LIFTOFF: The Art & Science of Conversation

9. WHEN: It's Time to End

• Ilana Gilovich • Season 1 • Episode 9

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LIFTOFF: The Art & Science of Conversation
Episode 9

In Episode 9, host Ilana Gilovich learns how to navigate conversational endings gracefully.

Featured Guests:

Transcripts for all LIFTOFF episodes are available on Buzzsprout.

ILANA GILOVICH: [00:00:00] In this last episode of Liftoff, we're finally grappling with the when of conversation by talking about endings. In this episode, we'll learn why we have such trouble ending conversations. We'll learn several tactics for ending conversations so we can conclude them on our own terms. We'll also learn why endings are less scary than we might think.

Conversational conclusions can feel weird. So I asked others for tips on how to elegantly end a conversation. Some guests had very specific tactics. Here's my dad, Tom Gilovich. 

TOM GILOVICH: One of the fears people have about conversations, they don't know how to end them. Uh, and that, you know, you're often taught, oh, what are some icebreakers that, you know, can get it going?

That's great. But we also need to give people advice about how to end them. Uh, you know, Nick Epley talks about these as ice makers, how to, how to end the whole thing. Uh, what are some ice maker advice, uh, that you could give. [00:01:00] And here. I've just stolen a technique that, uh, the great Amos Tversky used, and this works really well in, you know, mentoring meetings, but it applies broadly too, that Amos would often end our meetings by saying, I.

To be continued. You can't, you can't believe how often I've used that one. Uh, and it, it works because it's clear that the conversation is over, but it also expresses an intra that, Hey, this went well. It's worth continuing, it's worth continuing with you. So it's both cold and warm at the same time. It ends the conversation and it makes the person you're talking with.

Feel valued, it meets the Maya Angelou criterion. Uh, I think it's brilliant and, uh, maybe I've overused it, but, uh, I, I haven't seen any evidence of that. I've used it, uh, a lot. In fact, today in class [00:02:00] one student said, you can't, after you said that thing about tversky's to be continued, you can't believe how many times I've said that last, last week, and it worked really well.

Here's Alison Wood Brooks. 

ALISON WOOD BROOKS: Everything about conversation is a coordination conundrum. Like what are we gonna talk about? How long are we gonna talk about it? How are we gonna do it in a serious way? Are we gonna be silly? And the end of the conversation is the final coordination decision, right? Like it's the final one.

You both decide, okay, we're gonna be quiet and we're gonna walk away from each other, or we're gonna hit leave on the zoom window, 

right? 

Um, and so it's a coordination conundrum and just knowing. That final choice is a really hard thing to coordinate. I find Very freeing. 

Cause you realize, oh, this is like really hard for everyone.

We're not gonna get it perfectly right. Most of the time, just like all topics that people talk about, we stay too long. If it went well, both of you're gonna be so excited to connect again. And [00:03:00] maybe it's tomorrow, maybe it's in five years. If it went well, you're gonna be so glad to see them again. And, and ending it doesn't, isn't the end of, of everything.

Every relationship is this repeated sequence of conversations over time. So ending that conversation is just like, oh, when will we get to connect again? 

ILANA GILOVICH: Here's Mallory 

MALLORY GRACENIN: I am still working on the right ways of navigating, uh, how to gracefully exit a conversation. Um, when someone is a bit, uh. You know, enthusiastic, but I realize we've been talking for 20, 30, 40 minutes past the time that maybe I need to go home from work.

Yeah. And relax 

and unwind. And so the same things that you look for that you don't want in a conversation, you can begin to actually, I. Consciously or unconsciously, you, your body might start doing it Mm-Hmm. And start to give those Qs. You might cross your arms. 

Yes. You 

might look around a room just for a moment or two.

Um, you might check your watch. Um, those things I think naturally start to [00:04:00] happen. It's really important to set, uh, a good amount of healthy boundaries on who gets to take your time and for how long. 

Mm-Hmm. And so. 

I found it to be incredibly, it's a a bit more blunt, 

yes. But 

I will put my hand on their shoulder gently, give it a squeeze, give them a real, really nice smile, whoever I'm speaking with, that I need to end the conversation and I go, you know, I'm gonna go have a drink with my friends over there, but it was really nice talking to you.

Mm. 

Or I'm gonna head home for the night. Or you know, I have to say, I have to work the room a bit. I have more friends to see. Uh, but it was great talking to you. Mm-Hmm. And if they're really not getting the hint, um, and you find you're in several situations where you don't really know how to exit, I find that's more of a you problem than it is 

uhhuh.

Um, the other person's problem. You have to find a, you have to find a healthy, clear way of not feeling guilty of taking your time back. 

[00:05:00] Hmm. 

And finding your way out of the situation. So I think it's with, to me, exiting is nice. With a gentle touch. Yeah. A squeeze, a hug. Uh, Hey, I, I wish I could stay and talk all night.

I can't. But it was so good seeing you. 

Mm. 

And that's that 

ILANA GILOVICH: Other guests were more comfortable with abrupt endings. Here's Tessa Velazquez. 

TESSA VELAZQUEZ: I have a policy too, like you don't even have to say goodbye to me. Like Irish exits are welcome. Like just leave. If you don't feel, if you're like done and you're tired and it's Monday and you don't feel like talking anymore, go like, I love that for you.

You know? Like just to take the structure out of it, I hope gives people permission. 

ILANA GILOVICH: Here's Max Stossel. 

MAX STOSSEL: Yeah, my friend Rob, who we talk on the phone a lot, one thing I do, uh, with him and he enjoys 'cause it also gets him permission to do the same, is like, just pretty abruptly being like, alright, this feels over.

Bye. Um, and then just like, we can do that with each other of [00:06:00] this instant sort of abrupt, all right, we're hanging up. Cool. Yeah. Great. Yeah. Um, and which just sort of playfully cuts through the like. So like, when are we talking again? What's the, which also inherently has the trust in his and my relationship.

Like they'll be next time if we need to call each other, we will. And like that's, that's known. Um, and. Um, but yeah, like I do believe endings are lies. Like I think things don't end, they change. And so like, yeah. What is, what is an ending and what is an ending of like a, of a podcast? I like, I don't know exactly what's that.

It would've been, I kind of wanna just hang up like just in the middle of that sentence. That would've been kind of. Cool. But I don't know what your process is and especially as I have already, uh, once pushed on the structure and format, I don't want to do that. And I would like to resign to whatever is more comfortable for you, but it would've felt cool to, in the middle of that sentence, just end the podcast.

ILANA GILOVICH: Okay. Cool. This conversation feels over. I'm gonna hang up. [00:07:00] 

MAX STOSSEL: Alright, bye. 

ILANA GILOVICH: Bye. 

For this last episode of Liftoff, I interviewed Adam Mastroianni, an experimental psychologist and author of the popular science blog, experimental history. Adam earned his PhD in psychology from Harvard in 2021. He also does improv and standup comedy, and has escaped from over 150 escape rooms.

Fittingly, Adam has conducted some well cited research on conversational endings. Specifically, he found that conversations rarely end when we actually want them to. That we tend to either overestimate or underestimate the amount of time our conversational partners would like to spend talking. As you'll hear, Adam is a warm, witty, and wise conversationalist.

So Adam, you are an experimental psychologist. You run an incredible substack called Experimental History, and I think I would [00:08:00] like to propose opening this podcast with a cheeky experiment, which is sure. We each decide we're going to just declare when we feel the conversation should be over. No hard feelings.

We'll just put it out there and then we can assess whether that matches up with our internal sure estimations of, of where we think the the conversation should have ended. 

ADAM MASTROIANNI: Yeah, you know, I wanted to run this study, uh, like seven years ago, and eventually we decided there's no way to do it. That no one will be brave enough.

I literally had purchased, we wanted to bring people into the lab and give them, uh, you, you can buy like a mouse for your, for your foot. So some people use these for like annotation. Um, or, or whatever you might need. Like you need both hands on the keyboard and you'd wanna click with your foot. Yeah. And we thought, okay, we're gonna put a mouse on the floor and put each person's foot on top of their own mouse, and you click it when you're ready to go.

Uh, and so, but I, I, for one thing, couldn't find a mouse that didn't, wasn't audible. So two people would be talk, talking and with a mouse, like this would be like, [00:09:00] and uh, so you have any cousins, he'd hear like, click, click, uh, so it didn't, we never ran it, um, because I thought no one would, would be brave enough and I certainly am not.

So, um, I'm here until you say, go. 

ILANA GILOVICH: The reason we're talking about why conversations end is because Adam has done some fantastic research on conversations never end when both parties or either party wants them to. So I know you're probably asked this all the time, but I would love for you to talk about that research.

And I would also love you to talk about if at all that research relates to your fascination with escape rooms, because that feels like you love a good out, and I would love to talk about that. 

ADAM MASTROIANNI: Yeah. Yeah. So the, the, uh, the, the study was um, basically we bring people into the lab and we tell them, talk for as long as you like, um, and just let us know when you're ready to move on to the next part of the study.

And then we shut the door and they start talking and, uh, and unless they, they go until the end of [00:10:00] the hour. Like we only have them for an hour. So unless they went all the way, which by the way, a third of participants did, but for those who didn't, they, they get out and they say, okay, we're ready. And then we ask them.

Was there any point in that conversation when you felt ready for it to end? 

Yeah. And if they 

say yes, we ask like, okay, can you estimate when that was, like how many minutes ago, basically? And if there wasn't a point where you felt ready for it to end, how many more minutes did you want to go? And what we found was that virtually nobody says it ended when I wanted it to end.

And, and, uh, and even fewer groups and fewer groups do, um, both people say it ended when they wanted it to end. That was like 2% of our whole sample. Wow. Um, and we think this happens for two reasons. One is people very rarely want to go for go on for the same amount of time. So if I wanna talk for 10 minutes and you wanna talk for 15 minutes, we can't both get what we want.

And the other is people really don't know when the other person wants to stop talking. So if I would like to end at somewhere between when I want to end and when you wanna end. I can't do it 'cause I don't know when that is. Uh, so when we asked people to guess how, uh, when [00:11:00] the other person wanted to go, they were off by about half of the length of their conversation, which was also about the difference between what they wanted in terms of conversation length than what they got.

So these, these also weren't small in terms of the conversation. We're talking about half of the length. Both we're getting half more or less than we wanted. And when, I guess when you want to go, I'm off by about half of the length of what we talked. So we talked for 10 minutes. I'm off by five. Um, how this relates to escape rooms.

Uh, I mean, the nice thing about an escape room is you're in there for an hour and if you don't or otherwise you're done. Um, and, uh, and often you don't have to, you know, you're trying to solve puzzles. You, you, you have a goal in mind. So there's a reason to talk to it to other people. And when that reason is done, you stop.

Um, I did, uh, so part, part of this research that I've done is, um, that wasn't the, the focus of the study, but one, one ancillary finding we found is, is that when you describe this to people and say, okay, how much do you think people are gonna enjoy themselves in this study? People go, not at all. These, these are gonna end very [00:12:00] soon because people are gonna have such a terrible time.

And in fact, we finally, people actually have a pretty good time on average. Um, mm-Hmm. I mean, one thing, you know, they, some of them, a third of them talked for an hour to a stranger. Most people didn't think that could happen. And so when I was kind of hopped up on this research, uh, I wrote an article about this, uh, that that's in the Atlantic where I uh, I was like, okay, I had an extra day in Atlanta after a conference and I was like, let me do, let's do some escape rooms with strangers.

'cause it's fun to meet strangers according to research. Let's do it. And it was the worst day I've ever had. I did this twice. They just ruined two different birthday parties. I showed up and they were like some 30 somethings who were like. We never get to spend enough time together. Let's get a babysitter and like go to the, go to an escape room.

And then I'm there being like, Hey guys, what? What's up? And I was really bad. Uh, and they didn't, they were very polite, but they really didn't want me there. Um, 

ILANA GILOVICH: wow. And so there wasn't any banding together in the name of a greater cause. It was really just stuck together and unpleasant the whole time.

ADAM MASTROIANNI: They banded together against me. So I think I [00:13:00] maybe made them better off at the expense of me. I imagine that when they get together, they might go like, here, remember that weird guy who showed up to our escape room? Can you believe it? Just like to see, see what, how, where I am now. 

ILANA GILOVICH: People love, I made it, you know, a common enemy, a common nemesis.

ADAM MASTROIANNI: Exactly, and I'm willing to play that role for them. 

ILANA GILOVICH: That's really magnanimous of you. That's great. So in, in the research, does it usually swing, people want the conversations to be shorter, people want the conversations to be longer or a mix of both? 

ADAM MASTROIANNI: Yeah. This is a great question and, uh, there's like three levels on which you can answer it.

So if you want. So, uh, if you look just at, did people say they wanted to go sooner or not? Um, a majority of people say there was a point at which they wanted the conversation to end, and it was sooner than it did end. So if you just look at that, you go, okay, usually, at least in our study anyway, people wanna go sooner.

But then if you look at, okay, well, well, how much sooner did they on average want to go? Sooner or later? 'cause they could report how many minutes before or how many minutes [00:14:00] after. If you average those two together, you actually get pretty close to zero mm. But then if you ask, well, saying that you wanted to go sooner, that's bounded at zero.

So I can't say that I wanted to go before the conversation began. Uh, even if it's really bad, I can only have zero minutes. Um, but I can tell you that I wanted to talk for up to an hour longer that we, we let them say, say that. So the one of these is bounded, the other isn't. And so it's weird to average them.

And the other problem is. One of these is, um, retrospective about something that happened, and the other is a guess at what might happen if we keep talking that I can say, oh, I want to talk for 10 more minutes, but it might turn out that, that actually I want to go after five, or I don't want to go until 20.

So these numbers are really hard to put together into a reasonable number. I think the, uh, the way to answer this question is most of the time in our studies, people wanted to go sooner. Um, but they didn't necessarily spend most of their time wanting to go sooner. They, uh, in terms of the amount of time that they wanted, they wanted just as much more as they [00:15:00] wanted less.

And when I tell people about this or, uh, I did a bunch of like, interviews with journalists when this paper came out. Some of 'em straight up told me they were like. Yeah, I'm gonna write the story about that people wanted to go sooner. Um, and I'm like, well, okay. Yes, but actually, you know, 20% of our participants reported they didn't want the conversation to end.

Uh, and I just think people have such a schema that like, oh, conversations are such a drag. I always wanna get out. Um, that that's the result that they're looking for. And we did find that, we found plenty of that, but we also found a good amount of the opposite. 

ILANA GILOVICH: Wow. This is fascinating and I, I'm curious of qualitatively, I don't even know how you would measure this, but.

Do you feel like some of the participants were better conversationalists than others and that the people who wanted it to be longer were poor conversationalists? The people that wanted it shorter were exhausted. Adept, conversationalists? 

ADAM MASTROIANNI: Yeah. Yeah. Some, um, you know, I don't know if they've, uh, ever published this, so maybe it didn't turn out.

Uh, but I, I, some friends of mine once told me that, that, um, they. [00:16:00] Survey the whole dorm, um, at their college and ask people to nominate the best conversationalists and the worst conversationalists in the dorm. And at least what they told me at the time when this was in progress, they were like, most people end up on both lists.

ILANA GILOVICH: A brief aside, the research that Adam mentions here is actually my dad's research. After we stopped recording, Adam revealed that he wasn't sure whether or not I would want him to explicitly mention my dad. I revealed that the description of that research had sounded like my dad's, but I didn't wanna ask in case I sounded arrogant or misinformed.

I. I mention all of this because I think it exemplifies perfectly the silent subtext that each conversationalist conducts in their head out of politeness or anxiety. Our exchange is a good reminder that if you're having a moment of hesitation or puzzlement, it's probably okay to name it because your conversational partner might be experiencing one too.

ADAM MASTROIANNI: I should really follow up with them to see if they, yeah. Uh, if, if that was, that was true, but it, it felt like it rings true [00:17:00] because. Watching these conversations. First of all, they all looked pretty bad to me. From the outside. Yeah. But then, but I think conversations look bad when you're not in them because people are like, so like, where do you live?

And I'm like, oh, this is pretty bad. But, but I think when you're in it, it feels different, like you're trying to make it work. Um, and they were conversations, so we recorded them and that I watched back and I'm like, this one seems really bad. But they would talk for the whole time and afterward they'd be like, yeah, that was pretty good.

Wow. People exchanged numbers afterward. Um, and it wasn't the people who looked great at doing it, um, always, anyway, anyway, um, so yeah, I, I didn't, I didn't feel like I picked up a sense of like, what made some work better than others. 

ILANA GILOVICH: Wow. I. So I'm assuming that you got into this research either because you were always being trapped in conversations and you really wanted them to end, or you were just yearning for them to go on longer with your escape room, comrade say so, yeah.

On either end of the spectrum, what was the genesis for this [00:18:00] research? 

ADAM MASTROIANNI: Yeah. Um. So it, it sort of began, I, I was at uh, Oxford before I started my PhD and I was um, getting ready for a party one night and putting on my bow tie. 'cause all parties at Oxford are black tie. It's very annoying. Oh wow. I felt like I don't wanna go to this party 'cause I know that there's gonna be this inevitable time when I don't, I'm done talking to the person I'm talking to.

I wanna go talk to someone else. But there's no graceful way of pulling off that maneuver. There's only so many times you can refill your drink or excuse yourself to go to the bathroom. Right. The go-to I got to thinking yes. And I got to thinking, well, what makes, what makes me think I'm so special? How do I know the other person didn't want to go before me?

And they're just pretending to that they want to keep going because they think I wanna keep going. They're being polite, but I'm doing that because I think they're, they really wanna keep going. And so that's why when I started talking about this with my advisory, I ran these studies with, we thought that that was what would happen on average.

And it, it is kind of what happens on average, but it's not what happens all the time. Um, the, the most common outcome was both people wanted to go, uh, before they actually did. Um, but there were many other [00:19:00] outcomes. Um, but yeah, that, that's kind of where it came from. 

ILANA GILOVICH: Oh, cool. And what are the kinds of conversations I.

That you love to have, because even thinking about the, the unborn study that you mentioned in the dorm room, I actually, once you say it, it feels counterintuitive, but once you say it, I can imagine that the So-called great conversationalists could be very polarizing. They either ask lots of questions.

Some people love that, some people don't. Yeah, they're very humorous. Some people love that, some people don't. So what are the different ingredients of conversations that you personally love having? Yeah, 

ADAM MASTROIANNI: yeah. Um, I love a conversation where, um. People are following the principles of improv, whether they're they're improvisers or not.

Um, one of my, one of my improv friends put it this way, that, that, uh, that the thing about an improviser is when you shoot them, they die. Um, and you mean this in a violent way, but like, if you enter a room and mime shooting an arrow, let's say an arrow rather than a gun at Thank you, add another improviser.

They will clutch their chests and they will like fall over dramatically. Right? Like [00:20:00] they will act like the arrow exists, just like you acted like the arrow exists. And, and in a conversation you don't literally have to be, you know, miming or playing charades, but you do that conversationally. Um, yeah.

Where like I throw out a gambit and you can choose to be like, that's weird. I don't like it, I don't engage. Or you can, you respond and you can play the game. Um, and, uh, and so I have fr Freds, my wife in other room, my wife included, were like, uh, I could walk in that room and be, and be like, what's up Odium?

And she could be like, what's up Jeffrey Tambo? And we'd be like, we're playing a game now. Like, it's fine. Um, but other people would be like, why are you doing that? That's weird. Um, and I'm like, you just drove this car directly into the side of a mountain. And like I said, I want to get out. Uh, yeah. 

ILANA GILOVICH: I love that.

I love the idea of a game, the idea of keeping the ball in the air and kind of keeping this kinetic energy going. Um, and that's a great segue to talk about your experience in standup comedy and improv [00:21:00] comedy. So how has that informed you? You articulated this already a little bit, but how has that informed how you think about conversation?

ADAM MASTROIANNI: Yeah. Um, yeah, I wrote the, I wrote this piece called, uh, good Conversations of a lot, have a lot of doorknobs. Um, it was based on this experience that I had in improv, we talk a lot about taking focus. Um, so, uh, this happens all the time, but especially when you're doing musical improv where I. Uh, you know, improvising a melody in lyrics is difficult.

You can only do it for a little bit before you run out of steam. Yeah. And the way to make a song with other people is that everyone's always looking for the point at which you've lo like, you're gonna lose steam soon. And I'm gonna jump in when, uh, before that happens for you. Rather than thinking about give and take a focus where I have the spotlight and then I, I hand it over to you.

I'm in the spotlight doing my thing, and you take it from me as an act of kindness. Ah. And so usually we think of, of taking is like, well, we all wanna be in the spotlight, so we should, you know, seed it to other people. Um, and that's [00:22:00] the polite thing to do. But when you're doing something difficult, the polite thing to do is actually to take it.

Um, and this made me think of, uh, basically two different models that people have for approaching conversations that some people approach them as, uh, givers. That, um, like, I'm gonna ask you questions and I'm going to create opportunities for you to speak. And some approach it as takers that, uh, I, I'm going to, to like grab the spotlight from you.

Um, and, and I think a lot of people, especially givers think that like taking is selfish. That like, no, you should give, you should ask questions. 

Um, and, and I think a lot of times yes, that is true. But that's not the only way to be generous in a conversation. Um, that, that sometimes you want the other person to do some of the poll.

Like I don't wanna ask every question. I, every question I ask is really an opportunity for the other person to do something interesting. Um, and so when, when two takers get together, it's fine because like I say my thing and you say your thing, when two givers get together, it's also okay.

'cause you're both fighting to ask each other as many questions as you can. But with a giver and a [00:23:00] taker, you know, the giver gives and the taker takes, and the giver goes like, what? What gives not you? You're not giving to me. And the taker's like, man, this person's not taking anything. They're not pulling their weight.

Um, and so I think some of this conversational mismatch is people, you know, not being generous enough with one another. But I think a big part of it, an unseen part of it is people not understanding the way that other people are generous in conversations. Um, that that's one way that, that, uh, improvise has changed how I think about conversation.

You guys think about this a lot, having conversations with people. 

ILANA GILOVICH: I also loved that you defined the word affordances. In a simple demystified way, because coming out of academia, everything is an affordance, and I'm not ever totally sure what that means, 

but in conversation, you put it in very pragmatic, utilitarian terms, and you talk about an affordance as a doorknob or a foothold that we're creating in conversation.

It doesn't have to be a question. It doesn't have to be a statement. But it's something, as you say, for one of [00:24:00] us to hold onto to further this endeavor that we're embarking on together. 

ADAM MASTROIANNI: Yeah. Um, yeah. And which I think is helpful for seeing that like, not all questions are equally good affordances. Mm-Hmm.

Um, and this is, I think, a way that a lot of givers think is that if my statement has a question mark at the end, I'm doing something prosocial. But like some questions are bad. They're dead ends. Like how many cousins do you have? Uh, it's like the answer is a number and it doesn't open up anything else.

Um, but other questions, open things, uh, up, like usually starting with like, how do you feel? Or like, what was that like thing, like things that, that allow for open-ended answers rather than multiple choice, uh, or fill in the blank. Yes. Um, and, uh, and similarly taking can create affordances too that the people who are often fun to talk to, who are a little bit ridiculous in conversations, they give you something to react to.

Even if they didn't ask you to join in, they're playing a game, you know, it's like someone's like kicking a ball [00:25:00] around and you can go kick it with them. They don't have to say, Hey, do you wanna kick this ball? They're making a fun thing. You can join it. Now, now that said, I'm sure all those people who make you feel drained, like they should learn how to ask a question too.

Uh, it's not just that like everyone's actually doing the right thing all the time, but I think something that could open up people's ability to talk to one another is recognizing what, which strategy someone is playing and trying to play it with them and appreciate the strategy that, that they're playing.

And I find I do this now sometimes with people who sometimes frustrate me, that they never ask me a question. I'm like, okay, I'm not, I'm gonna stop asking questions too. I'm gonna play the same strategy. I'm gonna take two. Um, yes. And uh, and the thing, this thing crashes and burns one of us has to give. Uh, but, but otherwise, like, maybe we can have fun playing the game that the way the other person usually plays it.

ILANA GILOVICH: I love this because I think it's quite empowering then you're making particularly givers, but anyone not feel a victim of a bad conversation. You actually have quite a bit of agency in how you determine the course of that conversation. Do [00:26:00] you, do you prefer having conversations with givers or takers if you were forced to choose?

ADAM MASTROIANNI: Uh, man, it really depends on what I'm trying to, to do that like, uh. I have friends who are really, I mean, doing improv. Some, some friends who are really funny and entertaining and I'm totally happy, uh, for them to like put on the show and I'll do some cameos in the show. Um, yeah. But, uh, but I like the show.

I'm happy to watch the show. Um, and I have other friends who are really good at giving and we won't necessarily do the same thing, um, where like, it's not, it's not razzle dazzle in the same way, but I can like talk about my inner states in a way that I couldn't with someone who's only good at taking. I feel a concern for people who are like stuck in one mode or the other.

Yes. That there are like parts of themselves that they never really get to explore with other people because it's always showtime, uh, or it's, it's always therapy. Um, wow. Neither, neither of those things are, uh, like both of those things can be good on their own, but you don't wanna spend all of your time on one or the other.

ILANA GILOVICH: [00:27:00] Right when it's relentless. Actually, speaking of those two kind of valences for a conversation, um, kind of a chicken or the egg question, what came first? The psychology or the, the comedy, because I can see how they're both a way to sort of meditatively stand back and understand human nature and do you feel like one was your earlier passion that further the other one, or they sort of grew up in tandem?

ADAM MASTROIANNI: Uh, it was, it was comedy first as, uh, as a kid I watched a lot of standup on TV and I would do standup at, um, at, uh, like, um, talent shows, which I went to a Catholic school for el for elementary school. So, uh, they were, they were pretty tame. Um, lot of censored material. Yes. Um, yeah. When Priest is in the audience, um, you, you do a different kind of set.

ILANA GILOVICH: But I bet you got great fodder for your later standup career. 

ADAM MASTROIANNI: Uh, yeah. You know, I, uh, I later, uh, when I went to the, the Fringe Festival for a couple years, uh, I, I performed a show called Standup [00:28:00] History, where I did a set on the Apostle Paul that always went down a peach, as they say, over, over there. It was fine.

Uh. But, uh, but yeah, it was, it was comedy first. In college, I tried to put them together. My senior thesis was on the psychology of Humor, and what I learned was I wanna do these things separately and not together because it really, it didn't feel like they were more than the sum of their parts. And it also didn't feel like I.

I was actually gaining insight into what I loved about comedy by doing psychology on it. And it didn't feel like I was doing very good psychology by doing it on comedy. Um, that it sort of felt like trying to figure out like what makes something beautiful that, like, the question sounds interesting, but it's actually miss specified because like, we mean beautiful means a lot of different things.

And like what you say about one piece of it is, is either gonna be. Too specific to be useful or too broad to be useful. Like it's gonna be either pointless or trite. And, um, and that's where I feel like I, I got with it. So I, uh, I, I separated them, uh, for both of their benefit in my life [00:29:00] afterward. 

ILANA GILOVICH: That's wonderful.

I think, I think with academic inquiry. I've found that if it's an object that I really love, like a film or a book, and I bring sustained scrutiny to it, that actually works really well because I don't end up hating it, but I just get more and more exposed to it. So I can kind of play the melody in a deeper way with my analysis.

But if it's a big question and I'm forced to stick to it academically, I think that's when I can get sick of the question for exactly the reasons you describe. 

ADAM MASTROIANNI: Yeah, that's really interesting. 'cause I think some things have that property of the more you look, the more they give. 

Comedy feels like one of those things where uh, actually your best experience is a shallow one.

Um, where the point, like the joke doesn't get funnier. The more you study it, it immediately gets less funny. Um, and, uh, this is why I if, if I could choose between going to see a comedy show and a magic show, I'll always see a magic show because [00:30:00] I know so much less about it. So I can, I can, uh, appreciate it that like the whole point of it is, um, there's supposed to be a mystery here.

Um, like this isn't an academic exercise. Like it would feel like going to a comedy show where it's like, okay, they had this structure and like they did this callback. Like, here's this setup. I'm like. You can, that might be intellectually fulfilling, but it's not entertainment anymore. Um, yes. Imagine something like a film, I mean, or like a drama that like it's meant to be felt and you actually might be able to feel it more, setting it more.

ILANA GILOVICH: I would love to ask you a little bit about language, which feels tangential to the comedy question because your incredible substack experimental history, you use language in such a disarming, destabilizing way. So I'm gonna read some of the titles of your sub pieces. How many people has Dolly Parton killed?

You should not open a door and see someone pooping help. There's a dead CEO in my head. Excuse me, but [00:31:00] why are you eating so many frogs? This movie has 3% on Rotten Tomatoes, and I'm in it. So can you talk to me about your use of words in conversation, both to comedic effect and to really carry a point and to draw a reader in, in a very surprising way?

ADAM MASTROIANNI: Yeah. Uh, I guess it doesn't feel all that deliberate because I am mainly, uh, being myself that, um, it kind of feels like, uh. Uh, especially when you write on the internet, um, or when you write anything, it it, there's a temptation to adopt someone else's voice to do an impersonation of like a writer who that is better than yourself.

Um, this is one reason why I. Don't like writing journal articles very much. Yes. I feel like I lose 50 IQ points trying to write them, and I don't have that many despair in the first place because I'm trying to write in a voice that's not mine. It's like speaking a third language. Yes. Like my vocabulary is more limited and so I can't express myself.

Um, but when I'm writing for myself on experimental history, I can see exactly what I mean. [00:32:00] I think that when you say exactly what you mean, it is often funny without trying that, uh, that often when people find funny, it's just like people being themselves. Um, you know, most of the time when people laugh, it is because they're around other people that they like being themselves, right?

That the, the thing that makes people laugh most often is not a deliberate joke. It is, yes. The circumstances of their lives. Um, and so that's what I'm trying to do there is let myself be exactly that. Um. And I can feel the times I'm actually grinding against it. Like one title you didn't read is, uh, you'll forget most of what you learned.

What, what should you do about that? Which is a title that IWI would like go back. I would not give that title again because it felt like I'm trying to do an impression of like the title of an Atlantic, uh, yes. Article. Oh my God. Totally. Uh, and like I can't outdo those things. Like I can't outdo the people who do that.

Well. Um, what I can do better than anyone else is write the way that I write. Um, and when I write, I ask you, how many people has Dolly Parton killed? [00:33:00] Uh, 

ILANA GILOVICH: which we infinitely prefer. 

ADAM MASTROIANNI: Yeah. Yeah. 

ILANA GILOVICH: A pitfall of conversation is people want to show up as their authentic selves. They think the conversation would be further by doing that, but they just feel too apprehensive.

So, 

what do you do to get into that place that sort of mutes all the other voices and really hones in on Adam's voice? 

ADAM MASTROIANNI: Yeah, in the moment it's difficult 'cause once you're in, in it, uh, like all you can really do is pay attention to it. But there are a few. Thoughts that have occurred to me that have made this easier.

One of 'em comes from writing online and, uh, and realizing when, whenever something gets enough people seeing it, inevitably someone is going to love it and someone is going to hate it. Like these facts are, are, are trivial about the world. In a world of 8 billion people, uh, the fact that someone feels a certain way about a thing is not news.

It's an inevitability. Mm-Hmm. Like all possible answers will be given. So the fact that someone like likes what you have to give them or doesn't like it, uh, like. It doesn't really matter. It feels diagnostic. It isn't. And then you can get into [00:34:00] like, well, but on average, do people like it or, or not? But like now you're, when you wanna take the average of the, of 8 billion people or the average of everyone who ever encounters this thing.

And it's not that you shouldn't care about what other people feel, but you should tune in as much as you can to how you feel about this, which I think is pretty naturally going to reflect the responses that other people give you. Uh, but like I can feel myself liking someone, something less. When I feel that it doesn't, it's not connecting with people in the way that I think that it should.

Like if I'm explaining an idea and, uh, and they're like not getting it 

I want to make the idea better or drop it, uh, or express it in a better way. Like, I don't wanna double down. Um, yes. I think most people are actually like that. Like you can probably think of a few people who barrel ahead when they shouldn't.

Yeah. And most people, I think like the, these, these levers are connected in their head. Um. So that makes it easier for me when like, I'm being myself in a conversation and someone doesn't like it that much. I'm like, Hey, it's not for everybody. 

ILANA GILOVICH: Yeah. It's an acquired taste. Yeah. 

ADAM MASTROIANNI: Yeah. Just like, I wanna make sure they feel okay, but like, if they don't like my [00:35:00] stories of my personality or, or whatever, uh, just like if I was doing an improv show and someone didn't like it, I'd be like, well, but there's other people in this room.

Like, I'm playing, I'm playing the, the kind of thing that I like to play. It's for the people who like to watch that. It's not to please every single person. Because that thing that pleases everybody, excites no one. It, it's like hotel room art, like room art. It uh, it's not meant to be looked at or appreciated it.

It's meant to like be banal. 

ILANA GILOVICH: Yes. I love that. And I also think. As somebody who has struggled with people pleasing or trying to accommodate the other person, I find that when I'm able to transcend or shed that and really show up as my authentic self, the people that I genuinely want will gravitate towards me.

And so then you end up not feeling exhausted by conversations. You end up getting art sent to you that you love because you've put your art out into the world. And there's a kinship and twin ship there. And that's 

a fantastic, uh, feedback rich cycle. 

ADAM MASTROIANNI: Yeah, yeah, people, [00:36:00] uh, you, you attract the right kind of person.

Um. I find this too writing online, but like, yes, I would like my number to go up. Uh, but I want it to go up because I'm reaching the right kind of people. Yes. And so, uh, if you like obsessive your substack metrics too much, you can see that like sometimes people unsubscribe and uh, each time I'm like.

Actually I am, uh, that person wasn't liking what I was doing. It's better for them to not be here. Uh, like the last thing I wanna do is put an email in someone's inbox that they don't wish to have. Yes. Like, I wanna be in the inboxes that want me there. 

And so this is like honing uh uh Yeah. Honing your craft.

Like, it, it, it's trying to get it to the people who appreciate it. 

ILANA GILOVICH: I would love to switch gears for a second and ask you about another study that's related to conversation that you have, which is about the many minds problem and thinking about group dynamics versus diadic conversation. So would you be willing to talk a little bit about that?

ADAM MASTROIANNI: Yeah, yeah. Uh, so in psychology we, we, you know, study conversation, but, [00:37:00] uh, but like. Like every abstraction, it puts a lot of things together that aren't really like one another. And talking to one other person seems like it might be like talking to multiple people, but in fact, changes in some fundamental ways that when we are talking, uh, the, the element of one of the fundamental elements of conversation called turn taking, which is just who goes next, right?

Pretty simple. If I'm not going, you're going or we're silent. Like that's it. Yeah. Uh, when there's three people now at the end of each person's turn, it could be either there. There are turns to go. As you add more people, it becomes more and more complicated as to who should go next. And, uh, and so we didn't do this research, but some research finds that like all of these things spring up in larger group conversations to try to navigate this massive turn-taking, like people will bid for the floor.

Uh, you know, they'll do little vocalizations that, that, uh, ah, when someone like speaks up a little bit like, oh, uh, like that, that's them trying to take their turn. Or people will nominate the next speaker. By looking at them. Um, uh, and these are things that don't really need to happen in a two person [00:38:00] conversation, um, or happen on a much smaller scale.

Right? But like, if I'm going on for too long, you might start to like, nod a lot or lean in closer or like move in such, such a way that signal that like you would like to take a turn. But it's a lot less complicated. Same thing with trying to tailor your statements for a larger audience that, like, when it's just two of us, I mean, it's hard enough to know how you might react to each thing or keep track of like, what are the things that I will share with you won't share with you at another person.

Now it's like I have to do like another person's taxes basically, and then another person, like I have to account for them. Uh, and it gets a lot harder to, to basically be yourself when you have to tailor your content for people whose preferences are non overlapping. Mm. Um, so those are a few of the things that, that pop up when, um, uh, when, when we talk in larger groups of people.

Um, which I think is also why larger groups tend to be unstable. Um, yeah. There's one paper that basically claims that like any group over five is unstable and you can watch it collapse. I don't think that's, that's like a. [00:39:00] A universal rule, but if you watch, uh, in a group that's larger than five, if, if the affordances allow them to collapse, I mean it often will because it's not that fun to never be able to take a turn and to have to, yeah, to cater your statements for this larger group.

Much more fun to turn to the person next to you and start a little side conversation. You pull someone in and now you're just talking to three people. Um. So, I dunno, uh, look out when you're in the next group to see like, how big does the group get before people start talking to the person next to them?

ILANA GILOVICH: Wow. It's, yeah, it's funny. It's, it's high risk, high reward because I've been in conversations with a group of 15 people that was fantastic and hysterical and quite giddy. But that was usually launched by a very specific prompt that everyone enrolled in. 

ADAM MASTROIANNI: Yeah. And so, uh, often what can make that those larger conversations work is like we've all agreed to the turn taking pattern, which might be that we're doing an exercise where each of us goes, you know, the person to, to your left tells their life story and then the [00:40:00] person to their left Yeah.

Or someone's in charge. Um, right. We have a traffic cop basically deciding who's gonna go next. Uh, that's why you have a facilitator for a large group that you don't have for two people. Um, 

ILANA GILOVICH: right. 

ADAM MASTROIANNI: Uh, you don't need them. 

ILANA GILOVICH: Wow is, do you have a wish for, for either group conversations or one-on-one conversations that if you could see out in the world, if listeners could take away one thing about how to have more stimulating, nourishing conversations?

ADAM MASTROIANNI: Uh, yeah, I think it's the, the second rule of improv. So everyone's familiar with the idea of yes and right. That, that, uh, I agree to the reality that you propose and I, and I add to it. Um, that's great. Uh, I think that's a good rule. I think it's often been oversold that we're, you know, we're trying to sell corporate trainings to Microsoft with Yes.

And that's fine. We gotta make money somehow. So yes and is good. Um, but there's a, a rule of improv that like even better, which is treat your senior partner like a genius, um, which is basically like act as if it is possible for your partner to say [00:41:00] something smart and interesting. And you may find that they will.

Uh, and this works really well in an improv scene. When someone does something that you might think is stupid, that if you treat it like a good decision, you can make it one. Um, wow. That, uh, that if someone starts a scene in a sewer, rather than be like, oh God, we're in a sewer. Be like, maybe they had a fun idea for why we're in a sewer.

And maybe that means I can also have a fun scene in a sewer. Actually, I'd love to do it in improv scene in a, in a sewer. I don't think, I dunno if I've ever done one. Uh, it's too hard to mime climbing down the, the manhole. Um, but in a conversation, um, I often find that like, when people don't treat me this way, I am a less interesting version of myself.

Um hmm. And often it comes from like offering someone an affordance that they don't take, um, that, uh, that I'll be like, oh yeah, uh. I don't even know what they'll, they'll ask like, oh, you were on a, a reality show in the, the uk. Be like, yeah, it was pretty crazy. And I'll go like, yeah, sounds crazy. Anyway.

Like they'll be like, no, there was, there's a story [00:42:00] there. You gotta like open that door. There's something behind it. I promise you'll have a good time. Spin it into gold. When I see people do this with one another, I'm like, open the doors when you're giving each other gifts, unwrap them, act as if the other person is, it's possible for them to give you something that, that you might find interesting.

ILANA GILOVICH: I think that is the best advice about conversation I've ever heard. I. And I've been recording a lot of these episodes and it's a really like gal beautiful galvanizing and really benevolent way to think about conversation because I think we're very want to get frustrated and annoyed and eye rolly. And so the idea that we could really live into the idealized version of our conversational partners, really sweet.

ADAM MASTROIANNI: Yeah. Yeah. Some, some people, uh, also have to be convinced that they can be a genius in this way. That, that, um, I, I've, I'm always interested in like, what do people actually do at their jobs? Um, because I haven't had a lot of like, the conventional jobs, like, but what is it that you are doing from nine to five every day?

Like, and people [00:43:00] think this is very boring because they do it, but I'm like, no, it's weird to me that you like, make PowerPoint presentations. What's in them? How do you make it? What, like what is this? Like, this is weird. And I think when you treat it that way, people will be like, yeah, it is actually weird that I make PowerPoint presentations about like the density of calcium in people's bones to like try to sell medicines to pharmaceutical or whatever it is.

Yeah, there's something there. It may not be able to sustain us for like two hours, but for 10 minutes. Like we can talk about the thing that you spend 40 hours on every week. 

ILANA GILOVICH: Hmm. Yeah. You used the word bloom a little while back, and I love that idea of like, what allow your conversational partner to bloom with under the sunlight of your attention.

That's so beautiful. Yeah. Yeah. Well, you brought up the cooking show and that was going to be my concluding question, and I feel that I'm at a point where I'm like, I think the conversation could end, not because I haven't been delighted by having a conversation with you, but I'm cognizant of time. It's getting close to the hour, and I feel like.[00:44:00] 

How are we gonna end on a better note than the gem of the advice that you just gave me? How are you feeling? Would you have wanted the conversation to end earlier, later? Does this feel somewhat close to the mark? 

ADAM MASTROIANNI: I feel great about this because you signaled it, right? Uh, the idea that, that we're going to end, we're not ending now.

Um hmm. Uh, I think is a nice way to do it because when you spring it on someone, it's like, well, is this something I just said that maybe you want to go, uh, but this really sounds like it was planned. Like, I can't see your screen, but maybe you had 10 questions and we just asked number nine. And naturally, here's number 10.

There could have been 50 more, and you're like, oh man, they could cross those out. Like, we, uh, this isn't going so well. I don't know, and I don't have to know. Uh, I'm just having a, a nice time. So, uh, so yeah, let's, let's do one more and go. 

ILANA GILOVICH: How do we prepare to meet an end artfully, whether it's a conversational ending or that grand ending of death?

None of us know or can predict how an ending might occur. In the case of any ending, all we can do is greet it with grit, grace, humor, and [00:45:00] goodwill. Now we embrace another ending with the conclusion of liftoff in the artist's way. Author Julia Cameron writes, art lies in the moment of encounter. We meet our truth and we meet ourselves.

We meet ourselves and we meet our self expression. We become original because we become something specific and origin from which work flows. When we bring all of ourselves to conversation, our sincerity, our lived experience, our dreams and fears, our most audacious forms of imagination, conversation can become a safe harbor, a giddy playground, a laboratory for ideas.

When listening back to these episodes, I realized that I was often working through an idea with different conversational partners. Having enriching conversations with multiple people allowed me to tease out key themes from my own internal landscape. Conversation allows us to unearth what is important to us and others,

dearest [00:46:00] listeners, I hope you leave liftoff with an increased awareness of conversations, dormant, artistic potential. We can talk or we can really talk. The poet, Gregory Orr writes if we're not supposed to dance. Why all this music? It is my hope that liftoff has helped you hear conversations inherent music.

Now it's time to truly converse. Go Dance.

Liftoff was created and directed by Ilana Gilovich and produced by Greg Hanson. The featured guests on this episode were Alison Wood Brooks Max Stossel, Tess of Velasquez, Tom Gilovich, Mallory Gracenin and Adam Mastroianni. Special thanks to all of our podcast guests on the series, as well as our incredible graphic designer, Alex Kaufman.

A heartfelt thanks to everyone who donated to this podcast GoFundMe campaign to make this project possible. Thank you to the friends who provided feedback [00:47:00] on this project. Max Stossel, Becca Kaufman, Christina Aldrich, Anneke Jong, Andi Nash, and especially the brilliant Athena Diaconis. If you like liftoff, please share it with your friends and be sure to subscribe wherever you listen to podcasts, so the power of potent and playful conversation can continue.