The Jordan Harbinger Show - 753: A Clandestine Crossdresser's Conundrum | Feedback Friday

Episode Date: November 18, 2022

When you're a secret crossdresser who's had a secret affair with another married man whose untimely death left you grieving in secret, it's got you wondering if you should bury your secret things before you die and your wife discovers what you've been hiding from her for all these years? We'll try to find an answer to this and more here on Feedback Friday! And in case you didn't already know it, Jordan Harbinger (@JordanHarbinger) and Gabriel Mizrahi (@GabeMizrahi) banter and take your comments and questions for Feedback Friday right here every week! If you want us to answer your question, register your feedback, or tell your story on one of our upcoming weekly Feedback Friday episodes, drop us a line at [e-mail]. Now let's dive in! Full show notes and resources can be found here: jordanharbinger.com/753 On This Week's Feedback Friday, We Discuss: Good news! Skeptical Sundays with David C. Smalley will be back in 2023! Should you bury evidence of your crossdressing life and an affair you had with a man before your wife discovers it upon your death? Your parents want to give you and your siblings an inheritance, but how do they compassionately explain excluding your brother who's living as a monk and would have to donate his share to the Church? You envy your siblings whose lives have worked out better than yours to the point where you don't feel empathy for them when they endure terrible things — like having their houses washed out to sea in a hurricane. How can you cultivate a better attitude toward them? You've been appointed as class prefect in your high school, but your less ambitious classmates have chosen to bully you instead of following your efforts at leadership. What can you do when your peers don't respect your authority and the administration refuses to help? Should you remain as a partner at the large law firm where you've been for the past six years when your higher-ups treat you like a doormat, or should you pursue getting a fresh start somewhere new? Have any questions, comments, or stories you'd like to share with us? Drop us a line at [e-mail]! Connect with Jordan on Twitter at @JordanHarbinger and Instagram at @jordanharbinger. Connect with Gabriel on Twitter at @GabeMizrahi. Sign up for Six-Minute Networking — our free networking and relationship development mini course — at jordanharbinger.com/course! Miss our two-parter with professional pickpocket See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Welcome to Feedback Friday. I'm your host, Jordan Harbinger. As always, I'm here with Feedback Friday, producer, the cough syrup to my hard candy in the syserp of life advice, Gabriel Mizrahi. On the Jordan Harbinger show, we decode the stories, secrets and skills of the world's most fascinating people and turn their wisdom into practical advice that you can use to impact your own life and those around you. We want to help you see the matrix when it comes to how these amazing people think and behave. And our mission is to help you become a better informed, more critical thinker so you can get a much deeper, understanding of how the world works and make sense of what's really happening, even inside your own mind. If you're new to the show, on Fridays, we give advice to you, we answer listener questions. The rest of the week, we have long-form interviews and conversations with a variety of really amazing folks, from spies to CEOs, athletes, authors, thinkers, and performers. This week, we had General Robert Spalding on how China is, the Chinese Communist Party in any case, is low-key at war with the United States slash the West. No crazy hype here, just an outline of the very public game plan on stealing technology and capturing international institutions to fight Western

values. We also had Angela Duckworth from the vault on grit and resilience. This one is, we did this one of why is back, but it was one of the most popular episodes at the time. It's an irresistible subject matter that you can put into practice right away. So make sure you've had to listen to everything that we created for you here this week. Quick announcement before we dive in, Skeptical Sunday is coming back next year. Not sure exactly what time or date, but David C. Smalley have recorded a bunch of them. They should be out on a fairly regular basis. So if you're a fan of Skeptical Sunday and or one of the gazillion people who have asked me when those are coming back, the answer is 2023. And I know I'm also really excited about that as well. These are super fun to

record. I'm going to try and fit them into the schedule where they belong. And I think they're just going to be even better than the ones we've already aired. All right, we've got some fun questions. We've got some dozies. Let's do it. Gabe, what's the first thing out of the mailbag? Dear Jordan and Gabe, I'm 75 years old and I've been cross-dressing for over 60 years, accumulating a wardrobe of very sexy lingerie, dresses, and cosmetics. My wife forbids my cross-dressing, so all of my feminine attire is well hidden. She's caught me a few times, and each time I promise to never wear these clothes again. I then regretfully purge my things, only to slowly succumb to my desires and rebuild my wardrobe,

bra by bra. After 47 years of faithful marriage, I had a one-year affair with a married guy my age, the only other person who has seen me dressed in a dress, bra, and nighty, pink with blue lace, if you want to know. You know, I was just about to ask. I did want to know. Thank you. Continue.

We need the details. I need the visual. The experience with him was thrilling for both of us. The affair stopped when I was diagnosed with prostate cancer, and shortly afterward, he died from COVID. I couldn't acknowledge his death to anyone, but grieved and got through my loss. On top of that, when our oldest son was around 10, he walked in on me and saw that I was dressed in a pink bra and panties. I quickly hid, and neither of us ever mentioned the incident again. Several years ago, he died from an overdose, and we discovered his own stash of lingerie,

and that he had been photographing himself cross-dressing. A couple weeks before he died, my wife and I could tell that he was high on drugs, since we're Baby boomers were ambivalent about drug use, and we just let it go. His death, which was quite graphic and shocking, severely traumatized my wife, and she refuses to talk about it. We were unrelenting in blaming ourselves for his death. We didn't blame each other. We may have felt it, but we never said it.

We also had a disastrous encounter with therapy for one of our other sons that permanently drove her away from ever seeking help. Otherwise, we're pretty happy with our life as it is. is. I'm now at an age where I might die suddenly, and my stash of lingerie and an encrypted flash drive of love letters and photos would be discovered by my wife or son. I'm not sure whether to leave some kind of note with my clothes or preemptively get rid of them and never replace them, which is unlikely due to my compulsion. I really love cross-dressing and don't want to give it up, but I also don't want my wife to have a mental breakdown due to my betrayal. Another option is to get rid of

everything and then secretly wear her things, but they're so boring and plain, and she'd probably realize if her things were being worn. The idea of coming out is a total non-starter. Should I bury my secret things before they bury me? By the way, I'm all dolled up as I write this, signed, loving this wardrobe, but hating the closet. Holy smokes. What a story. Wow. Okay, first of all, heartbreaking in so many ways. Let's acknowledge that, but also, this guy is funny. He is. Also, I think this is a first for feedback Friday. I'm happy to finally have some cross-dressing septuagenarians in the mix here. Yeah, that's a first. Yeah, you know what this sort of reminds me of, Gabriel? It places the lotion in the basket. Now, I know that that's not entirely

fair, but that is what pops into my head. It's fair enough, yeah. It's really unfortunate. That's more of a Jordan problem than a cross-dressing problem, though. I want people to know, I am not shaming you. Actually, it's me who should be ashamed that that's the only thing that pops into my head when I'm thinking about somebody who's doing that. Perfectly harmless hobby most of the time, I suppose. But in all seriousness, I find this letter fascinating, Gabe. This guy shares all this incredibly painful and complicated stuff, cross-dressing, having his son catch him, cross-dressing as a child, being in the closet, having an affair with another guy at 70-something years old, losing that guy, going through cancer, then losing his son to an overdose, and then something, something, another intense drama with my other son.

But then his question is, should I donate my Victoria's Secret Collection to Goodwill before I die so I don't get caught? Like, what? What? He took a huge detour through six massive topics. I just don't even know what to talk about here. Well, maybe we should just start with that, that this guy has clearly been through a lot in his life,

maybe even more than he fully appreciates. And he seemed to really want us to know that. Right. So obviously, this is a guy with a huge secret, the cross-dressing. But it's not the only secret in his life. Right. There's his orientation. there's the affair, there's the loss of the guy he was seeing, which he just grieved in private.

When he and his wife noticed their son was on drugs, they just let it go because they were ambivalent about drug use, in their words. I'm sure that is an incredibly painful thing to live with, but I wonder if they were avoiding a difficult conversation there and they just let it go thinking like, uh, we're old hippies, you know, is that true? Is that the case? Could be. They felt guilty about his death and then they blame themselves and each other, but they never said any of that to anyone or each other. And his wife refuses to go to therapy. And the idea of him coming out to use his words is a total non-starter.

I mean, this is just secrets on secrets, man. Yeah, yeah. I see where you're going with this. So this is a guy who might prefer living with those secrets. It does seem that way. Or at least this is a guy who's comfortable with things being left unsaid, which kind of lets him off the hook for having to acknowledge a ton of unpleasant stuff and then just work it out, especially with his wife.

Totally. There's a lot going on in this marriage that is not being addressed. The cross-dressing is the most obvious, but that seems honestly like the tip of the iceberg. Yeah, but you know, Gabe, other than the multiple traumas and earth-shattering secrets they've been sitting on, they're pretty happy with their life as it is. I mean, are you, how can that be the case? They say that they wrap their letter with like, ah, but we're pretty happy. I'm thinking, really?

But we're pretty happy. We're good. Yeah. That was an interesting comment. Well, look, maybe they are. Right, sure. I don't want to take that away from him, but that does seem just, I don't know, a little simplistic.

Yeah, I'm not trying to say you shouldn't be happy, but maybe this guy just is really resilient and optimistic. That's possible, too. But the overarching theme here, to your point, is secrecy. You know, whether to throw away his clothes, we can get to that, but that is far down my list of shit we need to talk about here. Totally agree. Yeah, I'm just, I'm not exactly sure how to help.

What I want to say is, you're a locked box. you don't have to be. Look what that's doing to your life. It must be exhausting. But he seems pretty committed to being a locked box. Yeah, he must be because that would be a huge step for him. He's hidden away parts of himself. It sounds like to protect his wife. You know, he's afraid of giving her a mental breakdown. I'm getting the sense that she is pretty fragile. I don't know if in general or just these days, but that means that he can't fully be who he is. And yeah, that is exhausting. Right, but I'm wondering, is that a deal he can accept? He would probably say yes, but this whole, you know, the whole coming out as a non-starter

comment, I'm a little confused by that because, well, we don't know if he meant coming out of the closet potentially as a gay man or as a byman, or if he meant coming out of the closet as a cross-dresser, maybe he means all of it. But in a way, he already is out of the closet. I mean, he might not be out to the world, but his wife caught him a few times. She knows his secret. it. She's just pretending it doesn't exist or she's hoping he's going to get over it, which, let's be honest, that ain't going to happen. That's what makes me sad, right? This double life that he's

living. He's stuck in the cycle of dressing up, getting caught, throwing away the clothes that he loves in the makeup, missing them, buying new ones, keeping the secret again. And I think that speaks to the fact that this is just a part of who he is. I agree. He can't hide it. He can't hide it. Well, right. Okay, but then there's this other thing about his son, the one who died, he walked in on his dad dressed up and then later he starts cross-dressing. We have to talk about that, right? Yeah, we have to. I don't know what to make of that. I think Freud would have a field day with this, as would maybe any other psychologist. It just does make you wonder if an interest like this is contagious somehow. That's not really the right word. I don't mean to pathologize

cross-dressing. I know it's not always a fetish or dysfunctional thing. It can be an identity thing or it can be both. It might even be that for him, but something different in his son, like a shame thing, because he probably caught him and was like, never say anything. And the kid was like, now I'm so curious about this thing that I'm not supposed to deal with. So it might have been a thing that dad was into for other reasons. And then the kid got into it for these different reasons. I don't know. I really don't see anything wrong if this guy wants to dress up like Nikki Minaj when his wife is at the supermarket or whatever. But he must have implanted the idea in his son's mind somehow, right? Must have. He must have. Otherwise, that would be a hell of a coincidence.

Exactly. Yeah, I don't think that happened. Right. I just don't know how that fits with the rest of his story or if it's just a random detail. Well, I wonder if he told us about that because he thinks there's some connection between that and his drug use. If maybe that's part of what is so complicated about the cross-dressing. Maybe, but I'm pretty sure his son didn't start using because he saw his dad dulled up one day as a kid. A severe drug addiction, that has much more complex. causes. There's got to be more to that. Yeah, I agree with that. Look, I hesitate to say this because I really don't mean to make the guy writing and feel worse. He's been through so much here. I know this

is really hard to live with. But my hunch is that growing up in a family with this many secrets, you know, a family where maybe you don't acknowledge when there's a problem, or you don't ask for help when you're in trouble, or you just kind of absorb the message that you're supposed to shoulder your problems alone, I would think that that has more to do with diverse. developing an addiction than, you know, seeing your dad in a teddy one time, as shocking as that might have been. Man, that's a good point. But look, probably a lot of different things contributed to his son's addiction.

And we're not trying to pin blame on anybody. There could have been a genetic component. Right. He could have had his own mental health problems. He could have taken a prescription and gotten hooked. Who knows? I don't want to be like, it's all you and your wife's fault with your secrets, right? Because his son was responsible for his life, too.

And there's an element of just bad luck, you know, getting hooked on back pain pills. or something, like, we just don't know. Totally. Not my intention to pin it all on him, but that's got to have played a role that you can't really talk about certain things, yeah. I do think you're on to something. How avoidance can take a toll on everyone in a family. And maybe that's why he included that detail in his letter, because, again, he knows on some level that a lot has gone unsaid.

So, look, I don't want to sound like a broken record, but this is complicated stuff. You're dealing with a lot of huge questions and experiences, and this is exactly the kind of work you can really only do over a decent period of time in therapy. You have had 75 years of truly intense stuff to work through. I want so badly for you to unburden yourself. I don't know if that's going to happen, but that is the best advice that I can offer because there's decades of stuff that goes into each one of these. We are not going to solve this problem. In 10, 12 minutes. Yeah, I agree. Totally. Yeah. The loss of your son, the affair, your orientation, your dynamic with your wife. Of course, the cross-dressing. Those would be high on my list of things to talk about.

But, I mean, dude, look, you're dolled up as you wrote us this letter. Your only other solution is to wear your wife's things while she's out, except you guys have totally different styles. I got a good hearty laugh at that, by the way. Just a funny comment for one. But also, I kind of get it. Hey, if you're going to get dolled up, you want to go all out. You don't want a half-asset. You don't want the basics. I mean, I get it. He's fashion nova, and she's Anne Taylor. It's just not his aesthetic. So is she Anne Taylor or is she Anne Taylor Loft? I think Ann Taylor loft is like the cooler, younger Ann Taylor. Okay, I knew there was something like that.

Okay, so she's probably Ann Taylor. That's the problem we're dealing with. Anne Taylor, yeah. I don't know why I know that. Well, maybe you got a little extracurricular activity you want to tell us about, Gabe. Yeah, uh, pink with the blue lace if you want to know. Fair enough. You do you, bras.

Waydos bras, bra. So, look, in a way, you might be asking the wrong question. I don't know if the question is, should I bury my secret things before they bury me? I think the better question might be, why is this secret going to bury me? And should I be working so hard to keep it a secret at all? Yeah, well put. And his answer to that would probably be, no way I'm coming out, no way I'm putting my wife through that. I'm 75.

I don't have a ton of time left. So I'm just going to carry the secret to my grave. And you know what? That's his choice. It absolutely is his choice. But then he needs to accept the price that he's going to pay. and has been paying for living this way, which sounds like tremendous shame, sadness, loneliness.

Stress, man. Stress, yeah. I am terrible with stuff like this. On top of the grief and the emotional distance he feels, I would feel so just knotted up with anxiety all the time. Are they going to find it? Are they, is my wife going to look at my stash? Is my other son going to find my flash drive?

Yeah, it's a lot to deal with. And I just don't know if those experiences are worse than deciding, You know what? I am 75. I've been through a lot of my life. So this is who I am now. Sorry. Right. I guess it ultimately comes down to which pain he wants to live with. Right. So I would very much encourage you to dig into all of this. Your wife might not want to talk to anyone again and, hey, that's fine, but you can. And I do think that's extremely important after everything you've been through. So thank you so much for sharing so much of yourself with us and your collection over there.

I hope you get to delve into all of these experiences more. We're wishing you the best. And, hey, if you decide to keep building your wardrobe, check out our sponsor, Adorme. The new face of lingerie, superb quality, great fit. We actually have a code that can give you up to 50% off your first purchase. We'll drop that in the show notes for you. Just do not tell your wife that we are supporting your little hobby

or we're going to get an angry email on the Feedback Friday inbox. You know, who else is all dolled up for you right now? The amazing sponsors who support this show. We'll be right back. Have you ever had a moment where you think, man, someone should really do something about this? Then you realize, maybe that someone is you. Well, with the help of GoFundMe, you can change someone's life. You could start a GoFund me to help a friend pay for school, fund that new community space,

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Next up. Dear Jordan and Gabe, My mother and stepfather want to give an inheritance gift while they're alive and well to me, my stepbrother, and my step-sister, the same amount of money to each. But they don't want to give that gift to my brother because he belongs to a Catholic monastery, and he would have to hand over that gift to the institution. He joined when he was 23, and as a monk, he can't get married or have children. How should my parents communicate this news to my brother compassionately?

And are they making the right decision here? signed Facing Some Early Questions about these earthly possessions. Wow, tough one. All right. Your parents want to be fair to all you guys, but they also don't want to hand over a considerable amount of money to some organization that they're not part of. Maybe they're not super fond of it. Who knows?

But then they also don't want to hurt your brother or deprive him of his fair share. So yeah, quite a conundrum here. We wanted to get an expert's opinion on this one. So we reached out to Dr. Stephen Hassan. Dr. Hassan is a licensed mental health counselor. He's been writing and talking about undue influence for over 40 years. He's on our cult episodes. He's been on the show a bunch of times.

He's also the author of Freedom of Mind and Combating Cult Mind Control, both great books. And Dr. Hassan's take right off the bat is that you and your parents should do some homework on this organization. You've got to figure out whether it's on the up and up or whether it's a little questionable. I'm not saying that monasteries are sketchy all the time, but it's possible. For example, is this one of those Catholic monasteries that believe the Pope is like satanic? How did your brother first get involved? Is he allowed to leave if he wants to?

As Dr. Hassan explained to us, the more legitimate monasteries, they have a long period where they don't pressure people to join, they encourage them to take their time, and many of them also offer exit strategies to folks who want to leave down the road, which, if that's the case with your brother's monastery, that would be encouraging. So Dr. Hassan recommends, reading up on the influence continuum and the bite model. These are two frameworks he developed to assess the methods that organizations used to recruit and maintain control over people. We are going to link to both of those in the show notes as well. Those should help you get a better grasp of your brother's monastery and the influence that they're exerting over your brother, whether it's

benign or otherwise. Now, if you come to the conclusion that there is some unethical influence going on in this organization, then Dr. Hassan's recommendation, is, do not hand over the money. But if the organization seems fair and non or uncoercive, which is the right word here, non-coercive, uncorative, which doesn't matter, it's very possible that it's totally non-uncoercive, then your parents have a tough call to make because a reasonable person could look at this situation and say, well, even if this organization is above board, it doesn't make sense for you guys to hand over your money to some group you're not a part of,

your brother can't enjoy the money anyway. So what is the point? But I could also see the argument that your brother deserves his share of the inheritance no matter what. And if he wants slash has to hand it over to his monastery, that's his right. Just like it's your right to spend it or save it or invested on, you can just blow it on cocaine and avocado toast or whatever y'all millennials are doing with your money these days. It doesn't really matter, right? But Dr. Hassan brought up another really good point, which is, hey, what if your brother decided to leave the monastery in five or 10 or 15 years, and he suddenly needs some support to reenter the world, but he just gave a hundred grand to the organization that's now in the rearview mirror. That might seem unlikely,

but Dr. Hassan actually has a close friend who was a priest for 20 years, then left, got married, so look, this is not out of the question. People can obviously change. It happens all the time. Another contingency that happens quite often, what if your brother ever got seriously sick and he needs real medical treatment? Does the monastery offer good health care? You never really think about health insurance for monks, do you? Do they have an insurance plan at all? Is there a retirement plan? Because Dr. Hassan said he's seen this happen, and it's not pretty when someone suddenly out in the cold, when their organization doesn't fully take care of them or can't take care of them. And that's where having a little money set aside could really, really help. So to get ahead of those possibilities,

Dr. Hassan shared a couple of ideas. First, your parents could put your brother's share of the estate aside for a period of time, maybe put some requirements around accessing it, namely doing some reality testing, reading books about influence and control, listening to some talks, talking to former members of the monastery, maybe even working with a counselor to make sure he really understands the organization that he's involved in, that sort of thing. Dr. Hassan is also a big fan of parents recording a video for each of their children to be played when the will is read or shared. They would basically say, I've set aside your portion of the inheritance for X number of years. want to make sure then that you're thinking for yourself. So I'm asking you to go through a few

basic reality testing processes and then you can qualify for a portion of the inheritance, say 20% of the total. And then they can see what their children do with the money. And if they don't blow it or hand it over to a questionable organization, then they can access more. So that's kind of a cool vetting process. And hey, maybe some of those requirements is that he can only receive his inheritance if he leaves the monastery. Now that would solve one problem in terms of where the money ends up going, but it actually might create a new one, which is he might feel your parents are dangling this money in front of him to incentivize him to leave the monastery. And that does feel a little bit manipulative, even if it's not intended to be. It does feel a little manipulative,

yeah, especially if the monastery is totally legit and he wants to be there. But maybe this brother just doesn't care about money, in which case, this whole thing... I mean, he's a monk. Yeah, he's a monk. Like, if that's part of his whole deal, you know, that might make this whole thing a lot easier. As far as communicating all of this to your brother, Dr. Hassan's advice is to start by talking with your parents about how they want to manage their money. And then if they decide to withhold this inheritance from your brother, they should have a very open conversation with him about how they arrived at that decision. If this were me, I would probably frame it in a way that is loving and supportive and just explains the rationale so that your brother doesn't feel like

Your parents are treating him unfairly or maybe punishing him for his choices. I would literally say something like, we love you, we've thought a lot about this, we want to treat all of you guys fairly, but we're just not comfortable with our money going to the monastery if it doesn't help you, something like that. And then hear him out and see how he responds and see if he disagrees or if he totally gets it. He might get it. Dr. Hassan also said that it would be great for you or your parents to chat with your brother about the future too. He's a big fan of asking, you know, hypothetical questions like, what happens if you get to a place where you decide to pursue God's mission for you someplace else? What do you want to have in place if you decide to start a new chapter of your life down the road or a new role or a new job? What happens if you get sick one day, to Jordan's point? You know, encourage him to imagine these possibilities so he doesn't deprive himself of the support that he might need down the line.

Whatever your parents do, though, Dr. Hassan definitely recommends working with an estate attorney to make sure that all of this is handled properly and fairly on a legal level. Yes, a good attorney is absolutely crucial. And on that note, just to take this question all the way across the finish line, we decided to reach out to Patrick Hicks, head of legal at Trust and Will, which is a digital estate planning and settlement platform. And Patrick's take, it was pretty straightforward. Your mother and stepfather are responsible for their own decisions.

If they choose to distribute money unequally, it's their money to do so. Now, that doesn't mean that there won't be hurt feelings or ruffled feathers. In his view, the emotional impact of that choice, that may very well trump the legal and financial considerations. But here's the thing. Looking at the big picture here, your parents are considering a gift to their children in order to help them advance their financial well-being. And since your brother's a monk in this monastery, that gift simply wouldn't play the same

role in his life. That doesn't mean your parents don't love him. That doesn't mean they don't support him or his calling is a monk. It just means they're making financial decisions based on the different needs of their children. It's a very fair point. And also, Patrick raised another really interesting point, which is if your parents are uncertain about this call, he said it might help to ask them how they would feel if they were to give you or your step siblings a bunch of money today and one of you guys blew it on, I don't know, a bunch of vacations or a terrible investment or Beanie babies. Tomogacchi's from the 1990s.

I don't know. Or you donate it all to Greenpeace or whatever. Would they be upset at that? Or would they accept that that was just how you chose to spend the money? Your brother, he's just made it clear in advance that he intends to pass on any gifts to the monastery. So that would be an interesting question for your parents to ask themselves, whether that changes anything. And by the way, we're not presupposing an answer here.

totally up to them and maybe to you guys. But I do think that's an interesting thought experiment. It is. I'm torn here, but personally I'm leaning toward not giving it to him, but I really do see the argument that passing it along to his monastery might be a legitimate choice on his part. And that's why Patrick's question is such a good one. Well, it's also an interesting question whether handing over his inheritance to the monastery really doesn't benefit him. Because he might say that it does benefit him in the sense that, you know, it's going to support the monastery that he's a part of. relinquishing worldly possessions is advancing his spiritual development. Yeah, but then you could support his spiritual development by not giving him anything, too, right?

Hey, you're relinquishing this, but we're going to keep it in our bank account instead of giving it to the Vatican. And then the kids who aren't wearing robes can get a little more and actually use it or the parents can just hold on to it, whatever. Also a fair point. Although that raises another uncomfortable question, which is, are these kids incentivized to convince their parents not to give their brother his fair share? because more would go to them eventually. I don't get the sense that that's part of this guy's agenda from his letter at all. No.

This family actually sounds very fair, which I love, but it is worth acknowledging. Yeah, that is important to keep an eye on. I really don't think they're trying to screw their brother over to benefit themselves, especially writing in and asking how to fairly handle this. It doesn't really jive with that. But the reality is they would get more,

potentially, if the parents withheld his inheritance. So, yeah, this guy is to make sure he's encouraging his parents to make the right call for themselves and not just because he's going to pick up another beach house or a cottage or whatever. Right. Ultimately, I think this comes down to values, your parents, your brothers, and how you guys believe this money should be used. And that is a personal decision.

So I hope that gives you a few new angles here. I really love how thoughtful you guys are being about all this. I think it really shows character. And good luck. You can reach us Friday at jordanharbinger.com. Please keep your emails concise. Try to use a descriptive subject line that makes sure. our job a lot easier. So, hey, if there's something you're going through, any big decision

you're wrestling with, or, you know, you're having trouble buttoning your bra clasps, actually, maybe that's a you problem. But if you need a new perspective on stuff, life, love, work, what to do if your close friend has a psychotic break, whatever's got you staying up at night lately, hit us up Friday at jordanharbinger.com. We're here to help, and we keep every email anonymous. All right, next up. Hey, Jordan and Gabe. I'm 66 and the oldest of nine kids. We weren't poor growing up, but there weren't a lot of extras. My parents were traditional, and because my next sister didn't come along for several years, I assumed all of the conventional girl jobs. I was 13 when the youngest was born and was pretty much his mom for his young years. My husband is great, but never

achieved much at work and retired when he lost his job during the pandemic. I don't know if I'll ever get to retire, but I am fortunate to still be able to work. My siblings and their kids are all very successful and have successful spouses from well-to-do families. They talk about things that I will never have or achieve. With the exception of the world traveler, they all have second or even third homes. Five of them had condos on the water in southwest Florida that were either washed out to sea or flooded and destroyed by Hurricane Ian. It will take a very long time to restore them. But here's the thing. I'm not feeling sorry for them. I feel awful for the people whose homes and lives were ruined, but not for my siblings. I recognize that if we weren't related, my siblings

would never have me as a friend. What is wrong with me? Do you have any advice on how to tame my envy? Signed, feeling sick after getting the short end of the stick. Oh man, this sounds like an intense childhood. Nine kids. Not a ton of resources to go around. Yeah. So you're the oldest. A lot of work fell to you. You somehow end up being the pseudo mom to your youngest brother, which is a huge responsibility for a child, and you're still working hard to this day while your siblings have had a very different experience in life. So, yeah, I can appreciate why you feel this envy now. You're looking at your siblings and you're wishing you had some of what they have. It's a perfectly normal emotion, but it is unpleasant. And I appreciate how open you're being about that because envy is

really hard to acknowledge sometimes. Although it's interesting, Gabe, I get the envy piece here, but what I'm hearing more of in this letter is actually anger. Same. I hear a lot of resentment built up here, and it is coming out in this whole Hurricane Ian thing. She's not feeling particularly bad for her siblings, and maybe that's because she envies them, sure. But I agree, it does sound more like she's angry.

And yeah, that makes it really hard for her to empathize with them. Exactly. And honestly, that anger is somewhat appropriate. She didn't have a normal childhood. She never really got to be a child herself from the sound of it. She spent a lot of her life taking care of other people. Now she's taking care of herself and her husband, which, by the way, I'm guessing that echoes the caretaking role she played as a child.

I mean, she's probably burned out. There's probably more resentment there, too, even if it isn't entirely her husband's fault. Great point. So it makes sense that she's sitting there while her siblings complain about their third beach house being washed away by a hurricane, worrying about whether the insurance is going to cover the remodel on the deck or whatever, and she's thinking, yes, sorry, I changed your diapers when I was supposed to be out riding bikes with my friends or going to prom, and I just put in a 14-hour day so my husband and I can make our mortgage payment,

which is already late, I am not about to feel bad for you. And that might not be the most charitable response. It might not be the most helpful, but it is the most understandable, in my opinion. Totally. So we can answer your first question right off the bat. There's nothing wrong with you. The anger you feel, the envy. It might be unpleasant, but it's not absolutely.

normal given the upbringing you had and also the relationship that you have with your family now. But now that she's acknowledged these things, Jordan, you know, the question is, what does she do about them? Because one of the things I really admire about her is that she doesn't just want to give into these feelings and live with them and be miserable. She wants to do something about it. Right. I admire that too. So my first thought is keep exploring these feelings, especially the anger piece, because I get the sense that that's the emotion that's harder for you to be in touch with. I'm going to go out on a limb here and say that a lot of the anger is probably directed at your parents for putting you in the position that they did, whether they meant to or not, slash had a choice or not, and probably just that you're angry at the situation as a whole. And obviously, some of the anger is about your siblings, how they've had more success on an external level.

But it's an interesting question whether they're really to blame for how things turned out. I mean, they were kids in your house too. They weren't any more aware of the dynamics in your family than you were. In one way, things worked out better for them, but that doesn't necessarily mean that they are to blame for that. And I know that that could be hard to come to terms with, but I think it's worth keeping in mind, because this is kind of poisoning your relationship with your siblings. I know what you're getting at. That's a really important point. But I also think it matters how they treat her now. Like, are they decent people who just have high class problems and they're not being very tactful about how they bring it up around her? or are they actually pretentious a-holes who like flaunt their wealth and make her actively feel unwanted?

Sure, it's hard to say. I think she experiences them as the latter, but that might be because of all this history. When she said that if they weren't related, her siblings would never have her as a friend, that really got me. That's an awful feeling. It makes me think that her family just isn't very kind to her based on what she shared, but it's also possible that they treat her just fine. and the anger she feels, that's largely an echo of these childhood wounds, and how she feels perhaps

about her life in general these days, which, again, totally fair, given what she's been through. But if that's the case, I would say, investigate that too. Trace the feelings back to their roots, figure out what is really making you angry, what is really making you envious, because you might be surprised to find that the source of those feelings isn't just your siblings. It might be closer to home than you thought. Right. Her siblings might just be the nearest object for these feelings that are very complex. Exactly. I also think it's worth pointing out that she's measuring her sibling success very narrowly.

They have material wealth, they've got some status. I get it. Those things are desirable. They do matter on one level, but true wealth, not to sound all self-help Dale Carnegie here, but true wealth is so much deeper than that. I mean, are they happy? Are they fulfilled? Do they have healthy relationships? Do they have the capacity for introspection that this woman obviously has? Do they have her sensitivity, her dedication, her work ethic? Do they care about other people half as much as she does? Wow.

Yeah, that is such an important point. She's looking at her family and she's envying them for having these champagne problems, right? But I promise you, having a beach house, traveling the world, yes, very fun. But those things alone do not make you happy. They don't make you complete. And again, like Jordan, I don't mean that. in some Instagram quote kind of way. The research actually bears that out.

I got to pause you right here. I don't even know if we can say Instagram quote anymore. Now it's a TikTok dance while the text appears over the video and you're pointing at it while you're doing a really cringe dance. I feel like I just saw that video. And I really don't mean to sound like that video, but that is actually true. On that note, I also want you to read an article we wrote about this exact topic. It's called Want to Overcome Envy.

Make It Your Teacher. This is an oldie-buddy-buddy. We get deep into the psychology of envy in that one. We talk about how to break it down and use it to become a better person. And I think that'll be a great read for you right now. We'll link to that in the show notes for you. If you unpack these feelings, even a little bit, I really do think they'll start to shift.

And then you can decide what to do about them. Maybe you approach your siblings in a new spirit. Maybe you pull away from them a little bit. Maybe you remember that their problems are not a reflection of you. Maybe you encourage your husband to go back to work so you're not recreating a situation where you're taking care of somebody else at your own expense. There are a lot of pieces to this experience. So just try to pull them apart as best you can. So hang in there, be kind to yourself, get curious about this stuff.

And here's a hug from Hurricane Free California. You know what'll make everyone else in your life envious? The amazing products and services that support this show. We'll be right back. If you like this episode of Feedback Friday and you found our advice valuable, I invite you to do what others smart and considerate listeners do, which is take a moment and support our amazing sponsors. All the links you hear, all the discount codes you hear, they're all on our deals page at Jordan Harbinger.com slash deals. You can also go to the homepage over at Jordan Harbinger.com and search for any sponsor using the search box on the website as well. Thanks so much for supporting those who support us.

It does keep us going, and it makes it possible to continue creating these episodes week after. week. All right, back to Feedback Friday. Okay, what's next? Hey guys. I'm 17 years old and I'm in high school in Nairobi, Kenya. Ooh, wow, amazing. Both the age and location. Love it. Go on. I was appointed class prefect last term and I was very eager to shape up my underperforming class. I strove to do my best, reading leadership books, trying to improve myself, but I feel like a few are not willing to follow me. They've just accepted their condition. Some classmates, are now committed to making my life a living hell. If I reprimand them, they'll steal my property. The school administration can't really do anything since there's no evidence. My friends want me to

drop the post since I'm getting seriously psychologically hurt. But I can't transfer to a different school now and I want to shape up the class to bolster my chance of admission to MIT, which is my dream university. What should I do? Signed, Embrace my inner Tracy Flick, or find a better way to crack the whip. Gabe, you're going to have to explain that Tracy Flick thing. Okay. Have you seen the movie election? Is that Reese Witherspoon? I don't think I've seen it, but I've seen, you know, the trailer or something.

Got it. Such a good movie. I actually have to rewatch it. It's been a long time. It's really good, really bizarre. It's basically about this like type A, you know, hyper competitive girl who desperately wants to be like the president of the school and she's just like kind of a monster. And the whole election devolves into this like insane campaign where the whole school is pitted against it.

It's great. movie, but I don't know, just something about this guy just reminded me a little bit of Tracy Flick. The intensity there? Yeah. This is an interesting situation. Look, you sound like a very ambitious guy. You're obviously very driven, and I'm sure you're going to go very far in life. I wouldn't be surprised if you end up running for office or leading a company or something

one day. It's exciting. But I also hear you that this approach is taking a real toll on you. It sounds really hard. I'm sorry that your peers are retaliating against you now. I experienced maybe the very diet-light version of that myself at your age, and I just, I know how hard that is to cope with. So first of all, I think some of this is happening because not everyone responds well to personalities like yours, especially people who are not as disciplined as you seem

to be. And that's especially true in high school, where social hierarchies and, frankly, adolescent BS play a huge, outsized role in people's opinions. Some of what you're struggling with sounds just like high school stuff that is markedly absent from the adult world in most cases. At the same time, though, I do wonder if what you're starting to realize is that your leadership style just is not working the way that you hoped. You're reprimanding your peers, you're pointing out their flaws, they don't seem to appreciate that, and your reasons for whipping this place into shape, well, they're largely about advancing your interests. You want to go to MIT, so you're stepping up. Bravo, but my question for you is, are you the prefect who's encouraging people to be their best

selves, or are you the prefect who's maybe kind of sometimes a little bit of a tyrant for his own ends? I think it's probably both, but the latter might win out sometimes. So this whole ordeal that you're going through, it might be your first big lesson in leadership and power. To get people to change, you have to inspire them to get better for themselves, not just because you're telling them to or because it'll help your chances of getting into college or because you're going to tell the assistant principal or something like that. You have to build relationships with people that go deeper than just your role. You have to be a good peer to them. You have to be respectful and humble, fun to be around's not going to hurt. You can't just be the drill sergeant who's always handing out

dress code citations or whatever. I mean, you don't take that crap from a teacher. You're going to take it from some fellow student. Give me a break. And you have to figure out what motivates other people, what their interests are, and then see how those line up with yours. Because what you really want is for your peers to identify with you, right? But to do that, you have to be willing to do the same with them. And it's really hard to earn people's loyalty and respect when you're only telling them what they are doing wrong. It can come across as annoying.

It can be a little demoralizing. It's nitpicky, especially in high school. Being a hard ass has its place, but it just can't be the only arrow in your quiver. So that's my take. If you want to get on better in school and you really want to lead people in the future, you have to balance your authority

with kindness, flexibility, empowerment. And I know it's kind of funny to be breaking down a high school politician's playbook like this, but everything we're talking about, it's the exact same thing I would say to a 45-year-old entrepreneur or senior manager or executive. I'm just excited that you're getting to learn this

so young. I think that's amazing. This challenge you're going through now, I know it's painful, but it's also a great opportunity. Be open to adjusting your style, and I know you'll take some great lessons into the rest of your life. And good luck. All right, next up. Hey, Jordan and Gabe. I'm a partner at a very large law firm where I've worked for six years, and generally the firm has been good to me and offered me many opportunities for success. Recently, though, I've been treated like a doormat by those above me. This is par for the course for people at and below my level. My other colleagues have the same experience, but they choose to just stay silent or quit. Lately, I've been speaking up more when I feel disrespected. I go directly to the person in question, and I tell them that what they've said or

done is inappropriate, and that I don't appreciate it. Most of the time I get an apology, but I don't feel the apologies are genuine. My direct supervisor treats everything like a joke, and I think that's a way to make it seem like I'm just being sensitive, when in fact I'm actually pretty thick-skinned. I've considered looking at other opportunities, but I know that a change might be a setback, financially and opportunity-wise, and I would have to start all over. What advice do you have for someone in my situation? Should I stay, put my emotions aside, and ignore the haters? Or should I go and hope that the grass is truly greener? Signed, a barrister, fed up with these disparagers. Oh man, letters like this really make me grateful to be out of the law.

I bet. Some of the personalities you encounter in that world are just, yeah, they are not easy. The fact that other partners at your level deal with the same thing, that you're pretty thick-skinned in general, that means this probably isn't a you problem. It's a culture thing, and that sucks. The good news is, it sounds like you're learning to speak up when it's necessary, and you're doing that the right way by talking to these people directly. That is not easy to do, but it is the mature thing to do, and I commend you for that.

This supervisor who kind of laughs it off when you tell them that something bothered you, that could be them trying to signal that it's nothing personal, or that could be them not taking you very seriously. Hard to say. But it would be nice if they could say, I can see that you're upset. I'm sorry it I rubbed you the wrong way. I didn't mean anything by it. Maybe our wires got crossed. Let's talk it out. And even if you were being a little sensitive or reading things, you'd at least feel heard. But again, tall order asking a senior law partner to actually, you know, have feelings. So here's my take. If being treated this way is just business as usual at your firm, if these people are making you miserable, like in a way where you just dread

go into the office, then yeah, I would consider looking around. I found it interesting when you said, I know that a change might be a setback. Because you're right, jumping to another firm could be a setback, but it also might not be a setback or not an insurmountable one. And you can't know that for sure without seeing what opportunities are out there. Because first of all, just meeting people at other firms, casually interviewing, that might give you some freedom, maybe even a little inspiration, and that might help you cope with these tough personalities at work, just knowing that you're not stuck. But also, I wonder if you're just being a tiny bit rigid here, or if you're imagining worst-case scenarios because it's all neat, abstract. Because if you met some cool people at another

firm, if you found a more positive culture, you might be like, wow, okay, these are my people, this firm is great. Yeah, I kind of have to start over, but I'll be starting over in a place that actually makes me want to do my best work, and I can catch up. But again, I want to challenge you a little bit there too, because you're a partner. You have a track record, probably a book of business. I'm assuming you're pretty good at what you do. So I'm not sure if you would be, you would starting from scratch if you left. You might be starting from scratch in terms of some relationships or clients, but that doesn't mean that you're absolutely back to square one in your career. It just means you'd have to put in some work to get up to speed and build your cred in a new place. And look,

that's okay. In fact, if you're motivated, it can be invigorating and fun. Totally agree, Jordan. Also, when you said that any change might be a setback, I think it's important to remember that also sticking around in a negative workplace, that's a setback too, right? You might be jamming on your cases, you might have an established reputation, but you're still dealing with these senior partners who seem to treat you pretty poorly. So it's like, which setback would you prefer? The place that's familiar, that gives you opportunities, but also makes you miserable, or a new firm that's unfamiliar at first, but that values you and treats you well, you know? Yeah, good point. In my book, life is just too short to be miserable, and she's too young to just resign herself to affirm that

makes her unhappy. So my advice is, if you stay put, find a way to cope with these annoying partners, maybe learn how to let this stuff roll off your back a little more, and look for ways to change the dynamic with these people if you're playing a role in all of this. But if they won't change, you just want to shake things up, I would start casually looking around. Just be open, be curious, try to connect some dots. You don't have to leave your job. No one is making you do that, but you have literally nothing to lose by talking to people and everything to gain. So at a minimum, make a decision to be open to the possibility. Sometimes that's half the battle. And good luck. Hope you all enjoyed that. I want to thank everyone who wrote in this week and everybody who

listened. Thank you so much. Go back and check out General Robert Spalding and Angela Duckworth, if you haven't heard those yet. Want to know how I managed to book all these great people and manage my relationships using systems, software, tiny habits, check out our six-minute networking course. That course is free. It's over on the Thinkific platform at Jordan Harbinger.com slash course. I'm teaching you how to build relationships before you need them, manage them in just a few minutes a day.

Dig that well before you get thirsty. And look, these drills, they're designed to take just a few minutes per day. This is the type of habit that we can ignore only at our own peril. This is the stuff I wish I knew 20 years ago. It's not fluff. It's crucial. You can find it all for free.

at Jordan Harbinger.com slash course. I'll link to the show notes for the episode at Jordan Harbinger.com, transcripts in the show notes, advertisers, deals, and discount codes, all at Jordan Harbinger.com slash deals. I'm at Jordan Harbinger on both Twitter and Instagram. You can also connect with me on LinkedIn. You can find Gabe on Instagram at Gabriel Mizrahi or on Twitter at Gabe Mizrahi. This show is created in association with Podcast 1. My team is Jen Harbinger, Jace Sanderson, Robert Fogarty, Ian Baird,

Millio Campo, Josh Ballard, and of course, Gabriel Mizrahi. Our advice and opinions, they're our own. And I'm a lawyer, but I'm not your lawyer. So do your own research before implementing anything you hear on the show. Ditto Patrick Hicks at Trust and Will. If you want to learn more about those guys, visit trust and will.com, which is a great domain, by the way, to learn more and get started on your will or trust today. And remember, we rise by lifting others. Share the show with those you love. And if you found the episode useful, please share it with somebody else who could use the advice we gave here today. In the meantime, do your best to apply what you hear on the show so you can live what you listen and we'll see you next time. You're about to hear a preview of the

Jordan Harbinger show with Pickpocket King Bob Arno. Pickpockets don't talk. They lift and do everything silent. I have spent 20, 30 years befriending or getting very, very close into how they work. They can be put into three or four different categories. The skillful ones that are ashamed of what they're doing, then you have the youngish one who couldn't care less about some moral compass, and then you have the ones who get out of work and some older guy is saying, hey, I want you to be part of the team. They weren't thinking of going into crime.

There are many, many levels of pickpockets. some are very aggressive and angry. The thieves picks it, but pickpocket never holds, so he passes it on to a partner. So if the police catches him two seconds after, he's clean. There's nothing on him. And the way there was none of this usual pickpocketing move, the elegance was unbelievable.

I had to look at it at least 10 times before I could see what the hell did I see? And some of them are very charming, by the way, and that goes for the territory. There's a very good smile and like a ping pong very quickly, boof, boom, boom, back and forth. There's nothing slow. If you measure me against the very, very best in each country,

I'm going to be a couple of pinhole below. The good pickpocket respect me for my skill, and they say, Bob, I don't understand how in the hell did you get this skill? They are in all. To learn pickpocket tricks of the trade and how to protect yourself against thieves, pickpockets, and scam artists, check out episode 530 of the Jordan Harbinger show. This episode is sponsored in part by Something You Should Know podcast. Finding a new great podcast shouldn't be this hard, so let me save you some time. If you like the Jordan Harbinger show, you'll probably like Something You Should Know with Mike Carruthers. It's one of those shows that makes you smarter in a practical, useful way. Same curiosity vibe we go for here, just in a fast-focused format. Mike brings on top experts and asks the exact questions,

that you'd want to ask, and the topics are all over the place in the best way. Recently, they've covered things like why we care so much what other people think, the benefits of laughter, why sports fans get so invested, and what makes people like you or not, the through line is always the same. Smart ideas you can actually use in real life. Something You Should Know has been featured in Apple's shows we love, and it's got thousands of five-star reviews because it's consistently interesting. So if you want another show that scratches that I want to understand how people in the world really work, itch, search for something you should know wherever you get your podcasts.

Look for the bright yellow light bulb and start listening. You can thank me later.