Regrets, I've Had a Slew

This is an iHeart Podcast. Guaranteed human. This is Jacob Goldstein. When you're a business owner interested in expanding to new markets, there's a lot to consider and countless questions to answer before making the call. The most important one being, are you ready? That's where ChatGPT comes in. Give it a goal, add your files, and ask Chat to help you map out different scenarios for the future of your business. So when growth is on the table, you've got an expansion plan ready to implement. Get started today at ChatGPT.com. Because every musician remembers the point where everything changed, and this podcast tells the stories that came before it. Listen to Before the Moment, a Lincoln Original series on the iHeartRadio app, YouTube, or wherever you get your podcasts. This is Jacob Goldstein from What's Your Problem? Running a business is hard enough. Don't make it harder with a dozen apps that don't talk to each other. 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And so you are wondering, what are the personal regrets of a man who traffics in the regrets of others? What might a man who receives to his inbox each day countless why didn't I's, what I should have's, and why did I eat that? A man for whom other people's regrets are the mud in which he ruts like a motherless sow. What might such a man's inner hellscape look like? Well, not to make this all about me, but since I do have a microphone and you are seated in chairs facing in my direction, I will say this. The reason I created a show like Heavyweight is because of my own capacity for regret. As a suckling baby, I'm certain I regretted choosing my mother's left breast over the right. As a teenager, I regretted things I had not even done yet. Alcohol, drugs, unprotected sex. I looked forward to regretting the hell out of them. And now as an adult, my regrets are still many. Take today, for instance. I regret the beta blockers I swallowed before coming out here. They're making me feel like I'm talking to you from the bottom of an oatmeal bowl. And of course, I regret agreeing to appear at On Air Fest in the first place. During that initial meeting with its organizers, I especially regret using words like awesome and sounds like fun. But the greatest breeding ground for my remorse has been sown in the gray garden of the heavyweight podcast itself. Sure, I've had some good times while making Heavyweight. There was my stay at an airport hotel in Burbank that served free cucumber water. And there was the time I used the recording studio after Esther Perel, and the whole room smelled of eggnog and gardenias. But nothing else comes to mind. Mostly the experience has been dominated by Dorkenschadenschmier, the German word for why must everything I do be the exactly wrong thing to do? Because of this tendency towards second-guessing myself, re-listening to my own work can be sheer misery. But is it not I, who knows better than anyone, that it is only by reliving, re-inhabiting, and re-flagellating oneself with the past that one can finally heal? If only I had my own Jonathan Goldstein. Alas, there can only be one. But for today, my on-air fest audience, you will be my Jonathan Goldstein to bear witness as, together, we will listen to my top seven most regrettable moments from heavyweight. Regret number one, seat of the pantsing it. Roused from a nap, fingers sticky with grape jelly, I'm often not at all prepared before an interview, but occasionally I'm so ill-equipped I should have my podcasting license revoked. In the clip of tape I'm about to play you, I'm phoning a 102-year-old woman with an 80-year-old regret and allowing this to happen. Hello? Hello, is this Barbara? No, this is Deborah. How are you related to Barbara? I don't know who Barbara is. The reason she doesn't know who Barbara is is because there is no Barbara. Oh, my, I'm so sorry. For some reason, I think I thought your name was Barbara. It's okay. I've lived long enough. I could take any name. I've listened to this over and over, and I still can't figure out how I came up with the name Barbara. My mother's middle name is Barbara, and my girlfriend in college was named Barbara, and her mother was named Deborah, so maybe that's why. Which leads me to regret number two, not keeping focus. When teasing out a story, I want details. You spilled hot coffee on yourself? Was there sugar in the coffee? What color was your coffee cup? Often this can elevate the storytelling, but just as often it can do the opposite. In the episode called Julia, Julia has only begun to lay out a painful memory from her private school days when I am already derailed by the details of her school uniform. That's sort of a puke green uniform with a button-down white shirt, and on Mondays we had to wear ties. We also had bloomers. I don't think I ever understood what bloomers were. It was just sort of like a balloon with holes in the bottom. And were they ruffled? See that? While it's true I've been cursed with a lifelong inability to distinguish between bloomers, culottes, pantalettes, pantaloons, drawers, and knickerbockers, should I have chosen that moment to sort it all out? Should it have required a five-minute digression and the sight of my producer frantically giving me the wrap-it-up motion to finally move on? This would be the part in the podcast where the music would swell up for a few seconds, allowing you to consider the question. Since I have no music, I'll instead give you a moment while I check my phone. Regret number three, being overly eager for resolution. If I've learned anything from my work in the business of forcing people to ask terrifying questions, it's that it's always best to just get it over with. Ask the question, why did you ruin my life? And get ready for a painful and often unsatisfying response. But sometimes, it's best to just get it over with. But sometimes, you have to take it slow. In Heavyweight's very first episode, my 80-year-old father, Buzz, had not spoken to his 85-year-old brother, Sheldon, in 40 years. In the tape I'm about to play you, they're just settling in with some small talk. My uncle Sheldon is sharing an anecdote, a filthy, inappropriate anecdote about someone named Johnny from their old neighborhood. Listen for my artful attempt to steer the conversation towards the touchy-feely, the. hokey-wokey, so soon into their first encounter in decades. We're riding on Queens Boulevard. Johnny's in the back seat with the who. He's got his naked ass up in the air. And he's humping. The funny thing is we had to stop for a light. And there's a truck driver sitting in the cab up high who looked at the car. It was funny. Have you guys missed each other? Have you missed each other? You know, he asks the weirdest questions. What is he, a broad? No, I mean, I don't know, it's, you know. A part of me still regrets not pile-driving my 85-year-old uncle Sheldon with enough force to set off his life-call medical alert bracelet. But instead I moved on. Regret number four. In the episode The Marshes, I regret comparing Steve Marsh to a dog. While it's easy to be free in your thoughts while writing a script, it can sometimes be hard to live with the aftermath. And in this case, the aftermath was especially hard because Steve and I became friends. And every time we get together, somewhere in the back of my mind is my guilt over how I described Steve in the episode, which is like this. I first met Steve Marsh at my brother-in-law's wedding. In conversation that night, Steve was given to making soulful observations, punctuated by the word man. It's perhaps also worth mentioning that while Steve wasn't invited to the wedding per se, all the guests were both happy and unsurprised to see him. Of course Steve would be there. And his entrance felt like a lovable St. Bernard had just wandered into the reception hall. Would you send a wedding invitation to a St. Bernard? Of course not. But would you be darn pleased to see one show up? Absolutely. I've always regretted comparing Steve to a St. Bernard. So I called him up to apologize. Hey. Steve? Yeah, man. What are you up to? So I'm giving this talk at On Air Fest. Yeah? So the thing that I'm doing, I'm talking about my own regrets while making a show about regret. Wow. But the reason why I'm phoning is because I've always felt some amount of regret for the way that I describe you in the marshes, the way that I. Really? Yeah. What part? The great Bernard? I always felt like maybe it was a little presumptuous to refer to you as a St. Bernard. I think I'm okay. But yeah, I don't know, man. I think you're good. I thought it was affectionate, Jonathan. It was. It was. It sounded affectionate. It sounded affectionate to me. Okay, cool. I think my brother had so much more trepidation about it. Not the way you described him, but just like bringing up the fact that he was a meth head, you know? Oh, shit. Yeah. One regret healed and another to take its place. I guess I owe Steve's brother a call now, too. And a great. A great swell of music to allow some time to properly savor the irony. And regret number five. Being unable to keep from gagging. While I always feel empathy for heavyweight subjects, I don't always show it enough. In the episode Tony, Tony is regretful about the fact that while he's been made a godfather three times, he's blown it each and every time with each and every one of his three godchildren. So I decided to help him fix those blown relationships. Here's Tony trying to reconnect with goddaughter number two, now a teenager, who he's not seen in years. We've just picked her up after school and are driving around. Knowing that young people enjoy gross stuff like poop-flavored jelly beans and Timothee Chalamet's mustache, Tony takes his shot at bonding. I have a really gross, disgusting story to tell you. Oh. Well, can you contextualize what disgusting is? Oh, my God. I'm only thinking about it because it happened right now. Oh, no, I don't like where this is going. Um, a friend of mine has been collecting his vomit for the past 20 years in a gigantic tin, like a gigantic metal drum in the basement. Oh, my God. What the heck? Instead of nearly retching, I should have been more supportive, offering Tony helpful follow-up questions to help keep the vibe light. I could have asked, did your friend buy this gigantic metal tub at the container store? And is there a special aisle for barf? And yet, on other occasions, I do worse than merely failing to support a subject. Which brings me to regret number six, disrespecting the profession of journalism by abandoning even the semblance of objectivity. In the episode Joey, a young rollerblading hipster named Joey is living in a loft with six other young hipsters. Since Joey is crippled by shyness, he spends all day in the office, all his days hiding in his room. But it isn't even really a room so much as it's an area in the living room walled off by a bedsheet. Eventually, Joey's roommates grew so upset by his creepy secretive ways that they kicked him out. Finding it hard to get a handle on Joey's essence, I decided to speak with his sister, Elise. She tells me about the phone call Joey made to her on the day he was ejected from the loft. He was, like, almost in tears telling me this story. And I was like, oh, my God. And he told me about how he cried, which is always. He doesn't cry that often. You could tell it was a big deal that he expressed that he cried about it. And he told the whole story, and I was laughing so hard because it's a really funny story, and I wanted him to see that it was funny, too. And he could see the humor in it, but he was also pretty clearly devastated. When I ask Elise what's so funny about her brother crying on the phone, she makes a pretty. pretty strong case, casually eviscerating Joey in the way only a loving sister can. Him in his rollerblades and often, like, funny-looking tank tops, his, like, creeper mustache and his mullet. And this is where I should have shown more professionalism, rather than laughing, which is what I did. Definitely just the look of him. Hang on a second. He has a mullet? Full mullet, full creepy young child mustache. And his shoulders and arms look. look strong, but they're small. And same with his legs. His legs are shockingly skinny. They do have an incredible shine to them, I will admit. I've always regretted my euphorically blithe tone, so I decided to call up Joey and comp to him. Let's do it. Is this Mr. Jonathan Goldstein? Joey, can I tell you why I was phoning? Please. So I'm talking about my personal regrets while making a show about regret. Okay, a little meta. So, you know, I played a passage from our story, your story, the Joey story. A regret that I had was when I spoke with your sister how I didn't maintain a lot of weight. How I didn't maintain a lot of journalistic objectivity. I ended up, you know, kind of laughing with her. Okay. I'm sorry you feel that way. You've always felt okay about it, I hope. That part, yeah. No, that was. Oh, okay. You say that part. Was there another part that you felt less okay about? No, I wouldn't say that. Done and done. Apologies made, grace granted. It really is that easy. And good luck with this talk. There's a chance I'll come. It's like down the street from my house, so I usually just sneak in. Oh, yeah. I'll leave a fire escape open for you. Would that be something you'd want to be like, and he's in the audience right now, kind of thing? I think if you were, yeah. I think I would do that. Okay. And, Joey? Are you in the audience? Hey! I'm so glad. Because I regret forgetting to leave the fire escape open. But you found your way in. Okay. Finally, regret number seven. I regret my regret. For me, no experience is complete until it's been thoroughly, vigorously regretted. But for some, regret isn't even a word in their vocabulary. In the episode titled Christina, Christina confronts her foster mother, Isabel, over a decision Isabel made 30 years earlier. It was a decision that derailed Christina's life for the worse. At the end of the episode, after a long, reconciliatory conversation, I brought up the notion of regret, asking Isabel, now in her 90s, if she at all regrets the decision that caused her foster daughter so much pain. This was Isabel's response. Oh, I wish I could. I wish I had known more about it at the time, I mean, I still have no regrets about it. It's as though Isabel just doesn't understand what the word regret means, so I offer a working definition. If we were to set off in a time machine where we could return to that time and Christina were to say, you know. I know what you're saying, but frankly, I don't know what I'd do. You know, I really don't. It would depend on what kind of a mood I'm in. If you were in the mood that you're in right now. I really have no idea. I could give you a lot of B.S. and tell you how good I would have been, but I wouldn't have been the truth. It's a decision that was made when she was younger. It wasn't the right one. But how many wrong decisions are made as we go along? Regretting something is a waste of time. You move on. Unsentimental, but correct. For me, regret has a mystical dimension, too. It isn't just about wishing I'd done things differently. Regret is a reminder of our free choice, even if it means freely making poor choices, because even bad choices speak to life's possibility that it's not just predetermined, that we're more than ball bearings repeating a mantra of, oh well, as we bump around in patterns set off by the Big Bang. Even though it often feels like we're so close to getting everything right, such a thing is, of course, never possible. The right way is outnumbered. Outnumbered a million to one by all the wrong ways. Nonetheless, we tell ourselves, live and learn. Maybe next time. Maybe next time, everything will line up just right. But until then, there's heavyweight wherever you get your podcast. Thank you. This is the part where Edith Piaf's Je Ne Regrette Rien was supposed to play me off, but we couldn't. So instead, I'll just say thank you and scamper off to the couch area for some Q&A with my producers, Kalila Holt and Stevie Lane. Thank you. And to get you started with the Q&A, Q, is it time for some advertisements? A, yes it is. If you're a music fan, here's a new podcast to check out. It's called Before the Moment, a new series hosted by the legendary Nile Rodgers. You know him as the producer, songwriter, guitarist, and co-founder of Chic. But in this series, he's hitting the road to sit down with some of today's most fascinating artists. From hitmakers like Miguel, to rising stars like Alex Warren, Nile explores the stories behind the careers, the songs, and the moments that changed everything. Because every artist can point to that turning point, that moment before the breakthrough, before the success, before everything changed. Through candid conversations and personal stories, you'll hear what happened before the moment that made them who they are today. before making any decisions. ChatGPT can help you prepare. 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It's sleek, handsome, and everywhere I go, I can instantly see who's part of the Whoop community. Whoop offers three membership tiers. Power your performance with the lowest price at Whoop One. Improve your health, now and for the future, with Whoop Peak, and tap into medical-grade health insights with Whoop Life. Whoop is a winner. New members can try Whoop with a 30-day free trial before committing to a membership. That's Whoop.com for your free month of Whoop. Here they come. C. Elaine, Kalila Hall. We were going to open the floor, hoping that maybe some of you might have some questions. Oh, yes. I would imagine that there are some stories that you spent a lot of time chasing down that ended up not panning out. So I'm curious, like, if you feel like you've gotten better at telling when something's not going to have a satisfying resolution, what the farthest you ever went, and then pulled the plug on something. I feel like there are certain kinds of stories that we've learned people are, like, more reticent to participate in, like, bully kinds of stories, when it's sort of, like, mean girl situations like that. Yeah. And then also, sometimes in the times where we do not find the thing that we're looking for, we really have to have something to say about it, and that can sometimes be very challenging, you know? Because if you don't find the parrot, then you have to be you know, like, well, who among us has not found the quote-unquote parrot? Maybe we're all parrots in some way. Yeah. And when you ask, like, what's the farthest we've gotten, of course things have fallen apart. Like, we've located the person, and they're dead. You know, like, that falls apart. But we usually just, like, shelf the story and keep checking in with the person, and sometimes, like, with time, something new comes up, or something changes. Anybody else? Yes, in the back. We were considering having Joey zipping around on his rollerblades with the microphone. My question is for the producers. I believe you guys have been with the show for a super long time at this point, right? Yeah. How has your, how has the experience and role of producing the show grown and changed? Like, are you able to work together in person, or is it remotely? Well, I'll answer the remote thing, because that's, like, an easier thing. Like, that's just facts. Me and Stevie are both in New York. Jonathan is in Minnesota. So we're doing a lot remotely. But occasionally, we're in the same place. And often, like, Jonathan and I just went on a reporting trip. So, like, sometimes when we're in the field, we're also together. But a lot of the editing is remote. How has it changed over time for us? I think we've, like, developed a shorthand. Yeah, like submarine talk. Yeah. Like, abbreviated language. Yeah. And also, it's, I think, the loss of my brain. I just, like, point to things, and I'm like, you know, that thing. I still remember when you called George Clooney the gray-haired doctor from ER. But you knew what I was talking about. And I knew who you were talking about, yeah. Yeah, see, that's teamwork. Yeah. Right behind Sean Cole. Because the stories that you are looking into for these guests are so um, excuse me, my voice is so hoarse. Because they're so personal, and often these stories that people have been carrying for their entire lives, I would imagine that the work you do is changing some lives. Have there been any stories that you feel have changed your life, either in hearing them or the process of spending years working on them? Hmm. Nah. Ha, ha, ha, ha, ha, ha, ha. I, I, my life has changed all the time, I will say, in all sincerity. Um, like, there's so many people that I admire that we, that have been subjects on the show, and I'm like, what a, like, special, unique person, you know, to lend themselves to this thing, and, yeah. Yeah, and I feel genuinely humbled that people are willing to share that with us, and, like, invite us in on that process. Yeah. For me, it's maybe not, like, one particular story, but a big lesson that I've taken from it is, like, when you have something in your life that you feel really terrible about, not always, but, like, most of the time, you are thinking about it more than the other person. And it's just a nice thing to remember in your own life for the things that you feel, like, you've done wrong, that, like, probably the ripple effect is not as big as you maybe thought it was. And that if you feel weird about something, you can be like, hey, what was up with that? Like, you can ask people questions about stuff, and they can not really answer you, but you can at least try. And you can record the whole thing secretly for potential broadcast. Depending on the state. She's kidding. That would be highly unethical. I'd love to ask about Jackie. I think it does something pretty special and i would just love to hear about how it happened and how you've thought about it going forward can we turn up the house lights jacket there's no way she would be ever uh well how did it come about it was just like a last minute thing um we had a very elaborate opening very conceptual involved me on the g train and the voice of the stand clear of the closing door voice i had a friend who sounded just like that guy and he was like the voice of god and we would have a conversation at the beginning and at the end of the show it was a whole it was like producing a whole other and you can hear it if you sign up for pushkin plus yeah i tell the story yeah uh but then at last minute i was like i could just call up my friend jackie who will just be annoyed and hang up and it'll be entertaining and that was that was it and she and i've been ever since ever since but i've no i've known her since we're children you know and the dynamic's been pretty much set um as a fellow producer sometimes it feels like you listen to the tape about a hundred times um with those particularly hard-hitting episodes i'm wondering like over the years has it gotten easier to listen to those really difficult stories or how's like how do you deal with the emotional exhaustion that can come from that while you're making it you mean yeah i i feel like i mean like we're all unwell kalila is right we are all deeply unwell but maintaining this level of emotional instability doesn't come cheap we'll be right back after these paid messages from our sponsors with our emotional instability now fully paid for by our corporate sponsors we return to the question of how the team copes with the heavy stuff here's stevie i don't know if this is good or bad but i find that for me personally like when i'm like making making it and listening to it over and over and cutting it and like writing it before i've played it for anybody like it starts to kind of lose its power and i don't hear it in that emotional way i don't know if it's good or bad in a way and then it's like not until i'm playing it in an edit for other people that i feel like i really hear it that way again i don't know if that's like a self-protective thing my brain is doing but like i've never i've never cried like cutting the tape but i will like cry in an edit sometimes it's once that scoring music's in there yeah yeah yeah yeah i think you're right though stevie like while you're actually cutting and writing you're like so sort of hyper focused that you don't have that like i feel like i in the interviews have a lot of feelings about that feelings about stuff and then when the episode is done and in between it's like i'm so sort of like tunnel vision on making the thing that i don't know that also feels but yeah it feels like i'm like desensitized to people's problem solving it's like you're yeah you know it's like you're putting together a crossword puzzle a little bit yeah totally yeah um why do you think people agree to talk to you especially people who are you know from your initial email with them it's clear that like maybe they have something to answer for they're maybe going to be the antagonist in the story why do they say yes i wonder that all the time i wonder that same thing but i just think like people aren't used to having people like ask them questions and then sit there and really listen like really listen yeah i think also not always because sometimes yeah people just don't remember or but um like the the one me and the trip that we just took the reporting trip i feel like in that case and in some other cases too like maybe the person we're going to also has unresolved feelings about it or like regrets so in some ways even if they did something wrong it's like helpful for them to have that space as well and also like we when someone is really willing to like sit down and have a conversation with us like that we don't want to cast them as just like a villain you know we like want to give people the chance to talk to them and we don't want to cast them as just like the chance to like give their perspective and say their piece too but also a lot of people say no and then those stories don't happen so yeah the best episodes are the ones where there's like a reciprocity where both parties are getting something out of it but um uh there there is um there is a leap of faith i think because there's not they're not like performer type people they're trusting us so um i think it's probably mostly for jonathan uh there have been some episodes where it sounds like the subject is sort of hesitating confronting the person they're trying to maybe reconcile with and there have been times where it sounds like you have to step in um you strike me as somebody who's perhaps non-confrontational so i'm wondering what do you do to get yourself to confront them i think i think about what it's going to feel like if i don't do it and i don't always do it or i don't always do it so well but i think about what it's going to feel like and i don't want to live with that echoing through the years of having let the person down you know um so i usually try to like awkwardly work my way through it i don't think i have a special skill set i just think like i'm there you know uh in the the i always mispronounce this the deus ex mac machina machine you know like where i'm just descending and i'm wearing the toga and the beard and like i have to play that role you know so i do my best is some of it too like the crossword puzzle thing where you're like you're able to take the emotional part out of it because you're like i need this for the episode so i have to ask there's that also yeah i like i can't i can't i can't face you two without having actually just done it big fan of the show so it's fun seeing you guys um i'm curious from to hear from all of you on this between in the layoff between spotify and pushkin what was that like for you guys personally and did you think the show might not come back i was really down like unexpectedly like it was very difficult for me in a way that i did not anticipate i i felt like oh this isn't so bad you know i'll catch up on my reading i'll take my son to school and stuff like that but like pretty soon i don't know if you were aware of just what yeah yeah you were aware i was really like not in not in good shape yeah so thank you pushkin yeah and look at him now it was like a real up and down i would say for me i agree i do think the we've talked about this a little bit but the person like the taking the step back actually was helpful like i feel like it then once we were set up again helped us like come back with like renewed energy and new like joy and do doing this thing i remember like one of the first um like story meetings we started having when we were looking back at pitches that had come in in that year um jonathan was just like yeah let's do that one yeah let's do that one and kaylee and i were like who is this so open i'm not normally like that what's next book them mr optimism all right are we out of time the clock's at zero no the clock's at zero thank you thank you so much thank you heavyweight is produced by senior producer kalila holt and supervising producer stevie lane today's live show was made possible by sarah bruguere phoebe flanagan and morgan ratner mixing by emma monger with production help from lisa wang we'll be back next week with a brand new episode if you love music and great artist interviews check out before the moment hosted by nile rogers this new series follows nile as he travels across the country talking with some of today's most fascinating artists about the moments that shape their lives and careers from hit makers like miguel to rising stars like alex warren nile explores the stories behind the careers the songs and the moments that changed everything because every musician remembers the point where everything changed and this podcast tells the stories that came before it listen to before the moment a lincoln original series on the iheart radio app youtube or wherever you get your podcasts for i don't know how long maybe 12 13 years i've worn a whoop band on my wrist i started doing it because i met the founder of whoop at a conference he heard that i was a runner and he said oh you'll love this it's perfect for athletes and he was right i've worn one ever since every time i work out i see how hard i worked how long i need to recover i wake up in the morning and i get a complete picture of how my sleep went which helps It helps me understand the kinds of things that lead to a bad night, and the kinds of things that lead to a good night. It's sleek, long-lasting battery, and now with AI looking at all my numbers and coaching me. Whoop is a winner. CRM, accounting, inventory, e-commerce, HR, fully integrated, easy to use, and built to grow with your business. Why not you? That's odoo.com. Guaranteed human.