Episode Transcript
[00:00:00] Speaker A: In entrepreneurship, I mean, one of the central tenets is done is always better than perfect and you can iterate over time. And I think journalism is very similar. And that attitude of needing to overcome perfectionism and understanding that you do your best is very important in kind of getting over the self imposed hurdles that so many people erect for themselves.
[00:00:23] Speaker B: Well, thank you so much, Dory, for being here.
I don't think you need an introduction. Most people know who you are. But for those who don't know who Dori Clark is, we actually kind of go back to Pre Covid. Just before COVID We met just before all hell broke loose.
[00:00:39] Speaker A: It's true, it's true.
[00:00:41] Speaker B: And we both started our careers in weekly journalism and we worked together for a while and you got me motivated to get it deeper into this entrepreneurial game. So thank you.
[00:00:52] Speaker A: I know, and I'm so happy you started this, this podcast. I was so excited to accept your invitation.
[00:00:59] Speaker B: You kind of suggested it Dory, way back when.
[00:01:02] Speaker A: Well, what a. What a good idea.
[00:01:04] Speaker B: Yeah. Thank you. And I've read all of Dory's books, including her latest, the Long Game. Actually, I should be talking to you because you're right here and it's really good. And I also really identified with the long loneliness that you talk about in the beginning of the book about, you know, when you're working the long game. It's kind of a lonely thing. And Dory has become the number one communication coach in the world. She's been named one of the top 50 business thinkers three times.
[00:01:32] Speaker A: Born out as of last week.
[00:01:35] Speaker B: Congratulations. Oh, my God.
[00:01:38] Speaker A: Yeah, thank you.
[00:01:39] Speaker B: She's also someone who knows about loss, about the long road, and about learning to say no. And I'm just so psyched that you didn't say no to me.
[00:01:48] Speaker A: Never. Never. Thanks, Diana. I'm so glad to be on.
[00:01:51] Speaker B: So I thought it would be fun to start this podcast recording with. What's your morning routine?
[00:01:58] Speaker A: I'm not one of the people that has a very regimented morning routine. I. I think I totally respect people who do. But, you know, I'm traveling a lot. I. I have like a few different places that I live, and so things are a little bit different in each place, which creates a different set of circumstances. So there's things I always try to do in Miami, for instance, where it is much more feasible and I have a great outdoor space and it is actually pleasant most of the year.
I try to go outside in the morning and drink coffee outside so I can get, you know, the amazing sunlight in your eyeballs to reset your circadian rhythms. That is less possible in New York because, you know, I. I don't have, like, an outdoor terr or whatever, and so I don't always get a chance to go outside first thing. But in general, I try to make sure that I am making coffee for myself and I make a nice latte for my wife. We got married about a year ago. And one of the ways that I have tried to show her love and affection is, number one, convincing her to stop drinking diet soda, which I feel is harmful.
It's getting her addicted to really, really good coffee. So my part of the bargain is that I make it for her. Every.
[00:03:16] Speaker B: That's fantastic. And I actually do the same. Try to remind myself, no diet soda. Coffee instead. Yeah.
[00:03:23] Speaker A: Yes. Love it.
[00:03:24] Speaker B: Congratulations on your marriage.
[00:03:26] Speaker A: Thank you so much. Yeah.
[00:03:28] Speaker B: So I guess the loneliness is a little better now.
[00:03:31] Speaker A: Yeah, it's. It's always. It's always much nicer when you have somebody. Somebody fun to share things with. And, you know, we.
We still have some geographic struggles because she has a job that requires her to be, you know, in one place at least several days a week, and I'm often in a different place. But we. We work it out and we end up spending a lot of time together, which is great.
[00:03:56] Speaker B: How did you keep going during those hard years?
[00:03:58] Speaker A: Those hard years of. Of not having a beautiful wife?
[00:04:00] Speaker B: Yes.
[00:04:03] Speaker A: Yeah.
[00:04:03] Speaker B: Well, first of all, I'm also. I get car sick in these cab rides to the airport, too. So I thought of you all day yesterday. Cause I. I'm here in West Palm beach at the Eudaimonia Conference on wellness.
[00:04:13] Speaker A: Oh, nice.
[00:04:14] Speaker B: Andrew Huberman, who, you know, you kind of quoted, you know, but the eyeballs and the light.
[00:04:19] Speaker A: Yes, yes.
[00:04:20] Speaker B: It's going to be here. So I thought of you on my way to the airport yesterday. I was like, I feel so sick. This is how Dory feels all the time.
[00:04:26] Speaker A: Oh, I know. That's so terrible. I'm so sorry. Have you discovered the funny French sailor goggles? Do you know what I'm talking about? No.
Okay. There is a product. There's like, knockoffs you can get on Amazon, which I don't know if they're effective or not, but I. I paid, you know, the. I paid the. The extra fee to get the original thing. But I was so fascinated when this first came out probably about eight years ago. There's a product called Boarding Ring, and the origin story of it is that it was developed by the French navy for sea seq sailors. And it's these absolutely ludicrous looking, you know, Mr. Magoo kind of glasses that have a blue liquid in them. And the liquid sort of rocks around so that apparently it's a way of orienting your sight line to the horizon so you become less motion sick. And they have it on the front and on the sides. So it's like you're wearing glasses that have four little glasses, holes and you look completely weird. But, but I nonetheless, you know, utility first. I wear them in the cab. And it actually really helps. Like I would say it doesn't cure it a hundred percent. Like, I've still gotten kind of ill sometimes, but I would say it probably cures at 85 to 90%, which is a wonderful rate of improvement. So that is, that is my suggestion for you.
[00:05:50] Speaker B: Thank you. Because those cab rides would be perfect to get work done in, you know.
[00:05:54] Speaker A: And it's just like, that's the worst.
[00:05:55] Speaker B: Thing you can do though, is look at your phone.
[00:05:57] Speaker A: Oh my God. Yeah, I don't even try to get work done. Mostly I just concentrate on like not vomiting or not getting so sick that I'm messed up for the rest of the day. So if I can do that, it's a win. But boarding ring really does help with that. But to answer your question, it's kind of an interesting question when it comes to like dating or something like that. And I think it is a parallel for a lot of life because you kind of vacillate sometimes between trying to say, okay is the right answer to be extremely proactive and like, make your own luck and like go out and look and like, you're never going to find someone unless you're looking and, you know, whatever.
That's one, that's one train of thought. The other is, you know what, you can't force it. It just comes. It's going to come if it's going to come. And so maybe you should just be passively receptive and maybe you should just wait and you don't need to constantly be putting yourself out there. And I think like a lot of people, I sort of flipped between the two periodically, depending how disgusted I got with the, with the market.
But I just dispositionally, I'm always a little bit more on the proactive side because I like to have the feeling that I'm doing something.
So, you know, my wife was single for a long time before we met and she definitely was kind of extreme on one end and I was extreme on the other. I mean, I, you know, had a million dates and you Know, you have to sort of second guess yourself sometimes because it's like, well, why isn't it working? And is my conception of what I'm looking for not right? Like, you know, is it like, is, is there, is there a flaw in the theory? Like, should I be looking for the opposite of what I think I'm looking for? Maybe that's the problem.
Anyway, I'm sure it's different for everyone. But what I can officially report back is that I knew all along what I was looking for. I just couldn't find it. And so when I did meet my wife, I was like, oh, this is like exactly what I've been looking for all along. I wish she had turned up 20 years before. But you know, it took, it took a while. Uh, but, but I, I, I did feel slightly affirmed that my self knowledge was, was decent.
[00:07:58] Speaker B: Yeah. There's a quote in your long game book. We have to be willing to do hard, laborious, ungratifying things today. The kinds of things that make little sense in the short term so we can enjoy exponential results in the future. Now I'm not gonna, I just love that because it's, it's, it's like if you were to put that on a, on, on like a sales on a placard, on a, on a billboard. I don't think people really, really want to hear that.
[00:08:21] Speaker A: They totally don't want to hear it. No, it's so true. Do you have somebody special in your life right now? Like how do you, how do you come down on, on these issues?
[00:08:29] Speaker B: No, I feel like I'm like where you were back in the day when you're, Although I have to say I don't feel lonely.
I'm just so busy. Maybe I keep myself so busy that I just don't feel it.
And plus I'm, I'm in a lot of communities.
You know, I'm in 12 step communities. Whenever I do get that pang of loneliness, I just go to a meeting and then I'm fine.
[00:08:48] Speaker A: Yeah, you never want to sort of let it get to an acute level, I guess. And so it sounds like you have very good mechanisms for, for thinking through that. But yeah, I hope I, I hope you meet somebody awesome because that would be a nice plus, you know.
[00:09:02] Speaker B: Oh, thank you. Yeah. And Esmond, you know, our, our mutual friend Esmond was a really, really dear friend, even though he was never like a romantic person for me, but you know, probably my best friend in the world.
[00:09:12] Speaker A: Yeah. Oh my gosh. And I am so sorry for, for your Loss with that. I mean, you know, I. I knew him much, much less well, but he was still a really special person. But it's. It's terrible because I know he was just a lifelong friend for you.
[00:09:25] Speaker B: Yeah. He was so excited to start working with you. I remember I had lunch, dinner with him in New York in January, I think it was. He's like, I've got something to tell you.
[00:09:33] Speaker A: I'm like, what? I'm working with Dory. I'm like, oh, my God.
Oh, I know. It's really. It's really awful.
Yeah.
[00:09:42] Speaker B: So the loneliness topic makes me segue into your theological studies at Harvard Divinity School. That has always intrigued me because I've always felt that you have this. This aura about you. And I don't know if it's dory just your nature or if it's something that you also got from this master's degree that you got there.
[00:10:03] Speaker A: My saintly aura, you mean?
A lot of what you are is.
[00:10:07] Speaker B: About service and helping other people, and. And I don't know if that's.
That's the way you show up. And I'm just wondering whether that's something you already had, that you then deepened with this. This study that you did at Harvard. In my view, you know, wellness encompasses spirituality. Can you talk about that theological study that you did at Harvard and what it did for you?
[00:10:29] Speaker A: Yeah, absolutely. I definitely recommend the. You know, the. The study I did, I did a master's of theological studies, which was great.
I wouldn't say personally that I. I attribute sort of a service mentality to it, per se, in the sense that it really. At least for me, the way that I did it was an academic degree. It was like an academic degree in the study of religion, which was deeply interesting. I mean, it took all kinds of cool classes, from biblical exegesis to world religions. You know, I took a Introduction to Hinduism class. I took an Introduction to Celtic Paganism class. You know, all these awesome things that were. That were very interesting, but it wasn't so much about, you know, cultivating community or service per se. I think people come into the program with that, or maybe around the edges there's something like that, but it wasn't necessarily the focus.
But for me, when I think about the work that I do. And it's very kind of you to, you know, see a sort of service or community inflection.
I would say that it probably comes from something different, something really intriguing that I heard once from a colleague of mine. There's a guy that I know named David Holman, who wrote a book, I think this year or last year, which was a study of like networking and, you know, connections and things like that. And one of their findings, it was him and a guy who's a colleague of his, who's an academic, they did a study and one of their conclusions that David told me about was that of the people that they spoke to who were, you know, either self identified or identified by others as being connectors in almost all the cases when they talked to the people, the connecting that they did was essentially like a kind of trauma response. I feel like, I feel like you're gonna dig this because it's, it's like, you know, I think essentially a way of trying to counteract maybe experiences that you've had of feeling left out or excluded or whatever, and then you want to try to create a space for other people.
And I won't say that I had that in any acute kind of way. I mean, it was not like, you know, some kind of outcast or something like that. I was always decently popular in school and things like that. But, but I am definitely attuned to, to the idea of, like, it just, it upsets me when there are circumstances that are set up and, and sometimes they're set up purposefully and sometimes they're just set up like unintentionally, but in a careless way that make some people feel bad and, you know, because they're, they're creating or exacerbating some kind of status thing where some people feel in and some people feel out. And it just, it honestly just offends me at a very deep level. And I don't, I don't think it's cool. Like, it's not cool to put other people down. And it's not cool to be so thoughtless as to do that and not recognize it. And so I like creating a space where, you know, everybody feels good and everybody feels like they belong there and they should belong there.
[00:13:44] Speaker B: Yeah. And like our. You have that wonderful friend with the croissant.
[00:13:49] Speaker A: Yes. Robbie Samuels, come up with the idea of, of the networking idea of bagels and croissants, which is, which is really lovely. The, the, the quick primer for anybody who is not familiar with that. Robbie's given it like a TedX. Talk about it is that when you are at an event, most people stand in a closed circle, like a bagel. And, but that is not the move if you want to be inclusive. You should stand in an open circle like a croissant. So that people feel okay approaching you and coming in to join your group.
[00:14:19] Speaker B: I love that. And I remember the first time I went to Renaissance Weekend, you made sure that I had friends down there. I just thought that was very sweet and very kind of you.
[00:14:28] Speaker A: Thank you, Diana. That's really nice.
[00:14:30] Speaker B: It's maybe just natural for you to be that way, then.
[00:14:32] Speaker A: Well, I don't know if it's. If it's natural necessarily, but, you know, I think that, like, you know, like, a lot of things, you know, we all. We all have our kind of lens of where we come from, and I think that probably a lot of things were impacted. I mean, you know, it's like. It's like, you know, these early years are pretty formative, but, you know, I grew up, you know, gay, in this small town in the south. And so even if I wasn't in an active way, being, like, excluded or anything like that, it gives you a little bit of a different lens where you're. You're sort of looking at things like, okay, this is not.
It's. It's like you're not like the fish in water. Exactly. You know, like, if you're a fish in water, it's like, oh, this is just how things are. This is the normal way that everything is. You know, why would anything be different? And you don't. You don't think about it at all. But if you have. For. For whatever reason, whether it's, you know, a race or gender or sexual orientation or money or whatever it is, if you have a slightly different lens and you're sort of the fish that's outside the water, it's like, okay, well, let's. Let's interrogate this a little bit more. And I think I probably had something along those lines. How do you feel like your lens around community and inclusion was shaped? Like, how do you think about those things?
[00:15:52] Speaker B: Well, like you. I was never unpopular, but I didn't feel like I was swimming like a fish like everybody else because of my.
I've since learned there's a name for it. It's called adult third culture kid.
I moved so many times. You know, I grew up. I was born in Chicago, raised, like. Started off in Florida, in Ocala. My father wanted to be a cattle rancher, and then he missed the mountains. We went back to Switzerland, then from. My parents separated, I went to a castle in France and then to Monte Carlo and then to Newport, Rhode island, and then Boston, Massachusetts.
[00:16:28] Speaker A: I mean, that's a lot. Yeah.
[00:16:30] Speaker B: And then ger. I mean, I. I just. When People ask me where home is. I don't know where home is, you know, and it's so. I never really felt like I belonged. And I don't know, wherever I am, I'm always the sort of the external person, so I've had to adapt. Does that link up to that feeling that you had down the south when you were.
[00:16:49] Speaker A: Yeah, yeah, for sure. I mean, you know, I was in one place my whole childhood, so I mean, that was sort of a standard variable. But certainly, I mean, you can, you can have a men, you know, a mental orientation, even if it's. Even. Even if you're sort of static in a physical orientation. And it just seemed like, you know, everybody's like doing their thing, but that is not the thing I want to do.
[00:17:15] Speaker B: I have to say the, the 12 steps meetings have given me a sense of belonging. And what else has given me belonging? I think work, being a worker bee, being in an expat community. When I was living in Lausanne, you hang out with other expats who are also adult culture kids, and they also get it. So.
So it's finding those communities to plug into that that helps.
[00:17:38] Speaker A: Yeah, absolutely. You. You want to find a place where you can really. Where you can really fit in. And, and it's also interesting because it's. You, you know, it's always worth interrogating too, like in the places where one fits. Like how.
Because anything, you know, can. Can become sort of an insider, outsider thing. And I'm sure this is not the case for you at all, but like, you know, my dad growing up, my dad was like very big into 12 step things. He was an alcoholic and he like, got really, really into 12 steps the way that some people really, really can. And, you know, that was. That was great for him. That was amazing. Like, he really felt like he found his home. But it was interesting because it was kind of to the exclusion of his family. Like my mom and I, like, like, I think he was disappointed that we weren't alcoholics because it was just like it was such a thing for him. That was really where he preferred to be. And so he was kind of checked out in other aspects of his life. And so it's always just an interesting thing. It's like, it's so wonderful when people can find a home. And it's also like, oh, okay. We have to, you know, always sort of check ourselves a little bit to not dive in so much that it becomes, you know, that the excluded becomes the excluder in some ways.
[00:18:54] Speaker B: Oh, good point. I have to Remember not to do that with my family. Thank you.
[00:18:58] Speaker A: I'm sure you don't.
[00:19:01] Speaker B: Oh, that's so funny. Yeah. And there's another lens that, that makes it difficult when you grow up in a family that has money.
I remember when we first moved to the U.S. one of my neighbors had a Bentley and one time my mother's car didn't start and they gave us a ride to school in a Buntley. And I got so, oh, gosh, bullied that day from all the kids at school.
[00:19:23] Speaker A: Wow.
[00:19:24] Speaker B: Again, are we missing the bus?
[00:19:27] Speaker A: And what did the bullying look like? I grew up in a, you know, perfectly nice community. I'd say it was sort of an upper middle class community, but there were no Bentleys. But I can imagine if somebody went to school in a Bentley, it wouldn't be a bullying thing. I feel like the kids would be like, oh, holy shit, that's so cool. You know, can we ride in it? So like we're like, what did it look like? Was it just like a, like just a pure jealousy attack or what happened there?
[00:19:51] Speaker B: We were so different. We had just moved to the U.S. my English was not very good and my mother had me dressed in sort of little European dresses. And so we look different, we sounded different. Here we show up in some Bentley. We were just so different.
[00:20:05] Speaker A: So you're just like total outsider kind of thing. I got it.
[00:20:09] Speaker B: Mom, can we get some corduroys and some running shoes, please? Like I need to fit in. Yeah. And it was so hard. I think they just, a lot of people just ignored me maybe, and they felt uncomfortable and they would whisper to each other and, and I just felt.
[00:20:24] Speaker A: Yeah, that must have been so hard.
[00:20:26] Speaker B: Yeah, really, really hard. And then I then ended up getting sick. I had a head appendinitis that nearly killed me. And then the peritonitis kept coming back.
[00:20:32] Speaker A: Oh, odd.
[00:20:33] Speaker B: I kept, I want. I was walking around like a monkey, you know, so the front bent over anyway, so people thought I was a very odd duck.
[00:20:40] Speaker A: Yeah. Oh, man, that is, that is really tough.
[00:20:44] Speaker B: Yeah. But I think feeling like you belong does help. I'm just curious, going back to the theological studies, how did they help you with your long, the long game, you know, patience, purpose, timing.
[00:20:55] Speaker A: In studying religion, of course. I mean, I guess the, the premise of, of much religion, certainly Christianity is like, you know, don't, don't worry. God will figure it out in the end. You know, like it doesn't, doesn't have to work out now. It doesn't have to make sense. Don't now, like, you know, it makes sense in the cosmic sense, not necessarily in the here and now.
And I know that's very comforting for some people. I'm not personally particularly religious. Like, I, I am, I am open to religion. Like, I love studying it. I think it's interesting. I would mostly consider myself an agnostic in the sense that it's like, you know, I, I mean, in all honesty, I feel like none of us really know, right? Like, we can think, we know, we can feel pretty confident, but if we, unless we want to be like fundamentalists, I think it's, it's pretty presumptuous to say, like, no, no, I know you don't know, but I know. And so I, I like to just take it all with a grain of salt and be like, you know what? It could, it could be right. Absolutely. Christianity could be right. Quote, unquote. Quote, unquote. Islam could be, Judaism, whatever. They could all be right. I don't know. And so I remain interested in them. I remain, you know, just like, compelled by learning about it because it's so powerful for so many people and it's, it's such an interesting way of informing beliefs about culture and society. I have to say though, that in terms of my own life, I'm a very justice oriented person. Like, it really bothers me on kind of a fundamental level when I feel like something is unfair or somebody, somebody's been taken advantage of or somebody's doing something like, like improper. And so I, I mean, this, and this is a central tension in Christianity, of course, is like, you know, of course people want to create a just world. And also there's the, like, be patient, God will decide.
I definitely err on the former side because again, being agnostic, I'm like, well, just in case, just in case they won't pay in the afterlife, let's make them pay now. That would be great. And so I am the person, to my wife's great chagrin, that if somebody like litters, I will go up to them and be like, why did you do that?
And, you know, I won't, I won't make them pick it up because that will usually entail like violence or something, but I will pick it up for them and I'll be like, I will just throw this away for you.
[00:23:11] Speaker B: And like, service oriented, Dory.
[00:23:17] Speaker A: I mean, service oriented and also like, don't freaking litter. Like, it's just wrong.
I really hate littering.
[00:23:25] Speaker B: Yeah, I was, I was thinking of your political campaigns that you've worked on. You Know, the kayaking and the river and, you know, remember that. That first lady.
[00:23:33] Speaker A: I. I do remember.
I'm impressed that you do. Yes, yes, I.
[00:23:39] Speaker B: For.
[00:23:39] Speaker A: For folks. For folks who are not so studied in my background.
Back in 2006, you were a baby back then. Yeah, I was consulting on a lieutenant governor's race in Massachusetts, and one of the, you know, the. The candidate that I worked for was a big kayaker. And so, you know, in politics, like, you use what you got. Right. And so she was big into kayaking, so we did a kayak tour around the state. And so she. I mean, like, all the rivers don't connect up perfectly, so it's not like she could go literally across the state in a kayak, but she would, you know, kayak in. In this river and then we'd drive her a little bit and she'd kayak in the next river. And so we. She'd hit, you know, as many towns as she could. And so. So yeah, we. We called it. We called it a whistle stop kayak tour, which didn't quite make sense, but it was. It was a metaphorical whistle.
[00:24:26] Speaker B: Yeah. And it was, you know, it was about who she was. But it also speaks to how you are so good at that book that you wrote, reinventing you. Right. It's all about reinvention. And, you know, you went to college at 14.
[00:24:39] Speaker A: I did. This little Southern town of which I spoke. I was very eager to get out of it, so I had a good incentive.
[00:24:45] Speaker B: Yuna, you worked at the Boston Phoenix, which is. Oh, true. Like, I love that. I think when I first heard that, I was like, oh, my God, she's a.
Because my first job was with an alternative news weekly as well.
[00:24:55] Speaker A: So it's such a storied part of our history, I think, you know, our, like, I mean, our collective national history, like alternative newsweeklies are, you know, basically defunct now. I mean, even the Village Voice, which was the most august of them, is like, I think now they might have a website or something, but I mean, it's been out of business. It's been resuscitated. Like, you know, there might literally be a handful of that are. That are left, but they're sort of in this emaciated state. But the idea of an alternative news weekly, it's. It's just. It's a powerful idea. You know, it was. It was a.
A countercultural newspaper that provided opinions as well as well researched reported stuff that was just, you know, truly presenting something alternative in a world where pre Internet, it was really Hard to get those insights and perspectives. So I felt like at that time, and I think certainly still in some quarters, but especially at that time, journalism was a very noble pursuit. It was really meaning to do something important in the culture. So I love it that we have that shared history, because the whole premise.
[00:26:09] Speaker B: Was the goal was to uncover injustice.
[00:26:12] Speaker A: Yeah, absolutely.
[00:26:14] Speaker B: Of journalism. And I think, you know, Bari Weiss at the Free Press does a lot of that still.
[00:26:21] Speaker A: And now Barry Weiss at CBS News, which is very interesting.
[00:26:25] Speaker B: So cool. Maybe people will start to emulate her and we'll have a little bit more. We'll have a return to honorable journalism, which I think would be great.
[00:26:33] Speaker A: Well, I mean, I'm incredibly impressed. You know, anytime there is, you know, especially a young woman who is able, in, you know, whatever, less than five years to create a startup from scratch that gets acquired for $150 million, I mean, it's. It's just deeply impressive how quickly she was able to mobilize something that was culturally relevant.
[00:26:56] Speaker B: And she was actually the only, like, newspaper making money. Like, I think it was like 2 million a year, I think, last time I was looking. But those deadlines. Dory, you've always said there's no such thing as writer's block, right? How did those weekly deadlines, the weekly rhythm, how has that shaped how you work now?
[00:27:12] Speaker A: I'm really so deeply impressed because you're, like, quoting me back to me. So you have really just done your homework. So thank you.
But, yeah, it's true. I mean, I think that one of the early, very powerful lessons that I had starting in weekly journalism is that so many people, I think, treat writing as this kind of, like, mystical thing where, you know, the muse has to descend on you and the circumstances have to be right. And, you know, quickly with journalism, you learn that it is, you know, it's. It's. It's very different. It's like, you know, writing like a fiction book or something versus writing for a newspaper. For a newspaper. And, you know, this, right? The paper will go out. The only question is, is the paper gonna. Gonna go out with your article in it or is there gonna be an enormous blank space and the editor is going to, like, write in the blank space? Dori Clark screwed up, you know, like. Like, you have to get it done. And so that pressure, I think, gets you comfortable.
You know, ideally, if you're. If you're doing well and you're keeping your job, it gets you comfortable with essentially satisficing, you know, that the article is never going to be Perfect. But, you know, is it, is it good enough? Is it, is it interesting enough? Is it, is there anything that is libelous in it? Okay, no. Good, let's go.
So I think that in entrepreneurship, I mean, one of the central tenets is done is always better than perfect and you can iterate over time. And I think journalism is very similar. They call it a first draft of history for a reason. It is a first draft and you may not get it right, but you try to get it right enough. And that attitude of needing to overcome perfectionism and understanding that, you know, you do your best is very important in kind of getting over the self imposed hurdles that so many people erect for themselves.
[00:29:08] Speaker B: Yeah, I like that. Self imposed hurdles, which could be ego.
[00:29:12] Speaker A: Absolutely. It could, it could be ego. It could, it could be the lack of ego. It could be, you know, a sort of failure of self esteem where they're so, they're, they're creating perfectionism as a barrier that, oh, it's not perfect. And, and so therefore, you know, no one ever has to judge your work because they don't see your work.
[00:29:30] Speaker B: Well, you were very valuable to me when you helped me edit a few pieces.
[00:29:35] Speaker A: Thank you.
[00:29:36] Speaker B: You're a very good editor, Dory.
[00:29:38] Speaker A: Oh, that's very kind. Well, you're a good writer, Diana. So back at ya.
[00:29:41] Speaker B: Ah, thank you. I wanted to get to the, the whole thing about saying no, that the long game talked about that. And actually when we were working together, I think you were encouraging me to say no to certain things because I tend to overbook myself. So what's the hardest no you've had to say recently?
[00:29:59] Speaker A: Oh, goodness.
I'll tell you one, I felt, I mean, I felt guilty, honestly.
It was. I said no to my, to my sweet wife. She had a talk that she was giving and it was like her first, like, big talk. It was at the University of Michigan. And they invited her in to speak to the, the big graduate school that they have there. And so it was, it was the large. I mean, I've seen her speak many times, but this was, I think, the largest audience and she wanted me there. And it was booked a long time ago and I said that I would come. And then my fall schedule materialized and fall is always the busiest season for me. I have a lot of my own speaking gigs and I, you know, like, right. Leading up to it, you know, I was in Dubai, I was in Dallas, I was in Los Angeles. The week after it, I had to go to London with her. And it was just so intense that I looked at it and that was the only thing that was essentially discretionary, you know. Cause the other things, it was like, it was work things. People were paying me money, you know, and I, I just said like, sweetie, look, it's, it's really too much. Like it will, it will kind of break me if I do this. And I'm really sorry, but I can't do it. And I know she was disappointed, but, but, and you know, I think the, the moral of this story is that some people would say, you know what the most important thing is Family. You should, you should be there for your family. Maybe it is. I don't know, maybe I may have made a mistake. But I also think that in this, in this calculus, I knew number one, you know, I, she knows I support her very much. And you know, I was like right there texting her before and texting her after. I had, you know, I've seen her speak before. But I also knew that she in the end would understand that I, I was just trying to carve out enough space so that I, so that I wouldn't get sick essentially, you know, that I, it, it had been so just ferocious with my schedule that this was a time, you know, if something is truly mandatory, I, of course want to do that and want to be there. But for the optional things, I think, you know, we have to be willing to make a call and to, and to just, you know, throw ourselves sometimes on people's mercy. But I knew it would be too much. And so I think part of it is just understanding what are your self imposed limits? I mean, I did feel bad about it, but I recognize that it would be extremely harmful for me to do it.
[00:32:26] Speaker B: But how do you know?
Is it a physical cue that tells you, ooh, this is too much, or do you have sort of like a written checklist where you just know? Okay, if I've done three international trips within a month. Okay, that's it. Do you have a rule like that or is it. Do you just listen to your body?
[00:32:43] Speaker A: Yeah, I don't really have a fixed rule per se, but I mean, leading up to it, I mean, I'm just like looking now at my, in my schedule, like I had been just traveling so much. We had, we had just come back from, you know, from a trip. I would have, I would have been home two days and then, you know, and then back on the, on the road. And so it just like when you look at your own calendar and you're like, oh, God, that's, that's not that's not a good feeling.
And so I think, I think a part of it is listening to your gut. And by gut, I mean, you know, we, we all know by now, right, that, you know, so fascinating that your, your microbiome, your stomach literally has dopamine. It has serotonin. It is your second brain. And so listening to your gut is essentially listening to your body's warning signals to you that are coming to you in such a way that they are not overridden yet by your prefrontal cortex. You know, my prefrontal cortex might have said, oh, but you can do it physically. You can do it like, you know, schedule wise, that's hard, but it's doable or whatever.
But my body was just like, oh, that's, that's like very poor decision making. So I, I tried to. I tried to listen.
[00:34:05] Speaker B: Yeah. Cause in, in the book the Long Game, you talk about how in the old days, you know, you might get in a cab and go across town for a coffee and then take a cab home, and it's like three hours have gone by.
So what do you say no to now that you would have said yes to 10 years ago?
[00:34:19] Speaker A: Certainly when it comes to fees and things like that, I mean, you have to continually update the floor on your fees. And, you know, you might make a thing that I certainly did 10 years ago was, even for things that were unpaid, I would make exceptions because I thought it was good exposure or it was just like a box you wanted to tick. Like, I think about something like, you know, speaking at south by Southwest, right? Like, that is a thing that is unpaid. I mean, maybe they pay like the big, big keynoters, I don't know. But certainly they don't pay the smaller presenters.
And I've spoken there a couple of times and like, that was so cool. Like, you know, I had grown up hearing about south by Southwest. I'm like, oh, this is awesome. You know, you get to go to Austin and you get to be part of this big conference and, you know, it's sort of a, a neat status thing, but, you know, you do something once or twice and then it's like, okay, well, that was cool. But, you know, it's on the resume. I've done it once. I'm not sure what the marginal gain is of doing it again. And, you know, you speak to whatever. I mean, you know, it's different maybe if you're, if you're on the super main stage, but I mean, if you're, you know, in a breakout room and you're speaking to 100 or 200 people. That's awesome. But you could also be on a podcast from your living room and you know, 200 people are going to listen to this podcast. More. Well, more than 200 people are going to listen to this podcast. And I've saved myself like, you know, hours and hours of travel and, and now, you know, air traffic is so messed up. It's like, okay, great, there's like a four hour flight to there and back, but also it's probably going to be delayed two hours on either side. Like, you know, there's like all of these switching costs and maybe at a certain point it's worth it to see people, but if there's other ways you can see them, it becomes a long run for a short slide. And those are the things that are absolutely worth doing early in your career because you're getting the momentum, you're getting the social proof. It's like, great, I want to meet everyone. I want to see everyone. Like in the early days, like, it is an amazing decision to do as much as you humanly can with as many people as you humanly can to get the snowball rolling.
But then you have to sort of just take a step back and have some discretion about it because it's like, well, what are you spending your time on? What is proactive versus reactive? What do you actually want to accomplish? So it's like that for me for speaking engagements, for conferences, or, you know, things like that, or, you know, sometimes favors for people. Like, you know, you just have to think like, okay, what is it going to entail? I got an email from somebody yesterday who is, is lovely, who, you know, is a person who's like a reader of my work and they're working on a book and they wanted to know would I like to contribute something for the book. And the truth is, if it was like an endorsement quote or something where I could be helpful kind of fast, I would, I would be like, sure. But I, I looked at this and it was like, would you like to write an 800 word sidebar? And I thought, okay, if I'm going to do that, right, that's going to take at least an hour. Maybe it's two hours. Like just, you know, if, if it was something where I thought a hundred thousand people are going to buy this book and read it, perhaps that is worth it.
But that's not the case. And so if I can be helpful in a fast way, I want to do it. If I am dedicating two hours of My life to do something, it either needs to be like, my best friend, or it. It just. The ROI calculation is. Is not there. So maybe there's a different way that I can route my help, if that makes sense. I don't know. What are you saying no to now that you didn't used to?
[00:38:00] Speaker B: Diana, in the long game, you talk about your calendar. I look at my calendar. I've started to block off everything to be realistic.
[00:38:07] Speaker A: I mean, you're a person who has a lot going on. You've got your. Is it jiu jitsu, or what's your judo?
[00:38:13] Speaker B: Karate, Karate.
[00:38:15] Speaker A: I know they're all the same in my head, although I know they're all very different.
[00:38:19] Speaker B: Yeah, I train at least an hour a day.
[00:38:21] Speaker A: Oh, my God, you're so good.
[00:38:23] Speaker B: Actually, I trained here in the hotel today. It was really fun.
[00:38:26] Speaker A: That's cool.
[00:38:27] Speaker B: Like, it was a little bit embarrassing. Cause I was in the. In. In the lawn, like, in front of. I think people could see me. Yeah. So there's that, but there's. You know, I run the foundation. I. I coach a few people and I run. I do this podcast, and I. I'm also writing a blog, although I've now alternated. One week podcast, one week blog, one week podcast. Because it's just doing two in one week is too much. So I'm sure there's some other things, too. Running. Running different households across the world. That's enough, right?
[00:38:51] Speaker A: Oh, my God. That sounds like enough.
[00:38:53] Speaker B: Yeah. The calendar is a good look. Like when you talked about the travel thing. Looking at your calendar and going, how could I physically do this?
What's another rule that I use?
Well, if it doesn't fit one of my five goals.
[00:39:06] Speaker A: Yeah. What are the five goals now?
[00:39:08] Speaker B: Aha. Look at you coaching me.
Well, I'm working on a new book.
[00:39:15] Speaker A: Mazel.
[00:39:16] Speaker B: Yeah. And it's not a memoir. I have written a memoir, but I just don't have the courage to publish it. And so now I'm doing a book about wealth and wellness and the intersection of both.
[00:39:26] Speaker A: That sounds really interesting.
[00:39:27] Speaker B: Using some of my own personal experience, but also drawing in some research out there from people like you and people like doctors and people who are successful. But it sometimes can come at a cost. I know somebody who became a type 1 diabetic because he worked so hard, and he.
He just didn't take care of himself during, you know, the building out of his business. I think we can have limits in our business. We can have also limits having to do with health. And I think you know, you not traveling because you know you're going to get sick is one of those limits. Seth Godin doesn't travel at all.
[00:40:00] Speaker A: Yeah, I know. Smart man. That's great. I mean, I can totally relate to that. When I, you know, around the time that I launched the Long Game, I mean, my schedule was. It was punishing. I was doing like sometimes up to nine podcast interviews in a day.
I mean, that was, that was the exception. But it was not uncommon for me to be like five or six in a day. Like, it was, it was ludicrous. And there was just so, so much work and so many calls and so many interviews and meetings to try to launch this. And, you know, I mean, on the bright side, like, it works the way that I wanted it to. Like, it became a bestseller. It was on the bestseller list for a couple of weeks in a row. And, you know, it got. It got early traction, which is what I wanted.
On the downside, I think it, it, you know, it like really messed up my health for, for quite a while. And I ended up, you know, getting diagnosed with high blood pressure. And, you know, that's something that I have, like, in my family. So it was not crazy, but like, you know, it's the kind of thing that you wouldn't be surprised if it sort of manifested when you were in your 60s. But I think that my behavior honestly probably brought that on early because I was having so much stress and I just didn't know how to offload it. So I've spent the last couple of years, like, really trying to work on that consciously to try to see if I can improve and get back to healthy levels. Nice.
[00:41:24] Speaker B: I'm so glad that you're working on that because it's. We gotta keep you around, Dory.
[00:41:29] Speaker A: That's right. That's right.
[00:41:31] Speaker B: So the other goals I have have to do with. I'm working on my third degree black belt in karate because I've started teaching. Actually I'm teaching at Selvae Regina University.
[00:41:41] Speaker A: Wow.
[00:41:41] Speaker B: Teaching at the YMCA in Newport. Total beginner.
[00:41:44] Speaker A: This is incredible, Diana.
[00:41:45] Speaker B: Wow.
Initially it was selfish because I don't. There's no dojo in Newport right now, so I had to create it. And with the blessing of my sensei, he's like, okay. Teaching beginners. So I boped back and forth between New York and Newport.
[00:41:57] Speaker A: That's. That's so cool. Have we ever talked about my illustrious martial arts background?
[00:42:02] Speaker B: No.
[00:42:03] Speaker A: You know, when I was a kid, I did taekwondo and it's my little embarrassing chapter. I Got up to a yellow belt, green stripe and then I quit because we, that was the place where you started sparring and I, I was nervous and didn't want to hurt anyone, so I quit.
[00:42:24] Speaker B: This kind hearted person.
[00:42:26] Speaker A: I was not cut out necessarily for martial arts greatness, but I, but I very much respect what you're doing. I think that's super cool.
[00:42:32] Speaker B: Well, thank you. Well, it's part of, it's part service and it's part selfish. It's, it's, it sort of ticks off a lot of the spiritual, you know, the, the physical.
[00:42:41] Speaker A: Yeah. So cool.
[00:42:42] Speaker B: Yeah, it's super cool. What else am I working on? Well, I, I'm hoping to get a few million downloads on this podcast eventually, so.
[00:42:49] Speaker A: Yes, yes. Grow this sucker. I love it.
[00:42:52] Speaker B: And of course I'm, I'm working on building the, the coaching business. I'm not looking for huge numbers and I only want to work with three or four people at a time. No more. But I've got a few right now. I've got a wonderful group of entrepreneurs in recovery.
[00:43:04] Speaker A: Mm, interesting. That's nice. Yeah.
[00:43:06] Speaker B: So they all have 12 step as their language, but they are all looking to build a business. So our topic is mostly about that health and fitness goals come into.
So some of them want to quit smoking now. The other, some guys are looking to get, you know, in the gym and start working out.
[00:43:22] Speaker A: You're such a perfect coach for, for that. That's, that's like such a good way of getting right in your wheelhouse.
[00:43:28] Speaker B: Thank you. Right before coming here, I did the, I did an hour of karate with my sensei and I feel so great.
I feel like my synapses are working better thanks to the movement I just had.
[00:43:40] Speaker A: I'm sure that's literally true.
[00:43:42] Speaker B: Yeah, yeah, I know we're getting to the top of the hour and I, I didn't want to leave you without asking you about your musical theater. I wanted to know like, how does music writing, musicals teach you anything about writing business books, if anything?
[00:43:57] Speaker A: So, yes, I, I am working on three different shows and as a matter of fact, as we are recording this, this interview tonight, I am going to be participating in a pitch night competition. And it's very exciting. There's an organization called musicalwriters.com and maybe once or twice a year they have, they have their annual pitch night. My show has been selected as a finalist. So I get to do a five minute Shark Tank style pitch for it. And the winner of the competition gets their show, you know, produced for like A reading in Dallas, Texas. So that is always a really exciting thing. Unlike for writing a book where it's like you write the book and then you can, you can read the book and you can see if it's good or you can give it to a friend and see if it's good for a musical. You can kind of imagine what it's going to be, but you actually can't really tell if it's good or you can't really tell if there's problems with it or unless you get like a dozen people to put on your show and like, so you can see it and hear it and that takes quite a degree of coordination. So it is a big deal to get a reading of your show because it helps you see things in a way that you wouldn't otherwise. So wish me luck. I'm working on that. About six weeks ago in New York City, we did a one night performance of another of my shows called Absolute Zero. And that was at a club called 54 Below, which is a kind of Off Broadway, Broadway staple. Amusingly, it's called 54 below because it is directly underneath what used to be Studio 54. So that's kind of its fun claim to fame, but we had a couple of Tony nominated actors who were starring in it and it was a really cool evening that sold out. So a lot of good things happening.
[00:45:36] Speaker B: Oh my God, I've got to come to one of your shows.
[00:45:38] Speaker A: Yeah, yeah, next time for sure.
[00:45:40] Speaker B: That's so cool. So what else are you working on right now?
[00:45:44] Speaker A: Well, I, I, I can't sort of talk about it yet in detail because it's like in process. But I do have a new book that I am working on with a couple of co authors and it is, it is in process, it is actually out now with, with a publisher and we're, you know, beginning, beginning the process of shopping it around and figuring out how and where we want to publish it. So I am hopeful that by the end of the year I will have an announcement to make. So God willing. Good.
[00:46:15] Speaker B: Can you give us a hint about what it's about?
[00:46:17] Speaker A: It is about coaching actually. So I think it will be hopefully relevant to you. So I will, I will be sure to let you know asap.
[00:46:26] Speaker B: Oh, that's so cool.
[00:46:27] Speaker A: Yeah, thank you. I'm excited.
[00:46:30] Speaker B: What do you wish someone had told you 10 years ago?
[00:46:32] Speaker A: What would have been most helpful, you know, to bring it full circle from where we started is don't worry, you'll, you'll meet your wife on November 15th, 2022. That would be really helpful knowledge because half the problem with being single is just like, oh, my God, is this ever going to end? And so I, I think it would have been comforting existentially to know, like, okay, just be patient, like, all things right. You teach what you want to learn. And so I wrote the Long Game because I have always been deeply frustrated with the concept of patience. I do not like it one bit. And so I have had to write this book so that I can, you know, make my peace with it.
[00:47:16] Speaker B: Well, that's one of my character defects is impatience.
[00:47:21] Speaker A: I mean, strengths probably and defect, right?
[00:47:24] Speaker B: Yeah, it's both. That's the whole thing is that all these character defects actually have a plus and a minus side to it. Yeah, we get things done, right?
[00:47:31] Speaker A: Amen. Amen.
[00:47:33] Speaker B: Are you still using paper for your lists?
[00:47:36] Speaker A: I do.
It's over yonder on the couch. But yes, I do. I have my little yellow legal pad. I like having a paper thing. I mean, my calendar is electronic because I like to be able to access it whenever I need it.
But no, I have my to do list and it is, in fact on paper. That's right.
[00:47:54] Speaker B: But have you tried any digital tools and then given up or did you just stay with paper?
[00:47:59] Speaker A: I mean, you know, I, I know that there's a lot of, a lot of good things out there. Like working with my, with my chief of staff, for instance. Like, we have a shared Google Doc and like, we go back and forth on the Google Doc with, with stuff. I, I think I'm kind of in, like, if it ain't broke, don't fix it mode. It's not burdensome for me to, like, carry a little light notebook with me when I go on a trip or something. And it's also not like, if I go out for the day that I am like, oh my God, I'm so lost without my to do list. Like, if there's a thing that I need to add to it, I will just send myself a reminder and then I will add it. Like, so it's, it's not, it's not problematic, but there is something satisfying I think about, you know, like the, the crossing off with an actual pen. Yeah, exactly.
[00:48:44] Speaker B: When you're walking around, do you use Siri? Like, Siri remind me, right?
[00:48:49] Speaker A: I have Siri turned off because I, I, I continue to think it's creepy, it's irrational, because my wife has Siri, so her Siri is listening to every fucking thing I say. So. But I don't want my Siri to be listening, so I have it turned off.
[00:49:03] Speaker B: Oh, that is so funny.
It is. It's. They're listening all the time, aren't they?
[00:49:09] Speaker A: I mean, it's. It's. It's, like, weird. Yeah. Like, you get these stories, and I understand they're, like, the freak outlier stories, but, you know, you get instances where it has recorded things that it really clearly should not have recorded, you know, and. And you read those reports, and it's like, oh, this is not as foolproof or as airtight as one might like to imagine, so eventually, we're going to have to give up the ghost on all privacy and, like. Okay, you know, I understand, but I'm hanging on to what I can while I can.
[00:49:40] Speaker B: I love that.
Well, thank you, Dorie. I don't want to take more than an hour. I promise. An hour. And I think we've got it.
[00:49:48] Speaker A: Diana, it is always a joy to get to talk with you. Thanks for having me on, and congrats on your show.
[00:49:53] Speaker B: Oh, thank you, Dorian. I'm so honored that you came on and said yes, of course.
And I hope to see you in New York or in Newport, if you.
[00:50:05] Speaker A: Ever want to come up, or Miami, if you want to come on down. All right. Thanks, my friend.
[00:50:10] Speaker B: Bye. Thank you. Bye. Bye.
