The Drive-By Truckers and changed his mind. “I remember thinking, ‘God, this looks so fun.’ I said, ‘I wanna be in a band again.’ And that’s how we got The Hold Steady.”

Around that same time Lifter Puller’s Tad Kubler left Los Angeles for New York, and they reconnected. “We wanted to have a rock band that was smart,” Finn says. “Those things have a hard time coexisting. But that’s the music I wanted to hear; that’s how I would describe the bands that I like. Smart rock that doesn’t sound like grad school.” The stakes, though, were extremely low: “We were having conversations about whether we were gonna play shows or not.” On Almost Killed Me’s “Positive Jam,” Finn recalls: “I got bored when I didn’t have a band. So I started a band, man.”

Almost Killed Me whipped up a small brood of believers. Very small: Spin voted it 2004’s Best Album You Didn’t Hear. “That list came out the first day of recording [for Separation Sunday],” Finn says. “We were like, ‘Let’s make a record someone hears this year,’ you know?” Sep Sunday, as Finn calls it, was heard.

The masses would come along later, but the critics were officially in the bag. “There was a good story there,” Finn says of the rush of media attention. “You know, these older guys, this last-chance thing. And there were a lot of words.” He’s talking about his early, inimitable lyrical style, a brimming torrent of sharpened story fragments and tossed-off references. On hand are the heartaches of a potent cast of marginalized fuck-ups who get down with over-the-counter medication: bartenders, hood rats, good-looking drifters, pimps who crib their names from Roman emperors, and Hallelujah, or Holly for short, the shattered Catholic party girl at the center of Sep Sunday. “She got screwed up by religion/she got screwed by soccer players,” Finn tells us of Holly, on “Stevie Nix. “She got high for the first time in the camps down by the banks of the Mississippi River/Lord, to be 17 forever.”

Finn’s words were decoded, praised, obsessed over. NPR footnoted Finn: “Ginger and Jack and four or five Feminax” — “Medication … recommended for relief of menstrual cramps. One would assume that it’s used here for something slightly more illicit.” In their rave review, Pitchfork called Finn “the poet laureate of the loading dock behind the mall where the runaway kids get together to sniff cheap coke at 5 a.m.” “I was just trying to throw as much stuff out as possible,” Finn says, downplaying the tricky, packed style. “It was a stream-of-consciousness thing.”

Finn is chattier when it comes to another topic from that era: debauchery. With a debt to their idols The Replacements, and as an implied nod to the overconsumption in their songs, The Hold Steady almost had a responsibility to booze heavy. “At the beginning, it was: This is what we do. We drink. We get on stage. And we fall apart.” They had help. “Everyone’s going crazy backstage. And we had this awful white-box truck that we’d drive around that was unsafe at any speed. We’d pile people in and take ‘em back to the hotel. We didn’t have a tour manager yet, so we were still interfacing with all the bar people. And those people can get you in trouble.” (Side note: Personally, I was heavily influenced by this Hold Steady press shot to start drinking Bud tall boys.)

It couldn’t last forever, though. “There’s a period where we really thought it could all be taken away at any time. ‘Well, if they’re gonna give us a bottle of whiskey, we better drink it.” Now, it’s like, ‘There’s lots of bottles of whiskey.’” Not that Finn is exactly sequestering himself these days. “I still have nights where I say, ‘I’m going out. There’s a bar across the street, and I’m gonna walk in there and I’m gonna buy people drinks.’ But it’s not every night. It can’t be.”

Finn doesn’t ascribe this to the intermittent sobriety, but the band’s also mellowed musically. More or less: Finn used to not sing; now he tries to sing. “I always had melodies in my head,” he says, “but when I listened to it I realized it wasn’t there on the tape. Every time we made a record, I try to make something a little more musical. To me, that meant connecting with the music rather than yelling over it.”

The new sound was debuted with 2008’s Stay Positive. Gone were Finn’s chockablock word towers that I was so obsessed with. Everything felt simpler, often bored down onto the titular message. Last year’s Heaven Is Whenever was a more accomplished album musically, but didn’t bring back Finn’s stream of consciousness. “I could hear a song and almost think [in that style],” Finn says of the shift. “You know, ‘She came out of the bar …’ And I’d heard a million Craig Finn parodies, and the fake Craig Finn Twitter, and you start to think, ‘Am I being a parody of myself?’”

I didn’t tell Finn I was more into his old shit, although I doubt he would have cared. The man doesn’t have much of an ego. I bring up keyboardist Franz Nicolay, who left the band before Heaven Is Whenever and later semi-bashed them in an interview, saying: “They have their one big idea — making literate, wordy lyrics over big anthemic rock.” Finn smiles, and says, “I wasn’t offended by that. He comes from a much more trained place, musician-wise, but we’re unlikely to make a quaint song cycle. I mean, I don’t play all these instruments. I’m not gonna go do something with a dance troupe.” And The Hold Steady record so regularly, he explains, because “if you wait four years for a record, you have to offer it up [for approval]. If you’re just like, ‘Hey, we got another 10 songs! You wanna hear ‘em?’ it takes the pressure off. ‘You don’t like this one? Cool. There’s another one coming next year.’”

His solo album was written with the same 9-to-5 attitude: “I quit drinking for Lent every year. So that’s when I said, maybe I’ll write a song every day, too.” Finn would wake up, go to the gym, and then work for a couple of hours at a desk in his apartment. He recorded his demo material, on a cheap acoustic guitar, directly into his laptop. “Rather than ‘I’m gonna try to write a great song,’ it was ‘I’m gonna try to write a song.’ So you start chipping away at it. Give it a week, open it back up again and say, ‘Well, the second verse needs work.’ It’s just punching the clock, which is not how you think of songwriting. But I felt, if I get to do this for a living, maybe I should take a responsible approach to it.” With a band put together by producer Mike McCarthy, Finn recorded the album in three weeks in the midst of Austin’s July heat. There was no grand statement, or creative splinter: The Hold Steady were on a break, and Finn wanted to record an album.

Finn borrowed the title from his beloved Friday Night Lights, inverting the Dillon Panthers’ catchphrase on purpose. “There’s this going away and coming aback thing that happens in FNL. And maybe because I’m a Midwesterner but a lot of my songs have dealt with that going and staying. I always felt when I lived in Minneapolis that everyone was moving. Even the people that never moved. A lot of people would talk about these moves. And that might not be Minneapolis. That might not be the Midwest. That might be your 20s.”

I ask him if the characters on Clear Heart come from the same place as those of his Hold Steady songs. “Some of them. A lot of the characters are people that are frustrated with where they’re at. They’re not where they want to be but they’re unable to do something about it. And that’s a really frustrating thing, especially when you get into your 30s. It’s something that’s certainly I’m attracted to with storytelling.”

But it’s not something you actually dealt with, I say. You succeeded.

“Well, look, if The Hold Steady hadn’t done something, I think it’s pretty easy for me to see myself in the office I worked at in in my 20s. And being unsatisfied.”

Finn’s talking about getting old. Again. His music, it seems like, is rooted in that vision: himself, sitting in a cubicle, stuck. And he’s right: His druggy weirdos are all stuck, somehow, fighting, and mostly failing, to make things right. On “Stevie Nix,” Finn catches up again with Holly when she’s 33, now “strung out on the scene.” She’s still hanging around at those camps down by the banks of the Mississippi River, but maybe not for much longer. And then we get the same refrain, tweaked: “Lord, to be 33 forever.”

Earlier, I’d stumbled across an old interview Finn did around the time of the release of Sep Sunday. He retells the tale about the origin of The Hold Steady, this time crediting seeing a reissued The Last Waltz in theaters as the spark. He cuts himself down by telling an anecdote about a botched attempt at recording a comedy album by “smoking as much weed and drinking as much Diet Coke as I could.” And then at one point, unbidden, he starts talking about the future of the band, and himself, and it turns out not much has changed in the last seven years. “Look at us,” Finn says. “We’re kinda old. I mean, I’m 33. Tad’s over 30. We want to do something that’s timeless.”