Does anyone actually like their job?

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1:53When I was in my 20s, I had this recurring fantasy. This little movie I'd play myself in my mind to calm down when my brain was too jittery and I couldn't sleep. I'd picture myself walking down my block late at night, completely alone, when all of a sudden this guy would come around the corner. And it would be me, but older. And I'd have just a moment in passing to ask him, does it work out? And this older, grizzled version of me would just, like, sagely nod his head and then disappear, presumably into the fog of night. Just to be clear, this anxiety I had about my future, it was not about my health or my friend's health or who was going to be president.

2:33From about 2006 to 2014, what I fervently stayed up all night thinking about was whether one day I would get to do the thing I'm doing exactly right now in this moment. I wanted to tell stories for a living. I was living in New York, a college dropout, with a decent temp job doing research and editing for a radio journalist. but I wanted to tell stories myself. I wanted this the way people forced underwater want oxygen. I was convinced that if I could have this, every other problem would take care of itself, and I'd just be in a permanent state of happiness. Like, I would not feel pain. Taking ecstasy would be like drinking room-temperature tap water.

3:1324-7 nirvana, if I could just get a job telling true, reasonably amusing stories. My life had a focus. Perhaps too much focus. Because on the flip side, I was also convinced that if this didn't happen, no matter what else worked out, I would be miserable. There's a word for this toxic condition, this poisonous, all-or-nothing kind of thinking. It's called ambition. You get a glimpse of a life you want. You fix on it. And from that moment on, you feel intense, all-over pain every moment you're not there. I now know that despair is not a rare feature of anyone's 20s. Even very fortunate people often spend that decade stuck in a life they don't want, without a clear path to the one they'd prefer.

4:01But that despair felt, like most things about life then, completely unique to me. I couldn't find a container that could hold it. My boss at the time had this sign above their desk that said, quote, The sun shone, having no alternative, on the nothing new. I became convinced that everyone in a job was miserable, that the entire world was filled with people who spent Friday dreading Monday, that anyone who claimed to like their job was just lying to me personally, for what reason, I'm not sure. But then I heard about this band.

4:45They were called The Hold Steady. Indie rock music, the kind of band that seems to have zero casual fans. Either you've seen them a hundred times or you don't really get it. I got it. We're all steady, Evo City. You're up to your neck in the swag-wet confetti. If you want to get a little bit light in the headie, it's gonna have to get a little bit happy. The songs I thought were perfect. The story is about down-and-out partiers in America. People with fucked up lives who'd slid far off the path of their own dreams, but still had a sense of humor about it. Constitutionally unable to enjoy something without becoming obsessed with it, I got very obsessed with the band.

5:28And in particular, with this one small part of their mythology. I'd heard about how the singer, Craig Finn, had supposedly had a very strange path into his music career. And the story of that path gave me a kind of hope. What I'd heard on the internet was that before the Hold Steady, Craig Finn had languished in a drab office job. In one version of the story, he was an IT guy at Goldman Sachs. In this legend, it was believable because Finn was a balding, horn-rimmed, glass-swearing guy with a pretty nasal voice. The joke in the reviews of the band was sometimes that he actually looked more like an accountant than a rock singer.

6:07In the version of the story I'd heard, he'd basically become an accountant, and he'd had to make peace with it. But then, after years languishing in a job he didn't want, he started this new band, just for fun, The Hold Steady. And that band had taken off. It had rescued him from his life. And there was a little more evidence for this story. The story of a guy who late in life had escaped a job he hated and found one he loved. When I'd see them play live over and over again, there was this thing he'd almost always do towards the end of the set. He started to tell stories. and then on the stage he'd offer something that felt almost like a prayer man i say the same thing almost every night i don't i don't i'm not fooling anyone but i only say it because it's true where he would just express pure gratitude that his life had worked out that he got to do his job for a living there is so much joy in what we do up here I want to thank you for being here to share that joy with us.

7:06And I came to understand that maybe I was going to all these concerts really just for that moment. Maybe I really needed to believe that someone really did love his job. That everybody else wasn't just faking it the way I was faking it. But being constitutionally incapable of not becoming obsessed with things, I started to think about it too much. And I started to wonder, like really wonder, what if Craig Finn was lying? Because I knew that even most dream jobs eventually become jobs. They become onerous. And if Craig Finn had ever just once publicly said in some interview that he loved his job, and if people had responded to that, he would have been bound to that fiction forever.

7:52For years, stuck in my own unhappiness, I wondered about his happiness. Wondered if it was real. I would plot and scheme about ways to ask him about it where I might get a real answer. In 2014, I bid in a charity auction where the prize was you got to go jogging with Craig Finn. I had this idea that if I asked him when he was sort of winded, then I'd get a real answer. I won the auction, but I never sent the email to book the actual run. The band's manager even followed up with me, but I ducked his emails. I chickened out. Whenever I'd see Craig Finn's name after that, I'd feel this little jolt of embarrassment and regret.

8:32In the years that followed, a lot of things would happen in my life. Over a decade later, I think I'm now actually the age I was picturing back then when I couldn't sleep, that grizzled older version of myself. But now, with a podcast, where I get to call people and ask them all sorts of questions. Questions about ambition, questions about jobs, questions about how to survive as a person.

8:57So, after the break, Craig Finn.

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11:30Welcome back to the show. A few months ago, I tried just sending Craig Finn an email, telling him where I was coming from, and asking if he might be up for what could be a slightly unusual conversation. He said he was game. Okay, so I think my first question for you is just, can you give me a picture of your early life? How old were you when you first decided the job you wanted was musician? I think, I mean, I remember telling my babysitter when I was really young that I wanted to be a rock and roll singer. Like when I was like, I don't know, eight. S-A-T-U-R-D-A-Y I was listening to bands like The Bay City Rollers and Kiss and getting really enthused about music and also the monkeys who are on TV.

12:25It looked like that was the best job. It looks like I think there was the camaraderie of being in a band that looked fun. Yeah. The ability to burst into song. It seemed like girls liked guys in bands. The whole thing looked pretty great. And I was a very mild-mannered, nerdy kid, so it didn't seem like I was destined for it. But it's what I wanted, and I think it led me before too long, probably, to ask for an electric guitar. And what did your parents do? Oh, my dad worked for Ernst & Young, the accounting firm, and my mom was a homemaker since I was born. So they were not rock and roll people, but they were very supportive.

13:06And maybe I was half saying, I'll probably work in the music industry. And did you feel like, I think one of the things that people use the word ambition, and I think what's weird about my relationship to that word is that it sounds like a powerful feeling. It's like, I'm going to do all this stuff. But whenever I've experienced it, it's been like a painful feeling. It's like, I want this thing. I see a huge gap between my life and the life I want. And I feel like I'm on the other side of the glass and it like hurts. Like, did you feel that way towards music? Yeah. I mean, one thing I can point to is like in college, I went to Boston College and I was writing for the school newspaper.

13:43I was like reviewing records. And that was, you know, I did that and maybe I did okay at it. But I got the feeling that that wasn't the side of it I wanted to be on. And then a friend of mine had started a booking agency. And she was booking cool bands and maybe a little more part of this indie scene than I was. And I started hanging out with her and helping her with some of her stuff. And again, it just got me closer to bands, made me realize what I wanted to do was to just play my own songs and have a band rather than do sort of this, you know, whatever involves booking a tour. Now turn your stereo up and your TV on to cable channel six.

14:23Here's your host, Amy Dolley. This video clip is from December 1997. A 26-year-old Craig Finn is playing with his up-and-coming band, Lifter Puller, on live public television in St. Cloud. Ladies and gentlemen, may I present to you Lifter Puller on Monday Night Live. Thereafter, we'll refer to this. In the video, Craig Venn looks quite young And like a guy who maybe did not have time to change after work He's wearing a red Oxford tucked into chinos Playing a Telecaster covered in stickers I will say, Lifter Puller, I do not love the way I would love what would come later The Hold Steady Honestly, it might just be that the lyrics are harder to make out.

15:12But I do feel like I can already hear some of what Craig Finn is going to do really well in this next band. He's going to tell these gossipy stories about an underground world that he has this magic ability to conjure. This seedy, sleazy underbelly of Minneapolis that might only exist in Craig Finn's own imagination.

15:41People here are always waking up high and bewildered on intersections that alliterate. The drug dealers cross paths with the sorority girls. Everybody wonders about this mysterious fire set at a nightclub called the Nice Nice. It's a world you can sink into. The characters from one song sometimes cameo in another. By the time Lifter Puller started in earnest, Craig Finn had decided not to pursue his music industry job as a booking agent. In his mind, it just didn't feel right to be working in the industry while simultaneously trying to make it as a musician. Like, maybe people wouldn't take him seriously.

16:16So he got a real day job. And the job he got, not what you'd expect from a man staying up all night in clubs, singing songs about arsonists and drug dealers and pimps. It wasn't the one I'd heard. He wasn't an IT guy at Goldman Sachs. But honestly, it was pretty close. I started working at American Express Financial Advisors, which has a big campus downtown Minneapolis. So you were working at American Express Financial Advisors while you were in Lifter Puller? Yeah, yeah. It was really kind of an interesting, spectacular place. I started out in the annuities department, and people would call in, and you'd tell them their balance, and you'd do small transactions for them.

16:55You know, I'd wear a headset mic, and there'd be like this football field-sized office, right? Like, you know, and everyone had their little cubicle. And there were a lot of young people that worked there. So there was its own scene, you know? I mean – What was the scene like? It was weird, you know? I mean, it was like the office kind of experience that in some ways is very stereotypical. Like you'd have a Christmas party and people would misbehave, you know? I remember there were these guys that I'd hang out with sometimes, and they would like go out almost every night, and then they'd come in and they'd rate their hangovers.

17:28and they would like and you had we had like an intranet system you know like so you could like talk to each other and I can't remember what the level I think level six was you threw up at work that's great so that's so such a low number throwing up at work yeah I mean and it's funny the thing was is there would be a tax season where people would need their tax forms and whatever yeah and it would get really busy and And it was really awful. Like, people would have to wait on hold for, like, a long time before they talked to you. They'd be really angry when they got you. Yeah. And so, like, I remember during that period each year not wanting to go to work.

18:11Like, lying in bed and being like, I don't want to go there today, you know? A lot of people, faced with a job they don't love, survive just by living in their imaginations or looking forward to nights and weekends. Craig Vinn, for whatever reason, decided the way he would thrive at American Express Financial Advisors was he would just apply himself to the job more deeply. He realized there were these tests he could take to climb up the corporate ladder. There kind of was like a company-wide directive that you had to pass what they called a Series 6 exam, which is a regulatory thing. Okay. And a lot of people had problems passing that exam.

18:47And I think a lot of people were in a different place than I do. or their parents, et cetera, and they just didn't have time to deal with it. I was able to pass it pretty easy. And so I said, wait a minute, I'm gonna go get this Series 7. Listening to Craig Finn talk about all this, I have a moment that feels like genuine disassociation. This person who I admire so much, his ability to tell stories, his ability to make music that has sustained me as a human. He's talking about his LinkedIn corporate accomplishments with such straightforward, normal pride. It feels like we've slipped and fallen into some other multiverse.

19:20where I'm now a hiring manager trying to figure out if Craig Finn would be a good fit synergy-wise for my team. Series 7 allows you to trade stocks and bonds. So I went and studied for that, and then I got Series 24, which for every amount of Series 7s you have, you need a Series 24 to kind of sign off on their transactions. So I saw this exam-taking as a way to kind of make myself indispensable. Yeah. And through that, I moved up to a wealth management area. And so you're not, were you, when you would go into work at your day job, was it like, it sounds like it felt fine. Like, it doesn't sound like it was like a life of quiet desperation.

20:00It was like an insurance policy that was supporting. Yeah, it was exactly that. And it allowed for some stability. I mean, you know, my bandmates largely were doing more like, you know, freelance stuff. They were like catering and things like that. And that felt more stressful to me than getting a paycheck every two weeks. So just to remind you of the question I'd actually come here to answer, I'd wanted to know if Craig Finn liked his job as an indie rock star. It had never occurred to me to ask the much stranger question of, before he was an indie rock musician, did Craig Finn like his job working at American Express?

20:38But he had. He liked it fine. So the first thing that surprised me is that Craig Finn, like pretty much every person I've ever met, was better adjusted in his 20s than I was. When he looked at his life then, what he saw was a steady paycheck to let him focus on his real passion, Lifter Puller, a band that was becoming Minneapolis famous. One day he got a call from a guy above him on the Amex corporate ladder. There was a guy who called down and said, hey, do you follow local music at all? And I was like, yeah, a bit. And he goes, there's a band called Lifter Puller and their singer has the same name as you.

21:13And he didn't think for one second it could be me. Stuff like that would happen and it was cool, but Lifter Puller struggled to break out beyond the local scene. And pretty soon, the band realized they'd probably gone as far as they were going to go. Lifter Puller breaks up and Craig Finn goes from being Craig Finn from Lifter Puller to just Craig Finn, ordinary person. He moves to New York. He gets a new day job doing the thing he said he wouldn't do. working on the business side of the music industry. He joins this tech startup. They're trying to stream concerts online in grainy, early-millennium-quality internet video.

21:52It was 2000. It was kind of his first internet boom. It was kind of that time where there was a lot of internet companies and no one knew how they were going to make money, but you ate cereal and sat in beanbag chairs. So I knew a lot of people that were doing gigs like that. I moved on a Friday and I started on a Monday, and I didn't have the job when I moved. He was 29 years old. He'd made peace with the idea that professional musician had just been a fun, youthful dream. Was he miserable? No, of course not. He was fine. A couple years passed. He told himself he'd still write songs, just for himself, just for fun.

22:28In fact, the story he started to tell himself was that maybe part of the problem with Lifter Puller, his final artistic endeavor, had just been that the fun of making music had been kind of ruined by ambition. So he and a few friends decide to start a new band With the explicit goal of not being successful Of not taking off Because he knows now that success Or the desire to have success Can be a kind of poison So they make some ground rules I mean it was comical what we were talking about One was that we weren't going to play any shows You didn't want to, why? Because I surmised, perhaps correctly That when you move the gear that's when the trouble starts.

23:10Wait, what does that mean? You know, like once you get like I mean, I think it was like okay, so you know, like when you lift or pull or you go out and you like you want to be in a rock band but you know, you start out your rock band and you end up learning a lot about your van because it breaks down a lot you know, and like suddenly like all your time is like auto repairs you know, and like well, this wasn't exactly what I imagined it. Once you get like move the gear and get it in a van and go play a show then that's when the fighting starts. Between the band. Yeah, so I was like, well, if we just drank beer on Tuesday nights and played, wouldn't that be the most fun part of it?

23:46And then, you know, no pressure. But of course, that wasn't going to work. The second someone asked us to play a show, we're like, okay, yeah, you know. This show, not a show exactly. This invitation for the least ambitious band in Brooklyn went thusly. Some guy had a comedy troupe. It's called Mr. Ass. Mr. Ass? Yeah, and they were doing this thing at Arlene Grocery, and they were like, do you want to do bumper music? Get a band together. Do bumper music. It'll be like, when we're changing sets, you'll play back in black. No singing. So I was like, yeah, that sounds fun. That's something to do.

24:21So we go and do that. And are they doing improv sketching? Yeah, yeah. So they're doing improv. A scene ends, and then you guys will play back in black. Yeah, and then they're like, you know. So we did that twice. And the second time they were like, hey, do you guys have any songs you could just warm up the crowd, play a song? And I showed the guys Knuckles, which ends up being the first Hold Steady song we ever had. I've been trying to get people to call me Freddie Knuckles. People keep calling me Right Set Fred. And it's hard to keep trying when half your friends are dying. It's hard to hold it steady when half your friends are dead already.

25:03And so we played that. And that was, I guess, the first Hold Steady show. But then after two of those, we were like, yeah, you know what was the most fun part about that is when we played our own song.

25:17Remember, they weren't going to be ambitious. They weren't going to turn this into a real thing. The trouble starts when you move the gear. But they were having fun. So they figured maybe they should just take the songs they were playing and record them. They made a demo. They kind of liked it. They made another. They realized, oh, you could sort of put these together. It would almost be like an album. We just combined them and called it a record. But it was really started with demos. And did it feel as easy? Like you're describing it as like not accidental, but just breezy. I think I knew that there was a power in keeping it light or something, you know, or keeping it, you know.