Does anyone actually like their job? (classic)

0:00Hello! This week we're rebroadcasting one of our favorite episodes. it's about a question that actually haunted me for most of my 20s. Does anyone actually like their job? One of Search Engine's pet obsessions, you may have noticed, is work. And this episode was the first time we took a swing at that pinata. This year, we're starting the practice of periodically rebroadcasting some of our favorite episodes, at least on the main feed. Our incognito mode, which you can sign up for at searchengine.show, does not air rebroadcasts. But honestly, I'm pretty happy to play this one for you again. Listening this week to it again for the first time since we aired it in 2023, I remembered that for me, I'm constantly on this strange wheel of samsara with work, loving it, feeling pummeled by it, wondering if I'll ever find some kind of balance, or if that balance is even a real thing.

0:51And I found that our silly question and our exploration of its answers had actually given me some guidance, some notes towards some kind of solution. Anyway, please enjoy the story after these ads. This episode is brought to you in part by Quince. As the air turns crisp and the leaves start to change, I am thinking about layering pieces that feel cozy but still look put together. And Quince is where I'm looking. They have 100 % Mongolian cashmere sweaters, which are unbelievably soft and warm, perfect for layering under jackets or over a shirt. And they start at just$60. I've been also eyeing their denim.

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3:40When 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.

4:20From 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.

5:0124-7 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.

5:48But 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,

6:06I 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.

6:33They 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 sweat and wet confetti. If you want to get a little bit light in the headie, it's gonna have to get a little bit heavy. The songs I thought were perfect. Stories 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.

7:13I got very obsessed with the band. And 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. And 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.

7:54In 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.

8:30Man, I say the same thing almost every night. 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. And 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.

9:16And 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. For 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.

10:00I 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. In 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.

10:36Questions about ambition, questions about jobs, questions about how to survive as a person.

10:44So after the break, Craig Finn.

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13:05Welcome 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-E-Y I was listening to bands. to Bay City Rollers and Kiss and getting really enthused about music and also the monkeys who are on TV.

14:01It looked like that was the best job, you know? 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. Like, the whole thing looked pretty great. And I was a very mild-mannered, nerdy kid, so, like, it was not, 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 till I asked for an electric guitar. And what did your parents do? Oh, my dad worked for Ernst & Young, an accounting firm. And my mom was a homemaker since I was born.

14:38So they were not rock and roll people, but they were very supportive. And 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 hurts. Did you feel that way towards music?

15:10Yeah, I mean, one thing I can point to is in college, I went to Boston College, and I was writing for the school newspaper. I was reviewing records. And that was, you know, I did that and maybe I did okay at it, but like I got the feeling that that wasn't the side of it I wanted to be on. Yeah. 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.

15:59This 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.

16:19In the video, Craig Vinn 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.

16:38I 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. But I do feel like I can already hear some of what Craig Finn is going to do really well in his 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.

17:17People 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.

17:51So 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. Yeah. It was really kind of an interesting, spectacular place. I started out in the annuities department and people would call in and you tell them your balance and you do small transactions for them.

18:31You know, I'd wear a headset mic and there'd be, it'd be like this like 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, um, 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 yeah you know um i remember there were these guys that i'd hang out with sometimes and they would they would cut they were like go out almost every night and then they'd come in and they'd rate their hangovers and they would like uh and you had we had like an intranet system you know like um 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 um so that's so such a low number yeah i mean and it's funny the thing was is there'd be a tax season um 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.

19:38They'd be really angry when they got you. And so I remember during that period each year, not wanting to go to work, like 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 it's a regulatory thing.

20:20And a lot of people had problems passing that exam. And 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 going to 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 where i'm now a hiring manager trying to figure out if craig finn would be a good fit synergy wise for my team?

21:02Series seven 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 sevens 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. 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. It was like an insurance policy that was supporting. Yeah, it was exactly that.

21:40And 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 was, 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? But 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.

22:24When 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. And 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.

22:59And 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. It was 2000. It was kind of his first Internet boom. And 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.

23:39So 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. In 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.