Rachel Hollis on Empathy and Emotional Acceptance

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1:17Learn more at toyota.com slash trucks slash adventure dash detours. That's toyota.com slash trucks slash adventure dash detours.

1:32Welcome to the Daily Stoic Podcast, where each weekday we bring you a meditation inspired by the ancient Stoics, a short passage of ancient wisdom designed to help you find strength and insight here in everyday life. And on Wednesdays, we talk to some of our fellow students of ancient philosophy, well-known and obscure, fascinating and powerful. With them, we discuss the strategies and habits that have helped them become who they are and also to find peace and wisdom in their actual lives. But first, we've got a quick message from one of our sponsors.

2:19Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. I got an email a few weeks ago from someone whose work I was familiar with. I'm familiar with their work because their work has sold millions and millions and millions of copies. I'm familiar with her because she lives in Austin. And we had never chatted before, but I had talked to her ex-husband before he'd asked me to blurb one of his books. And they lived out in the hill country, which is not far, but I'm a bit of a homebody, so I'd never ventured out there. And she sent me a nice note about how she'd read The Obstacles the Way, and it had been very helpful to her.

3:08and it was just a very nice note. And she said, hey, would you want to come do the podcast sometime? And I said, you know what, let me think about it. I've been doing a lot of interviews lately and not sure I have the bandwidth. And then I saw in the news that her ex-husband had just suddenly died, which was a sobering reminder of memento mori, as the Stokes talk about, that you never know. putting off meeting people or seeing them or, oh yeah, it's been a while. Like you never know. You just, you never know. And as my interview with Bozama St. John was talking about recently, the urgent life, you know, in light of death, a lot of petty differences or resentments or fear, all the things that can get in the way of relationships, it sort of falls away.

4:11And that was something I imagine today's guest was thinking about or wrestling with when someone, even if you're no longer with them, certainly no longer with us. And so I sent her a note and I said, Hey, I hope you're doing all right. And then I said, you know what, what if we, cause she had talked about maybe coming out to the bookstore. I said, what if you came out and we just had a long conversation? We interviewed each other or nobody was interviewing anyone. We just had a conversation and maybe we got two podcast episodes out of it. And so that's what we did. It was a wonderful conversation.

4:46And part one of That's going to be here on the Daily Stoic podcast. And part two of it will be over on Rachel Hollis' podcast. She came, we did it in the new Daily Stoic studio. She signed some books over at the Painted Porch. Her massive bestsellers, didn't see that coming. Girl, stop apologizing. And girl, wash your face. You have seen in every airport you've ever been into, one of them sold four and a half million copies. So it's just a monster book. and she's a huge influencer and guru and role model for women and entrepreneurs and mothers all over the world. She's a huge lifestyle brand and media company, but like all of us, she's also a human being and she made some mistakes and there was some controversy and there was some backlash.

5:37You might say there was some cancel culture involved and all of that made my guest today, Rachel Hollis, reconsider a bunch of things, reconstitute her life, her priorities, her perspective. And I think that comes across in today's interview. She was wonderful to talk to. And I do find, as always, that the more controversial a person is in the news, with some exception, the more controversial that person is, the more preconceived notions you are, the more surprised you are at how nice and reasonable and human the person you sit across from ultimately is, which is why it's always something I recommend.

6:22I think you're going to like this interview with Rachel Hollis. And like I said, if you enjoy it up through the end, we'll just go over to her podcast. I'll link to that in today's show notes and you can finish the episode. We totally lost track of time. We talked so much longer than we thought, but I think it was totally worth it. So you can follow her on Instagram at Miss Rachel Hollis. You can go to her website at Miss Rachel Hollis, and you can check out her books. Didn't see that coming. Girl, Stop Apologizing. Girl, Wash Your Face, among others. That's only three of the nine. She's written a ton of other books, which is something we talk about.

7:00You know, we always think there are these overnight successes, but people, there's way more prologue to most of the people that you have heard of. And that's what we talk about in today's episode.

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9:48All right, well, where should we start? Wherever. I usually just chat about anything. Let's start with, is that a real Grammy? That is a real-ish Grammy. I did win a Grammy. Stop. For what? So some authors win them for reading your audio book. I know. It's my only chance at an EGOT. It was certainly one of what I thought was my only chance. But no, a friend of mine produced a jazz album. And he was like, hey, I need help with the liner notes and writing all the stuff. And so I helped him with that. It was an instrumental jazz album, which I know literally nothing about. I just helped him with the liner notes.

10:25And then. What are liner notes? Like the, you know, like in a, remember CDs? Like all the text that would come with the thing. There's this cool album. It's called Presidential Suite. And it's a bunch of the great presidential speeches of all time set to jazz music. Cool. So there's like writing involved and like how that. Anyways, I worked on that. So I was a producer on the album with like 20 other producers. And then Grammys are actually about as – I came to understand the Grammys are about as political and insidery as the bestseller list. A hundred percent. Except for the bestseller list is to a certain degree just like here's who sold the most copies and then here's who we chose among the ones.

11:13Yeah. This is like this process of voters. So like you campaign to be nominated and then you campaign to win. So anyways, there was this whole campaign to do it. And then we ended up getting nominated and then winning. So I'm a producer on a Grammy award winning album. But I did get to go on stage and accept a Grammy at the Grammys. What year was this? This was 16 or – no, this is 2017. And so two things I learned. Number one is there's actually two Grammys. There's the Grammys that you see on TV, which like Adele wins or Kanye, you know, steals it from Taylor Swift or whatever. There's that, which I also attended.

11:57They give out like 10 Grammys at the Grammy Awards that are at the Staples Center. And then there's another theater next to the Staples Center called the Nokia Theater. That's what it was then. and that's where they give out like hundreds or thousands of grammys for like best women's country album with harmonica like all these categories that you would never have thought of existing but are music right like who do they give best album cover design to they don't do that on tv it's best heavy they they haven't announced best heavy metal album on tv on the tv grammys for 30 years, but that's still a real category.

12:36So there was that. There was like 50 people in the audience and we just went up one after another and accepted our Grammys. And then the other funny thing was they only give one Grammy. Yes. This is what I'm wondering. Do you like file a petition later? So they were like, if, you know, one of you gets to keep the Grammy and there was like 20 of us. And then they were like, the rest of you can fill out this form and they'll send you like, we'll send you like a certificate and i was like fuck that yeah i'm gonna make my own grammy which i did uh because it's just you know like any other trophy and then i just wrote um uh so it says ryan holiday uh best large jazz ensemble album 2017 and then i wrote uh when you die this will go in the trash alongside all your other accomplishments so that's my grant i love that yeah i this is the first time that i thought oh there's a way like if you touch something you can file for it's like a super bowl ring like you can also get it but you personally made that yes and actually i also got uh i have not a super bowl ring but i worked with i worked with the rams uh and they sent me like so all the players get a ring right that are on the team and then there's like the the outer circle of people who get like who can get a ring like they probably give one like um uh i remember i was riding one time in the elevator at a spurs game and uh the elevator guy had a a championship and i said how did you get that and they were like he was like the spurs are the greatest organization in the world they gave a ring to every single person who worked for the team that's so rad which is like how you get the culture of like a championship organization so anyway there's that ring and then there's an out then there's an outer circle beyond that where they're like, you were nice or like, we like your stuff.

14:25And they gave me like a giant novelty. Do you wear it? No, no, no. It's like a paperweight version of the Super Bowl ring. Oh, okay. Well, I mean, you could still wear that. So I don't have a Super Bowl ring, but I have a novelty like participation Super Bowl. It sounds like a theme. Yes. I should put it here also. What a life you've had. It's been weird. It's certainly not what you think when, like, I don't know about you, but you're like, I want to write about X. And then you're like, maybe it'll do this. And then whatever, it would be preposterous to have assumed that X plus all these other things would happen.

15:05A hundred percent. And you'd have to have been a deranged egomaniac to think that even that was in the realm of possibility, which is actually something I really don't like about success stories, is I think people very disingenuously, like it's not even they take credit for it, but they act as if that was the plan all along, which I think is very intimidating to people who would not only relate more, but be more inspired if they knew that like, actually you're just trying to do this one thing and that set in motion all these other things. Right. And so like, yeah, like I wanted to write a book about ancient philosophy and then I'm getting a Grammy or a novelty Super Bowl ring.

15:48To have thought that those things were connected would have been a preposterous ability to see in the future and an entitlement too. Do you know what I mean? Yeah. Well, I think the more I do this work of interviewing people, the more I find this through line in that it doesn't matter what they do, whether it's an actor or a writer or athlete, it always to me sounds like they're really interested in something. They started working toward a goal that they had. But along the way, when opportunity was presented, they were like, yeah, I'll try. I'll sort of see where this goes. Nobody has ever sat down.

16:27I don't know if you find this too. It's never a linear path. It's always like, I went here and then I went here and then I did a backflip and then I ended up over in this place because I think we all could have an idea of where we want to end up. And if you're too rigid about it needing to be that exact thing, you're going to, I don't know, I feel like I would have failed too much to keep going. Well, I think that's true. And then the other thing that happens is then afterwards we go actually know that this is what I was trying to do the whole time. And then we don't actually realize how that closes doors in the future.

16:57Like an ego and the enemy, ego is the enemy. I was telling the story about Google, like Google starts as like a PhD thesis and then like they thought maybe it would work as a company and then it became this thing. YouTube was like a dating app that turned into a video thing that people thought was a terrible acquisition. Gmail was this small internal, like all their big things were actually somewhat accidental or serendipitous or just started small and became something huge. So for Google to then go like, no, we're this world changing group of visionaries who like conceive vastly into the future.

17:34That actually makes you make worse decisions in the present because you have given yourself a kind of site that you don't have. And you've also given yourself like some sense of your capacity or your genius that's also not there. If you said, hey, we're a company that takes little bets and some of those bets work and some of those don't, that's actually what you should continue doing in the future. That's a recipe for success. If you're like, no, no, no, we're the visionaries who can predict the future, then you're like, oh, let's spend a billion dollars on Google Glass or let's spend a billion dollars on this.

18:10And then you're like stunned when it doesn't work. Those ideas might've been good actually, but if you'd started smaller and been less arrogant or utopian about it, you might've actually done better. And so like I try to, like I thought I was gonna write a book about ancient philosophy that would matter to people in business. And then it ended up resonating all these different, but I try to go back and go like, I really had no idea. And I try to remember that I don't have really any idea. So then when I'm sitting down to doing the next book, I'm like, I hope it'll do this. I'm not like, I know exactly what everyone wants and I'm always right.

18:52Yeah. I think that we, especially as creators, if you are working with that end goal in mind, I feel like you're playing to whatever you believe the trends are, which never works. So after Girl, Wash Your Face explodes and all of a sudden it's, everyone's like, how did you, I'm sure they did the same thing to you. Like, how did you do this? How did you know? I'm like, I have no idea. I literally just did what I was always doing. And for some reason at that exact moment in time, it was the right place, right time. And it exploded. And I don't ever believe that's possible for me again. If it happens, amazing, but I'm not betting on that.

19:30I just sort of kept showing up, kept doing the work, which is, I think, what a lot of authors do. We plug away and you know us for one or two pieces when really there were 50 others that you've never heard of or cared about. Well, isn't that like, that's, I think, something people miss from yours is they think that that was your first book, but it was not even close. No, it was my sixth. Okay. So that's, but that's a radically different story, right? It's like a woman writes a book and it blows up and now she's this huge author. It's very different than a woman writes five books. They all do not enough that you even know about them.

20:08And then the sixth one blows up. Like one is, first off, a much more relatable story. One's a much more honest story. And one also actually asks a lot more of people, right? It's like you think, everyone thinks their first book is going to crush or their first thing is going to crush. And it does for 1 % of people, but for the vast majority of people, it's a much longer, slower burn than that. I always feel worried for anyone who has a success on their first go, whether it's a musical artist or someone who goes viral because you believe that that's the path. You didn't have to like crawl through the desert.

20:52You didn't have to keep going when nobody cared, when nobody came to your book signing. you don't sort of have that muscle. And so when inevitably you put something out and it doesn't work, I feel like that ends up being your end. Well, that happens on social media, I think even more because like it's hard to do a book and it's hard to do a book. Ultimately, if your book succeeds, it has something in it that like people thought was worth purchasing with money, which is a pretty high thing to get over. Whereas like if you're someone that suddenly has a lot of social media followers, some of those people are talented, But it's also very possible to not be talented, right?

21:27And so if you're someone who was, let's say, on a social network early and you blew up there, you can tell yourself this story that you blew up because you're super talented, you do all this amazing stuff, whatever. And what this is actually preventing you from is developing any sort of objective base of skills or competency that will work in other mediums. I was talking to my son about this who's just starting jujitsu. And I was like, it's actually good that you're smaller and younger than all the other kids in the class because you're going to have to actually figure out how to get good at it.

22:04Yeah. Whereas if you were bigger and stronger and heavier, you would be able to coast on just your natural advantages or the mismatch. And I think that happens on social media a lot where people were the – one of the early people on TikTok now they have millions of followers. They don't – there's no there there. because they were just gifted a huge audience. And I'm not jealous. I'm just saying that that's going to be hard to translate to the other things that you want to do because you're not learning how to do a thing. Yeah. How, like, what are your thoughts on social today? Because, forgive me if I'm wrong, but you come from a marketing background.

22:44I actually think the first book I read of yours was a marketing book, right? It wasn't maybe social media. Like it wasn't stoicism at all. No. I mean, I wrote like a critique of online marketing in 2011. Yeah, which I probably read. I've been doing this a long time. Yeah, I do have a marketing background and I do think all the platforms are important and you have to figure out how they work and how to spread your ideas on them. There are very few people who are not sort of legacy acts that can just only do their thing, right? Right. That, and if you think you're one of those people, you're probably not one of those people, right?

23:25Very few people get to be Cormac McCarthy who write, you know, a novel every 30 years. It's world news and they don't do a single promotional thing for it. And it's just huge. Like that's, that's not happening anymore. That's gone. So I think you have to figure out all the platforms and you have to spread your work on them. And this is where people discover things. That being said, you have to find a way, I think, to create as much distance between you, the person, and those platforms if you want to remain good at what you do. What does your relationship with social look like? Like day to day, are you actually doing it or someone else does it for you?

24:05Someone else is doing it. I don't even have any of the apps like on my phone. Oh, wow. So you don't consume it at all? I mean, I do like I my wife and I watch Instagram reels and like we I am on it as a regular person sometimes. But I have no access to being me on the platforms. Do you ever worry about that? What do you mean? That someone else posts on your behalf says the wrong thing. Yeah, I guess. And then you get in trouble, even though it wasn't you. I approve most of the stuff like I make the stuff. But I don't – I'm not like give me the likes. You know, like it's not going into my brain.

24:50Right. And I think that's the – like I've just – you know what audience capture is? So audience capture – I mean there's different ways to think about it. But this happens most often like politically. Like someone will take some sort of like controversial stand, right? Like it's maybe right wing or left wing. and then a bunch of people will not like them for that thing and then a bunch of people will like them for that thing. And then the people that like them for that thing, those are their people now. Okay. So they just tell those people what's happening over and over. Russell Brand is a great example of this.

25:25Like Russell Brand went from this like funny comedian to this sort of enlightened spiritual guy to a straight up crazy person, conspiracy theorist. Like he posted a picture of him and Donald Trump Jr. the other day. You're like, whoa, how did you get from here to there? And you're like, oh, the algorithm took you by the hand and guided you over there, especially if you're somewhat skeptical or contrarian or if you have some sort of grudge. Like if you've been put on the outside a little bit, you go, this is the only place. Like I think naturally as a creator, if you're not careful, you go to where there is traction or heat, right?

26:06And so you just end up playing in a space and at a certain point that just becomes who you are. Well, my new thing, and this has been the most freeing decision I have made. I have been on social since the beginning. Yeah, sure. Like everybody, right? I had a blog and so I would post and like little recipes, whatever. About a month ago, I made the decision to no longer allow comments and no longer see like counts. And I had, I don't post that often. I posted more to talk about the podcast. Like when I'm really proud of the work, we have a great guest, Ryan Holiday's on, holy crap, you guys. I will post about that.

26:47But above and beyond, I found that I am a better creator. I'm a better human, better mom centered, all the things that we want to be when I am not on that. And I won't allow anyone else to post on my behalf. So if I want to talk about my work, it has to be me. That being said, I know there's such opposing opinions on this. But for me, I'm just tired of giving my platform to people in comments who are just, it's bananas. They're not even writing about me. They're just writing crazy stuff or they're fighting with other people or whatever. So I made this decision. I'm like, I'm just not going to allow comments anymore.

27:27And it's the most freeing thing because I don't care how the post does. I have not cared about that in forever. But it allows me to show up as myself, messy, real. Here's this thing. If you like it, great. And if you don't, that is fine too. But I just don't want to buy into this idea because I am not struggling. If I see something like, oh, hell, they liked that outfit. Got to do more outfit of the day posts. And I don't want to create in that way.

28:04You hear that? That's not just a Toyota truck. That's the sound of no crowds. No alerts. No distractions. And no telling what you'll find next. You know, like a detour. So why would you ever take a tour when you could take a detour? Toyota Trucks. thanks to toyota trucks for sponsoring this episode when i bought my ranch in 2015 out here in basco county i drove my car about halfway down the dirt road that we live on thought this isn't going to work stopped parked it walked the rest of the way home borrowed my wife's car drove in austin and bought a truck what i bought was a toyota tacoma and this truck wasn't just transportation, getting me to and from my house.

28:58It unlocked a whole different style of living for us, not just on the ranch, but in our little Texas towns. There were places I could go now that I couldn't go before, especially out here in the piney forests, through the fields, and on the unpaved roads like the one that I lived in. We got to go deep into the hill country's wild beauty. We've driven all the way out to East Texas. We've driven across the country. And by we, I mean not just my wife, but both my kids who I drove home from the hospital in that truck. Toyota trucks are built for those who understand that the best adventures happen when you're willing to veer off course.

29:38Because you never know when you'll end up on a Toyota adventure detour. And of course, this is stoicism too, because every detour, every obstacle is an opportunity. But it's helpful if you can handle the difficulty inherent in that. If you've got the resilience and the right companion to make it wherever the road takes you. Discover your uncharted territory. Learn more at toyota.com slash trucks slash adventure dash detours.

30:09Yeah, I think it's not healthy data. It's not things you would want to know, but you can get really granular data on it. It's better not to know. So for the Daily Stoic, I send out an email every day to 600 ,000 people. And I send another. So I do two emails. I do Daily Dab, which is 600. And Daily Stoic, which is like 600. And Daily Dab, which is like 100. So every day I write this thing. And it's an email. So you can reply to the email. Oh, wow. And I had to make a pretty conscious decision relatively early because the numbers started small, but they got big quickly. I had to make this decision basically like, do I want these people to have direct access back to me or is this a one-way conversation?

30:58and I just found that knowing what people thought of it did not make me better at doing it it did not make me happier as a person and actually it made me it made me less likely to say what I actually thought or what I thought was important because no like it's not healthy for a creator to know, hey, this thing that you just wrote about that you thought was important or heartfelt, it just cost you X amount of money because this many people left, this many people unsubscribed, this many people told you they would never buy something from you again. And I wanted to write without fear or favor. And you can't do that if you're bombarded with data in that way.

31:49And so I've decided not to have that information. Does it mean sometimes I might get something more wrong that like I might have gotten sure, but it mostly makes me able to just say what I think. I think the question for every creator is like, do you own the audience or does the audience own you? Oh, shit. And I think algorithmically and when you're looking at the data, it's very easy for the audience to own you because you're trying to like surf this wave. And sometimes like people, they'll manage and I can tell it's like, oh, man, I must have gotten a lot of negative emails about this because they found my actual email and they forwarded me today's email and are commenting.

32:33And I can see that they emailed this address and it didn't work and this address. They were knocking on all these different doors until they found the one that I was in to be like, listen here, you piece of shit. That's what they did. Do you ever think if you applied this energy to your own life, to your own – if you hate my content, go make what you think is good. Go put it out into the world. Like if you just applied your hatred of someone to your own life or your own work, I just feel like everything would explode for you in the most positive way. Well, the funny thing is it's almost never something I said.

33:13It's something that they heard. Right. It's like I didn't come out and say all these people are criminals and deserve to be in jail. It's like I made an offhanded remark and they inferred this thing. Clearly, they already feel like guilty or whatever. But I'll get those and I just think, wow, if I had gotten 500 of these, that would have had the effect of intimidating me. Debilitating. I think what you also realize like really crazy people is like the point is to raise the cost just enough on the person to make them go, this is not worth it. And so I try to keep that space because I think it's really – and sometimes when they do, they're like, why did you have to say this?

34:02Didn't you know you would piss off this person? Offend this specific person. And I say something like, look, I didn't get – I didn't work really hard to build up this audience to then not say what I think. And that's kind of how I think about it from a career perspective is like the purpose of succeeding as a writer of getting to some means of financial independence or security or confidence or whatever it is, it should not be to then be terrified of losing it. So you are not yourself. When you say, you know, the idea of like, it's not what I said, it's what they heard. Yes. It reminds me of this thing that I have chewed on and processed for years now, which is apologizing for the impact versus the actual intent.

34:54Yes. So, or the idea that your intent can have a very different impact than you intended, right? Totally. But then I had always sort of been taught that coming up in building a business through social media was you have to apologize for the impact. Yes. But then at the same time, somewhere along the way, I started taking the impact and flipping it and believing that that was my intent when it wasn't. so allowing someone else to say well i was offended when you said this and i'm such a people pleaser by nature and such a good girl that i'm like holy shit i have a fin and i i can't believe i've done this i can't and it took a lot of therapy to get to the other side and come back to wait a minute that wasn't what i was saying that that actually isn't even what i said but i've been taught to apologize for what you heard.

35:50And at some point then, as a writer, as a creator, I have lost my voice because I'm too afraid to talk about anything. Well, I think, so I have two thoughts here. So number one is, I think something that people get wrong about stoicism is like, stoicism is like, focus on what you control. You don't control other people. So if you offend someone, it's like their problem, right? This is like, I think a very male take on stoicism that I dislike, right? Like going around not giving a shit about other people or the consequences of your actions or the impact of your words, that's not cool, right? And so I think some people, like there might be some take on stoicism where like political correctness is bullshit.

36:34Like don't worry about these snowflakes. Just do whatever, do and say whatever you think. I think that's totally missing it because I don't want to hurt people's feelings. Same. And I actively try not to hurt people's feelings. I don't build my entire life around not doing it, but I do try to take it into account. And if someone comes to me and says, I've been negatively affected by something you did or said, I take that and I go, well, was that, did I mean to do that? How is this, is what I said important to me? And if it's not important to me, then I'm definitely going to be very quick to apologize because it was not only unintentional, but like I was just being thoughtless and you've actually helped me to be a bit more thoughtful about that thing.

37:21So I'm going to take that. But I think what you're saying that is important is that just because you made someone feel shitty doesn't mean that you are a piece of shit. Yes. Because there could be so many things between you and them that contributed to that ultimate feeling that you can't possibly put on yourself. And so I think it's a balance. It's like someone gets upset. You're like, you know, sometimes, again, I'll just thrown off something offhand. I didn't really think about who's on the other side of this. and now that I have thought about it, I don't like that I said it and I won't say it in the future.

37:56There's other times where I said what I said and I mean it and if that offends you, maybe you should think about what I'm saying here because I have a point. Then the other thing I was going to say that I think the other way to think about it is where it's challenged me as a person is maybe you've noticed this with your parents, but like you talk about something from your childhood and they take that as like a criticism of them as a person and they're like, that didn't happen or that's not true or you're so sensitive, right? They're trying to argue with you about your feelings and there's nothing more infuriating than someone trying to argue away the existence of something you feel.

38:40And so that's something I try to think about with my kids is like, if they say something or they say they don't like something that I did, I can't be so sensitive that like, I have to deny the truth of that rather than going, your feelings are your feelings. I know who I am. I know what I was intending. I didn't mean to hurt you. So I'm not like racked with guilt, but I do want to make you feel better. And I do want to not make you feel that way in the future. Well, and I think that's a huge piece of maturity for me as I get older is that we all are allowed to our own feelings about the situation.

39:18and the separation of that is an emotional boundary of you get to feel this way and I get to feel this way and not take on each other's feelings of what this experience was for us. Yes, and you're just never gonna win arguing with that person about how they don't actually feel that way or it's not fair for them to feel that way or it's hurting you that they feel that way and just be like, oh, okay, you feel this way. I didn't mean for you to feel this way. So let's like talk about that. that, right? And yeah, I think we're talking about boundaries, talking about awareness, talking about empathy.

39:52These are all things that are hard under normal circumstances. I think they're really hard if you didn't have that modeled for you or you had the opposite of that. And so when you think about why people get so mad on social media, well, that's most people. Right, right. I actually was just talking about this in an episode recently that when we understand what emotional boundaries are and we try and put them in place in our life, there's a very strong chance you're trying to put up an emotional boundary with someone who does not have any experience in it. Yes. Right? Your mother-in-law, your dad, your partner.

40:27If they knew about that, you wouldn't be in this situation. The boundary would go unset. Right. So it's already a ton on your shoulders to try and establish the emotional boundary and hold it strong, especially in the face of a person who is super unfamiliar with what that is. It's going to feel like an attack. It's going to push every button that they have, which is why this boundary doesn't exist already. Yeah, and it's really hard. I'm going through some version of that myself where it's like you put up the boundary and you hope the person's like, oh, that's what it takes for me to stay in your life.

41:00Got it. We'll respect it. But that's not usually what happens. And usually they go, well, then fuck you. I'm out. And you have to sit with that. And then there's a part of you that goes, no, no, no, no, no, no. And then you're back to violating the own boundary. And so I think just understanding that when you draw a boundary, there is a good chance that the person is going to go in the other direction. And that's going to be sad, but that's also kind of what you want or you wouldn't have thought the boundary was necessary in the first place. Yeah, 100%. How did you come to the wisdom that we know you for today?

41:44Like, did you grow up with this information or you found it? Certainly not. I think the reason I found it, and it struck me so much, when I read meditations at like 19 years old in my college apartment, sitting at a table like this, it was like, holy shit, where is this? You know, like, this wasn't what they talked about in church. This wasn't what my parents talked about. This isn't what my friend's parents talked about. This isn't what they talked about in school. It was like, oh, there's people who have thought really hard about being good at life and being a good person in life that doesn't have, you know, those notions of sin attached or hell attached or because I fucking said so attached or, you know, like you're such a disappointment to us.

42:33Like there was none of that. It was just like, hey, this is the journey that people have been on for a long time. And I think it just struck me because it was so different than what I had, not only than what I had gotten, but it was what I was looking for. And so I wouldn't say I have that wisdom. I would say I'm good at explaining and talking about and connecting that wisdom to other things. That's what I feel like I do. I feel like the conversation that I'm having about stoicism in my work is not from on high looking down, but looking up with the audience. Yeah. Did that launch you into this world of reading all of the Stoics?

43:24Yeah. Because I've heard you talk about it before, and you're so passionate. Obviously, I've read the books. But it was a long time from 19 until this became what you were known for. Yeah. I mean, I liked all this stuff. And I think I was primarily, though, in my early 20s, interested in it as a philosophy of productivity or success. In the same way, there's something attractive about the prosperity gospel because it's like, if you do this, you will get this. But you're not actually understanding what this is and why it's important. And so I think my relationship with it grew and evolved and I added to it my own experiences and then other schools of philosophy that I studied.

44:13So it took a while. And I remember actually I got – someone offered me a chance to write what was The Obstacle is the Way in maybe like 2008, 2009. So like several years before it came out. And my mentor, Robert Green, was like, definitely don't do it. Just a tiny name drop. No big deal. Well, yes. I mean, it was sort of my dream person to work for. But I was like, hey, it's here. The thing that I've always wanted is here, my shot. And he was like, this is not your shot. You are not ready. And that was the hardest thing in the world to hear. But he was totally right. I needed to go make a bunch of mistakes, do a bunch of things, see a bunch of things.

44:58until I could really write and talk about it. And then even then, you know, my understanding of the words, even in my own books, is different many years later. I, that book, I told you this when I first emailed you, was hugely impactful for me. Oh, that's so cool. And I didn't intend to read it. It was, I had read your marketing book and then I know it sounds so ridiculous what I'm about to say, but I was sort of like, Stoicism. You know, I'm very emotional. I've not, it feels like the opposite of who I am. It feels like this will not be helpful in any way. And my boyfriend is basically like dating Yoda.

45:39He's very calm. He's very centered. And I saw it on his bookshelf and I didn't have a book. So I was like, I'll try it. And then I devoured it. It was so helpful for me. Because it came at a time in my life where I really was grappling with so many things that had happened to me. And I was like, why does this stuff happen? And the idea that if you can get past that obstacle, it really is the skills or the tools or the resources that you harness in order to get past the obstacle is how you become the next version of yourself. Yeah. And I actually understand the book like differently. there's this thing from the Stokes that you never step in the same river twice, that everything is different because you bring something different to it.

46:27So I think when I was writing the book, I was very much thinking about it as like, I don't know, like an analogy would be like, you're a small company and you don't have all these advantages compared to your big competitor, but that makes you creative and therefore you're better than your sort of bureaucratic larger competitor. So I was thinking about it in terms of like how constraints make us creative or create opportunities. And that's definitely one read on the idea that the impediment to action advances action. What stands in the way becomes the way, which is what Mark Surreal is talking about the book is based on.

47:02But as I've gone through stuff and seen more things, I've also come to realize that it's less glib than that. Like it's, he's saying that what happens to you happens to you. And that's an opportunity for you to be a different kind of person as opposed to like one door is closed. So you go through this window. Do you know what I mean? Yeah. Like that, that he says basically that every obstacle or impediment is an opportunity to practice a virtue. And that virtue might be acceptance. It might be forgiveness. You know, so like when you hear the obstacles away, and obviously I was writing towards like, hey, this is how you scrappy startup becomes more successful.

47:53But I've come to see it more now like somebody betrayed you, somebody stole from you, somebody hurt you when you were little. Now you're wrestling with that. What is that an opportunity for you to be as a person that is some form of greatness? Right. And so I, yeah, my, my relationship to it has changed because you just realize that some things like the loss of someone you love or a pandemic or something that happens in the world, it's not like, Oh, where's the silver lining, you know, or like, Oh, but now I can do this. It's more like, what is this situation demanding of me and how can I step up and be that?

48:37And I think that's a more meaningful way to think about it. Yeah. I am wired to look for the silver lining that I'm just always like, okay, well, how can this be for me and how can I learn? And my partner is very much accepting, just like it is. It just is. And sometimes it just is. And he had been talking about that for as long as we had been dating. And I was just sort of like, well, we're going to agree to disagree. And reading that book was really helpful. I wouldn't say that I'm all the way there, but I'm so much more accepting of especially people, of people that in the past, I would think, well, this is toxic energy or this is, you know, this person, I'm talking about family members, like this person's crazy or that I'm just sort of like, it is what it is.

49:28And when When I try and fight back against that, I only make my life more uncomfortable. Like it's that Byron Katie quote, defense is the first act of war. That when I try and like defend what I think should be true, because like I'm not upset that you're acting this way. I'm upset because I think you shouldn't be acting this way. So if I can just sort of accept that that is what it is and then go about my existence with or without you in my life based on how you are behaving, that has been huge for me.

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52:58lie. Yeah, I think we saw this during COVID for sure, where a lot of people's arguments over this or that or this or that boiled down to, but I wish this wasn't true. Right? And I see that even in relationships with my spouse. You're mad at this person, but really what you're just saying over and over again is like, I wish the facts were otherwise. Yes. Like, I wish you had not done this. But they did do it. It did happen. This is the situation that you're in. It's raining. Like, yeah, it's not supposed to rain. And yeah, you wanted someone to bring an umbrella and you told them to make back. All that stuff is true.

53:40But now this is what it is. And so you can torture yourself and them going in this loop over and over and over again, hoping that if you say it enough times, you can will different facts into existence or you can accept those facts and go, okay, what can I do with this hand that I have? And so I think acceptance has kind of a really nasty connotation. Like there's a passivity in it and a weakness. Oh, I think it requires so much strength. And not only does it demand an incredible amount of strength and fortitude, but it's also the first step in doing anything about it. Like you can't change something that you deny is not the way that you want it to be.

54:35Accepting reality on reality's terms is the first step. This is, I think, politically a huge mistake that people make, right? They don't want something to be true about human nature, about other people, about the world, about public opinion. So they just think if we just say things enough times, you know, we can change the fact that a good percentage of the population or we can wish away the fact that a good percentage of population does not agree with us on this. versus, hey, this is morally correct, our position, but for whatever reason, and actually we need to understand what that reason is, a large percentage of the population does not agree.

55:15The law does not agree. And so how do we change that, right? So the acceptance, like in addiction or recovery, acceptance is the first step in admission and acceptance, is the first step in trying to chart any kind of new or better future. And your denial is not only not true, but it's harming the thing that you purport to believe in. How do you feel like for people who are listening or watching this, if they're trying to figure out if they're in denial in a certain area, are there things that you would identify as like, this is probably a pretty good sign that you're not being honest with yourself about what's really going on.

56:05I've been saying lately in some of my talks, the thought it's different this time is the first sign things are about to go super sideways. It's different this time. It doesn't apply to me. I'm the exception. I don't know. If only I could get them to see, whatever. When you have, I think it's hard because if fundamentally any creative person or entrepreneurial person or person in a position of leadership is inherently in denial, is inherently irrational. There's a great quote that is basically like, a rational person accepts the world as it is. An irrational person seeks to change the world. So it's like fundamentally change and progress depends on the irrational man.

56:58And so it's hard. Like you have to have that. Like you have to believe that what you're doing can make a difference. You have to believe that you have agency. You have to believe things can change. You have to believe that you matter, that you have power. You have to believe all that stuff. You have to believe that you're right even though all the people that are telling you the odds are against you are overwhelming. You have to believe that they're wrong. So you have at the core of who you are is some bit of irrational rejection of status quo or the odds or whatever. And you need that, but you can't have that in everything that you do.

57:38Well, I would also, I wonder too, if there's something to like, you keep trying to do the same thing and you're never getting the results that you're looking for. Sort of like doing the same thing over and over and expecting. The definition of insanity. Right. Um, but I encounter this a lot in the women in my community. They'll say, you'll start to talk about something. They're like, oh, I know. Yeah. I know. I've read all the books. I know. I know all that. And I'm like, no, you don't know. Because if you actually knew, then you would understand how to apply it in a way that would get you to the result you're looking for.

58:09So it's, you know, knowledge isn't power. Applied knowledge is power. So you don't know. and there's some piece or maybe many pieces in the equation that if you just tweaked them a little bit, you'd start to really move. Well, everyone knows, right? Everyone knows how you're supposed to lose weight and how you build a business. The facts are, the thing is pretty simple. Yeah. There's just some part of it, a part of us that doesn't believe it, that doesn't believe we could do it, that doesn't believe that we have what it takes. There's some part of you that has not fully accepted that. or has not fully committed to that.

58:49And I think that's going to make it very hard to do whatever the thing is that you want. So it doesn't matter that you know. And I think one of the things you learn in therapy is there's a big difference between intellectually understanding something and emotionally understanding that thing. And I think it's really common and really easy to intellectualize or to be, yeah, yeah, yeah, I get it. Okay, it's clear. but you're like 40 % of the way there. This is probably why, and I'm not a fan of them and don't do them, but I think this is why psychedelics are so powerful for some people is that thing that they knew or that they kind of understood, it resonates with them in some way.

59:31The defenses are down and they get it. Because whenever I talk to someone who's like, oh, I just did ayahuasca or whatever, I'm like, what did you learn? I learned that I was going to die. Or it's like, I saw a little version of myself as a kid and I was scared and I realized I've been. It's like, yeah, this is like 101 of life, therapy, philosophy, religion. And you realize, like, I'm not making light of it. It's just like knowing it and knowing it are different things. So real. Have you done psychedelics at all? And you never will? No. And I really hate that people call it doing the work. Well, I will say I'm so fascinated by this.

1:00:14And I have a couple people coming on as guests soon that are very into psychedelics. I'm really curious about exploring the idea of spiritual bypassing. Yeah. That you get so into doing the work. I also, I have done psychedelics, so I'm like not, I'm not dogging it. I am the queen of like, let me try a thing and see what I learned. but that people do it so much that they're sort of at least from the outside it seems like they're getting to this place of enlightenment but I'm confused about what the enlightenment is for because I thought the whole idea was that you were taking what you learned and applying it to your very real life but if all you do is keep escaping through whether it's you know I have friends who like meditate for five hours I'm like it must be nice to be rich and not have kids because what are you talking about?

1:01:07Like, this is not how normal people behave. And you have a choice as a human being to just live your life on another plane. But I thought that the point of the enlightenment was so that you could bring it back down to this very real life that you're living inside of and use it to help yourself or help others. Yeah, it's like, you know, you sound like a drug addict. You're like, I did this thing, it felt magical. And that's why I like to do it a lot. I keep going back, yeah, 100%. And then you found a way to tell yourself that it's like medicine. Yes. So anyways, I tend to be skeptical or somewhat cynical about anything that presents itself as like a magical solution to problems that human beings have been struggling with for basically all of the human experience.

1:01:53Yeah, there is a lot of, I have friends who are in the military and have done journeys that are guided that have been so healing to them. So I just, I want to at least - It's very different. I actually make that exception too. Like if you have like treatment resistant depression, they're already giving you a lot of different medications. And so like try them all and see what works. And also I suspect if that's you, you're not the kind of person that's like now wearing weird hats and like going on these retreats. Going to Burning Man. Exactly. You're trying to get some relief from something that's making it impossible for you to function as a person in the world.

1:02:36To me, that's very different than, you know, this sort of, I don't know, whatever the sort of like commercialized sort of like medical tourism that it feels like some people have decided to get into. Do you ever push yourself to do things like this that your instinct is like, absolutely not? This is not for me. Well, a much less controversial version of them is probably the reaction you were having to my book, which is like anytime I see something that's like a book that's just like selling like crazy, I'm like, well, I'm definitely not reading that. And then I read it and I'm like, oh, this is why it's so huge.

1:03:18It's so funny. It's actually good. It's really good. It deserved all of it. Like very rarely have I picked one of those up and I've been like, this was totally unwarranted. I'm like, no, there's a reason Malcolm Gladwell is so huge. I love Malcolm Gladwell. Of course. Yeah. But you're just like, oh, this is why. There's a reason. You're just being like a judgmental asshole is what you're saying. Yeah. Well, I think probably too as an author, you're like, hmm. Well, the question of like, how did they get that? Yeah. Well, and then you start comparing and you're like, well, dang it. You know, so it's my own thing.

1:03:51And I feel like it's probably better to not soak it in. And I definitely have had times where I've read stuff and I'm like, oh, I get why this resonates. But I don't. This is not my jam at all. That is a huge breakthrough that I try to even tell people who like tell me that they don't like me. I'm like, yeah, like I'm not for everyone. Yeah. And just like having having the under like when you have understanding that what you do is not for everyone, that it was literally not designed for every kind of person, but designed for a specific kind of person, that should be transferable to all things and realizing like this person is making things for people that are not me.

1:04:33And if they like it and it's getting, it's doing something for them, that's awesome. Why would I have a problem with that? Yes. It's so wild because I think this happens a ton in personal development that people get so fired up and they'll just like hate a specific style of teaching. And there's lots of people that are not for me. But if that person and their style is helping someone, then why do you care? Yeah, I think, look, there's definitely some people who are fundamentally dishonest or unethical or exploitative. Sure. And like I'll draw a line there. But like comedy is a good example. There's so many different types of comedians.

1:05:11For so many different, like there's styles of comedians. There's generations of comedians. There's comedians for certain groups, certain experiences, certain age demographics. And there is this instinct when you don't like a comedian to say, like, they're not funny. And no, it's that what they're talking about is not funny to you. To you. But if there is a stadium of people laughing at that person, chances are they're right and you're wrong, right? And I think if you want to talk about accepting, to get to a place where you're like, that person is funny but not to me. Or that comedy is for a phase in life or a type of experience that is not me.

1:05:55And I have no problem with that. I'm okay with that existing. But there is this instinct. What's the expression? Don't yuck, someone's yum. That's good. But there is this thing. It's like when somebody says, like, I like this, and your instinct is to be like, let me tell you why you're wrong. Which goes back to what we were just talking about, which is like somebody else's feelings or somebody else's feelings. And they're in no way mutually exclusive with your feelings or your tastes. And to be able to just be like, cool. Yeah, Amy Poehler has this quote in her book where she's talking about other moms and how they mother.

1:06:31And her line that she uses over and over is, good for her, not for me. Yes. Just like, good for her. Not for me. Good for her. She's going to make an organic lunch and one of those special, you know, things and like the kit for her preschooler and they speak three languages and like, good for her, not for me. Yeah. But we're so judgmental about how other people do things. A great example of this, and you don't consume social, it sounds like, but I happened to notice or the algorithm wanted me to notice a ton of Reels that were women in their late 30s and 40s who were, you know how you can take a video and like add your own video on top of it?

1:07:08I don't know what it's called. Yeah, it's a reaction. Yeah, there you go. So they were doing that with young women, women who are 19, 22. And those younger girls would be talking about a style or a lot of times it was like a scrunchie or a puka shell necklace, stuff that we had when we were younger. And these women in their 40s are just eviscerating these young women. Like, we already did that. We already did it. And they're so mean and so vicious. I'm like, what is wrong? Are you okay? Yeah, yeah, sure. Are you okay? They're definitely not. This is wild. Like, this girl is not hurting anybody.

1:07:45She's literally excited about a new headband that she got. All she's doing is putting her joy into the world. I got a new headband. It's so cute. And you are using that as your content to rip her apart. And you're 20 years older than she is. Yeah. This is embarrassing. Yeah. Just let them do what they're going to do. You don't have to get it. And do your own thing. Well, and I think what, to go where we were talking about earlier, is part of that is like they are hearing something very different than that young person is saying. Right? Yeah, that's real. And so like when you're – if you're fundamentally insecure or fundamentally don't like who you were at that age, somebody like – like I forget who it was, but I saw some woman and she was like – some overweight woman and she's talking about being like bullied on the internet.

1:08:35And she was like, why is it a problem for you that I don't hate myself? And I think a lot of the backlash about the body positivity movement is fundamentally about that. So it's like, I paid off my student loans. Like, why should you get debt relief? There's this part that goes like, I feel disgusting and I hate myself and I'm in pretty good shape. And here you are, like medically obese and not healthy and you don't hate yourself. That's not fair. And so I think a lot of it is that. Like I suspect all moms feel guilty. I was talking to my wife about this in here the other day. I think moms are much harder on themselves than dads are.

1:09:22A billion percent. And so if you walk around feeling like you're not doing enough, you're not good enough, that you're falling short in all these ways, And then you see a woman who is confident or focused on things other than the things you're focused on, that can feel very much like an indictment of you. And I wonder how much of the anger towards you is like it would that anger would never exist if you were a male author. Oh, all day long. Oh, this is like I have internal debates with myself all the time is expressing any kind of success. for as long as I've been in business, I always thought, well, gosh, I never had an example.

1:10:07And I wondered this, right? I would look at Oprah. I would look at Sarah Blakely. I would look at all these women in business that I know are billionaires and they never talked about it. And I was like, what is going on? How are women supposed to be inspired? And to look at other people who have figured it out, like it seems from the outside, like Sarah's killing it as a mom. She's built this amazing bit. Like, why is she never talking about that? Why is she pretending that she's a regular person? Right. Like, you have, yes, there's a whole other thing. But then, so I was like, well, I'll be the one.

1:10:42I'll say, like, this was years ago when I would be like, oh, we sold out this conference. Like, 8 ,000 women are coming and we're doing this thing. and it was, I mean, I may as well have painted the target on myself, never thinking because I grew up without any money, you know, like so many people working three jobs, doing the thing that I thought, well, if I talk about it and if I tell you the path that I took, you don't have to follow my path, but maybe it inspires you to do something in your own life. And what I actually got, it's like what you said earlier, that it was like, we're going to make this so painful for you that you will stop talking about these things.

1:11:22And I have only recently become conscious of how many things I deeply care about that I have stopped talking about as a podcast host and as a writer, because I know that people are upset if you talk about money or they're upset if you talk about health. They're upset if you talk about body image, like any of these things that I know are going to have a visceral response from the audience. So then I don't speak about them at all. And we're getting to a place in our culture where we're just, we're talking about nothing because it's like, you're not, you're no longer playing to win. You're playing not to lose.

1:11:56I think the problem is it's actually worse than that. So you have sort of people who are sensitive to being yelled at, to being criticized, to being made to feel shame or whatever. And then you have people who are apparently immune to those things. And then, no, you don't. You don't. Because what I'm saying is like, so it's like, look, if you treat everything with antibiotics, you eventually create like superbugs that are resistant to antibiotics, right? So if you try to shame people for every sort of lapse in language or poor piece of judgment, if you try to say, oh, that post was insensitive or misguided, you're canceled, you're gone forever.

1:12:36What that leaves you with is either the people who take no risks, stand for nothing, are meticulously calculating everything they do. So that never happens to them. And then the people who are like, I don't give a fuck, right? Like I have zero shame. And those people are the worst. And, and so you, and they'll talk with anyone, engage with anyone, say anything as long as it's provocative or, you know what I mean? Yeah, it's clicks. Yeah, so it creates the opposite of a world that you think you want because you think you're holding people accountable, but really you're just selecting out. You're getting rid of all of the – by nature of the fact that this person is trying to apologize, by nature of the fact that this person feels bad about what happened, you're actually like eliminating them from contributing to popular culture and you're leaving only the people who are incapable of feeling any of those things.

1:13:32Incapable of feeling or perfect at playing the game. Yes. And then it's just like, it's just a picture and an emoji and it means nothing. And so on some level, I am the prime candidate, the way I was raised and everything. I am the prime candidate for using shame as a maneuver to get me to stop moving. I don't mind failing. It's like I wouldn't be where I am if I didn't fail continuously. uh it's the it there it's very easy to say specific things and have everything crumble because i'm like oh my god i you know what's that brene brown like um uh guilt is i did something bad shame is i am bad sure and so i am like you will it's so easy to um to use that and have me stop moving.

1:14:26And when that's happened in big ways, which it obviously has, it took a lot of therapy and a lot of prayer and a lot of meditation, a lot of these things that I thought I had already, like I had this stuff in droves, but it took everything in me to then learn and grow and get past that. And what finally made it so that I could feel like I'm doing my work the way I've always done it to get back to this place was that my core value is believing that the only way you and I are going to get better or Jack or your team, any of us, is that we have to try stuff and we get it wrong and we have to learn from it.

1:15:08That is a core value of mine. If I want to grow, I'm inevitably going to do something where I have to learn from it. And if I believe that's true for every human, then I have to also give myself that grace.

1:15:24Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and it would really help the show. We appreciate it. I'll see you next episode.

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