Jo Ellis Served Her Country. Then They Made Her A Target.

0:00Ryan Holiday: This year is going to be the 10-year anniversary, not just of the Daily Stoic book, but dailystoic.com. The email, the podcast, all that stuff. And I don't think we would be standing here 10 years later if it weren't for Shopify. Shopify has been the back end of so many things we've done, from the New Year New You challenges, to the medallions, to posters. Even right now, if you're going to buy a signed book from me, you're going to be checking out through Shopify at dailystoic.com. or if you're buying something from Daily Dad there, or if you come to the Painted Porch, we even use Shopify at point of sale in the store.

0:33Ryan Holiday: And if you've been sitting on a business idea, Shopify makes it easy to make that happen. You've got everything you need to start selling and Shopify handles the setup and the checkout and you can focus on growing the business and they've got all the tools to help you with what you need, which is why Shopify powers millions of businesses worldwide from household names like Mattel and Gymshark to small businesses just getting started like Daily Stoic was not that long ago. with shopify nothing stands between your idea and real business so go make it one start your free trial at shopify.com slash stoic that's shopify.com slash stoic to start your free trial i'm on the road for these daily stoic talks i'm doing i started in seattle my family and i drove all the way down now i'm in san francisco we're in sacramento tomorrow i've actually been booking houses on airbnb all along the way we stayed in this awesome one in mendocino last night.

1:22Ryan Holiday: We stayed in a lovely one on the ocean in Bremerton, Washington. It's been awesome. And that's usually how we stay as a family when we're traveling. We book houses or apartments on Airbnb. But what a lot of people don't know is that when I first started as a writer, I used to list my house on Airbnb. My first house, this little house in East Austin, we would book it out when we were out of town, which is what Airbnb is so great at. And then when we moved out to the country, I would write at it during the week and book it out on the weekends. And that's how we helped cover the mortgage. That's how I was able to make the transition from a marketing person to a writer.

1:53Ryan Holiday: Wherever you live, but especially if you live in a city that's hosting a bunch of events this summer or you're traveling, you should think about listing your house or apartment or condo on Airbnb. It might be worth more than you think. And you can find out how much at Airbnb.com slash host. Welcome to the Daily Stoic Podcast, designed to help bring those four key stoic virtues, courage, discipline, justice, and wisdom into the real world.

2:25Ryan Holiday: Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. There's an old joke on the internet that says every day there's a trending topic on Twitter and your goal is to never be that topic, right? You might think you want everyone to be talking about you. You might think you want the whole eyes of the world on you, but if they are, it's almost certainly because something really bad has happened or you screwed up in some huge way or things are about to get real bad real fast. Like imagine going to sleep and you wake up and you're trending nationwide, but it's because everyone thinks you're dead.

3:06Ryan Holiday: People are total strangers or posting your photo. They're tying you to this tragedy. They're politicizing you and your identity. They're telling stories and lies about you that aren't true. They're incredibly angry. Imagine it's so extreme, so crazy that you have to record a proof of life video just to make sure the world knows you're still alive. And in the process, try desperately to defend your name. And that actually happened to the person that I'm talking to today. Jo Ellis is a Black Hawk helicopter pilot. She was in the Virginia Army National Guard for many, many years when she was suddenly falsely accused in January of 2025 of being responsible when that tragic, terrible airliner crash happened over Washington, D.C., right?

4:01Ryan Holiday: A Black Hawk helicopter crashed into a commercial airliner over D.C. and 67 people lost their lives. And shortly after this happened, And Ellis, who is transgender, was accused of being that pilot. And she was accused of this for no other reason than bigotry and sort of rage profiteering. People wanted to somehow take this tragedy and lay it at the feet of a minority. And then specifically the feet of a person, a veteran, hardworking member of our armed force. So they wanted to put it on that person to score internet points, to prove a point. I don't know. But anyways, this rumor spreads all over the internet.

4:47Ryan Holiday: She becomes this trending topic. She starts getting hate messages and death threats. Imagine you get death threats after you are falsely accused of being dead. There's a whole bunch more to the story as we're going to get into the episode. This is not really about this current event. It's about this incredible and fascinating woman who was also forced out of the armed forces as a result of what happened. But that's only a facet of this fascinating life. She sort of goes into hiding, handles a bunch of stuff in her personal life, but then reemerges as a stand-up comic. Lo and behold, it turns out she's hilarious.

5:22Ryan Holiday: If you saw her on Kill Tony, my intro is getting long, so I won't play it. But it was really, really funny. And you should definitely check it out. I'll link to it in today's show notes. So in this episode, Joe and I are talking about this crazy experience. I was fascinated to ask her a bunch of questions about SEER training. That's survive, evade, resist, escape, which is the training that Stockdale went through, which I'm writing in my book right now. what it means to come to your breaking point, how you come to a realization about your identity. We talk about our experience being a trans person, being a trans person in the military.

5:56Ryan Holiday: What happens when your private life becomes a public debate and what service means when you are suddenly a headline? I think you're going to really like this episode. You can follow her on Instagram at Joe Ellis. Really go see her perform standup. Enjoy this episode and follow Joe. She's a fascinating person to be tracking. So did you always want to be a helicopter pilot? Yes, I wanted to be a pilot. I wasn't sure about helicopters, but definitely when I was little, looking up at the sky, seeing planes fly over, very much wanted to be involved in flight. What took you to helicopters then? Black Hawk Down, the film.

6:33So the Ridley Scott film was just, not that I wanted to crash them,

6:37Ryan Holiday: but you know. Yeah, that's the opposite. But just seeing them and seeing that movie and that came out around the same time that I was like 13. So like it was kind of like that formative years of just like I want to be a part of something greater and I want to fly. And those machines just looked incredible. And so you started as a mechanic though, right? I did. I did. Yeah. So I started as a helicopter mechanic. My recruiter told me that's the best way to become a pilot is to learn everything about the helicopter. Not sure if that was entirely accurate. Yeah, I was going to say that sounds like something you would tell like an 18 year old who doesn't know anything because you're trying to meet a recruiting quota.

7:12For sure. I mean, it's definitely easier to recruit someone as a mechanic enlisted than it is to recruit them straight into flight. But there was a pathway to go straight to flight. I just didn't know it. But it worked out for the best because I did get a good understanding of the helicopter and a lot of experiences. And I ended up getting rejected from applying for flight school. I think I applied three times, got rejected twice. So the third time is when they finally accepted me.

7:36Ryan Holiday: When you were in high school, did you always plan to join the military? Was that like your career path? Was that common in your family? It was like definitely in my mind, like service, you know, is in my blood and my great uncle fought in the Battle of the Bulge. And my grandfather was in the Navy during World War II. My cousin is Admiral Jim Ellis, who is now at the Hoover Institution. So like huge line of history and just always wanted to serve, but wasn't sure how. Yeah. My brother served in Iraq in 03 as a tank driver. He was active duty. And so that kind of taught me like, oh, I don't think I want to be active duty.

8:12I don't know if I want to do that all the time. And so that's when the National Guard came up as an option. And I was 19 years old and, you know, struggling to pay for college and always wanted to serve and just driving down Interstate 64, seeing Blackhawks fly over me and just like, yeah, I think I want to do that. Like, I want to fly. I want to be a part of something greater. and it all just kind of hit at the same time.

8:34Ryan Holiday: So what did becoming a mechanic look like? What was that path? So I was like 15 weeks at Fort Eustis in Newport News, Virginia and learning just how to work on them. So I started as a structural mechanic, learning how to like shoot rivets and bend metal and fabricate parts and patch holes and things like that, lots of composites and stuff. And as soon as I got out of school, I immediately got deployed with my unit to Iraq. Yeah. And they asked for volunteers to be door gunners. Right. So I was like, sure, I'll do that because that'll put me in the aircraft. A little more exciting. Yeah, it'll put me in the aircraft that's closer to the front seat.

9:10Right. Right. So my whole idea is like, how can I get closer? And I mean, what 19, 20 year old doesn't want to operate a machine gun out of a helicopter while it flies, you know?

9:20Ryan Holiday: So that's what I did. And that was a blast. And, you know, flying eight hour days, you know, just over the desert doing that whole life. But you're doing two jobs in the same. Yeah. So I would, one day I would fly, the next day I would work on helicopters in the hangars. And then the next day I might be on the flight schedule again, I would fly. So kind of leading to two different jobs at the same time. And you're probably just starting to know this machine like inside and out. Inside and out. Yeah. All at the same time. And in the meantime, I'm still maintaining a civilian career because you're guard.

9:55Right. You're part time. So I fell into E and just started doing like technical support, like help desk and started climbing that ladder too. I originally wanted to be a video game designer, but so I went to ITT Tech, which is funny because that school doesn't even exist anymore.

10:11Ryan Holiday: I remember all the commercials as a kid. Yeah. Yeah. And they're like video game design degree. And I'm like, yeah. So I learned a lot about like Adobe Creative Suite and just like graphic design type stuff and dropped out of that pretty quickly just because it wasn't going to jump me into like a paying career. but tech support did. So here I am fixing computers one day, the next day I'm flying in a helicopter and then the next day I'm repairing helicopters. And then what's the path to actually getting to fly? So the path to flight is you have to put together a flight packet, which is like a huge application process.

10:43You have to get recommendations from people and then submit that to the military. And then you sit for a board and they interview you. And then if they give you the blessing, then you get to move on to flight school. So I did that twice, got rejected two times, ended up going for another military specialty, which is like another specialty on the Blackhawk, learning that job and made it to staff sergeant, which is an E6. And I was like around 12 years of service. I was like, you know, I think I'm going to get out. Like I never made it to flight. I didn't think it was going to be in the cards for me.

11:18And then on a whim, I decided to throw my packet together one more time, submit it. And then they accepted me. So I was like, oh, I guess I'm staying in this for a long term and I'm going to go to flight school. And that's 18 months of training in lower Alabama at Fort Rucker. And that involves warrant officer school, which is kind of like basic training again, but also with college level courses. So like a lot of military history courses, things like that, military writing. And then once you do that, you move on to SEER training, which is a very brutal three weeks of training. And then after that, you go to primary flight training.

11:56So once you do all that, then you can actually start flying the helicopters. And you start out in a smaller aircraft, the Lakota, which is a UH-72 Eurocopter frame. And then you move on to your what they call go-to-war aircraft, which for me, because I was guard, I already knew what I was going to fly. There was no like selection process for that. I just knew I was going to fly Blackhawks because Virginia only has Blackhawks. So that's the only thing I can fly. And so then I went to Blackhawk course and then finished that. So about 18 months later, I was a pilot. And this was like around 31 years old, 32 years old.

12:30How many hours do you think you have in a Blackhawk? Not a whole lot because I finished flight school in 2022. And then I flew for about a year with my unit. So I've got about 300 hours total as a pilot, about 100 as a crew member before. And then...

12:49Ryan Holiday: Oh, right. Because you're National Guard. So you're not in it every day. Yeah. 100 hours a year is typical for even for active duty, like 100 hours a year, you know, it's like your standard minimums for hours. And it's not like you just have one at home that you practice with. They don't let me take it home, unfortunately. But yeah, so unfortunately it was cut short because of the military ban and everything. and so like, yeah, I couldn't fly anymore. I've been actually reading a bunch about SEER training. It's fascinating because I'm writing about Stockdale and he obviously, he not just went through it, it was like a formative experience in his life, which it sounds like it was for you too.

13:24Oh, it's, yeah. Yeah, I don't know how much you dug into my story, but SEER training was a huge part of my life. Tell people what it is

13:31Ryan Holiday: because I don't think most people know. Yeah, so it's survive, evade, resist, escape. Yeah. Yeah. And it's a classified school. Parts of the school is classified. So there's only certain things I can discuss, but like, there's a lot of classroom. There's a lot of how to make a shelter, like Boy Scout type stuff, which is all unclassified, which is fine. Like what you would do if you crashed. Yeah. If you crash, like how are you going to get water? How are you going to get, make sure it's drinkable? Like what kind of plants can you eat? Like very basic type stuff that's good to know. But then there's other aspects of it too.

14:03There's like a POW aspect of it and learning how to resist when you're in capture. And then of course, some of the more dangerous parts can be the escape part or the rescue. And so it's learning how to, if you're going to escape, how are you going to do that? And then if you're going to be rescued, like, how do you not get shot during the rescue process? Like as things are going down. So good stuff, like really good stuff. I would never want to do that school again, but it was probably the best school ever. That's also where I had my epiphany that I was suffering from gender dysphoria. There's a point in that training and you are placed in like sensory deprivation.

14:45Ryan Holiday: They put you in a box, right? Yeah, a box. Yeah. It's more like a closet. So ironically, it's like I came out of the closet in the closet. But no, it's like you could like do like this, you know, like there's enough room to like squat and move around. But anyway, you're in there. It's probably to what mimic like being in an isolation. In a cell. In a cell, yeah. And so you're in there eight-ish hours, 12 hours. You're not sure, you know. You know, you're standing up most of the time. They're blasting Yoko Ono over the speaker, which is its own form of torture, you know. They're trying to break you, right?

15:22In a way, like I don't know exactly what they're trying to do, but.

15:24Ryan Holiday: Or mimic what someone who's trying to break you would do. so you can be familiar with that if that were to ever happen. So stress inoculation training is another way they define it. And there's psychologists like blended into the role play watching, you know, like it's very controlled. So they're not like just messing with people, but it has to be one of the most interesting like points of data the army has is everyone who goes through the school and what kind of data they might gather from that. Right. But yeah, so I was in there and like, I, I think what had happened, my best way to describe it is you're, you're very tired and very hungry by the time you get to this process, you know?

16:05And so once you're in there, it's like, you have no defense mechanisms mentally, physically, like you're, you're, you're kind of just depleted. And I think it took that much to be in a position where I wouldn't just push this away or say what it wasn't. Justify that it couldn't be me, that I couldn't really be having these things. And I describe it like an old slideshow, like just images flipping through, zipping through of all these things in my life of gender dysphoria and just running from it and all of those things. And it's where I had my epiphany that like, oh, that's what this thing has been this whole time, my whole life that I've been like struggling with that.

16:51I didn't want to, I didn't want to name it. I didn't want to face it. And I wasn't even sure what it was because I grew up in a, in an environment where, you know, very conservative Christians. So it's like, I didn't even have language around it. I didn't know what gender dysphoria was at the time. So I guess they broke me in a different way.

17:09Ryan Holiday: Well, I was going to ask you that. I have a bunch of questions about this because I've been thinking a lot about it, but But like, I guess that would be one sort of critical read on it would be like the training was dramatic and it caused some sort of break in some way. And that's what the training is supposed to reveal. Do you know what I mean? Like, did you consider like, hey, maybe I didn't discover something about myself. Something went sideways. I did think that at first, because when I got out of the training and you eat a nice meal, like I went to Chick-fil-A afterwards. That's where I went.

17:44You can't deny the Lord's chicken. So I went to Chick-fil-A and just like had a milkshake and chicken nuggets and just like sat with it. And I was like, you know, that was just some crazy episode, you know, because I was also like in the woods at one point before getting into the PW situation. Like you're so tired that like you can start hallucinating, right? Because it's dark and there's shadows and it was raining and lightning one night. And I was just like, did I just see somebody? And, you know, there's all these jokes about, oh, when you're in Sear, you'll see like, you know, the ghosts of the forest and like all these things.

18:18And so I was trying to once again, once I had kind of come to my senses, trying to chalk it up to this thing that they can't be. Right. and a few weeks went by and it was still festering and so i went for the first time i went to see a therapist about it and i said hey look this is this thing that happened but then here's all these things that i thought of during that time that like feels like true yeah and they said yeah that's gender dysphoria and i was like really they're like yeah i'm like but i've i'm successful Like I've done this, I've done that.

18:54Ryan Holiday: This is your VA doctor, right? This is not a VA. This is a private. Yeah. So as pilots, you learn not to do certain things medically. You know, when you're just asking certain questions, then you're not quite sure because of the impact it can have on your flight physical. And so this, since this wasn't like a formal diagnosis or anything, it was just like a counseling session. But that's where I kind of started exploring it. And then once I realized that's what it was, because I was in the middle of flight school, I was like, well, I definitely can't get a formal diagnosis right now. I can't go get it treated because then I'll be pulled from training immediately.

19:30And I don't even know if this is really what it is. I still hadn't really accepted it. And then I told my wife immediately after. And yeah, it was rough. I still managed to get like 90s and above on my flight evals and graduate. I was really good at compartmentalizing. And flight training is so demanding of you entirely that it was actually a break. I would go to class or I'd go and fly with my instructor and I couldn't think about anything else. But that was kind of a way to manage processing it.

20:02Ryan Holiday: So are you actually alone in the like you're you're obviously alone in the box. But when what I was reading about the person I was researching is that they would put them in the box and then they're sort of like shouting things at them while they're in the box. Like, because they're trying to help you sort of learn how. So he remembered they were shouting, like, get your get your head out of the box over and over again. What he took that to mean is like, you have to sort of physically be there, but mentally you can be wherever you want. And so one of the ways they'd worked him through dealing with the long hours of being in isolation was to go on these sort of mental journeys.

20:40Ryan Holiday: And they had him like, pretend you're eight years old and you're walking to elementary school. And you would go on this sort of mental journey. It sounds like you went on quite a mental journey. I went on a ride, yeah, for sure. I've heard people say psychedelics are similar. like the type of state I was in. Yeah. Because it wasn't scary, like having that epiphany. It was like as if puzzles were clicking. Like it was just like, oh, like, gosh, that makes sense. But that can't be at the same time. What were the pieces that you're thinking about? Like, because I do think people think that we have epiphanies in life and it's like you just get struck by lightning.

21:20Ryan Holiday: Yeah, not quite. Because what it usually is, and this is also, I think, people think like scientific discovery is, again, like lightning striking. What it usually is, is you've had all these pieces for a long time and you just didn't know what they meant or how they fit together. And then the epiphany or the moment is where suddenly you see it or you see a glimpse of what it is and then you know the work you have to do to put the pieces together. Right. It's like you take a bunch of clues and you scatter them and then reassemble them. And then all of a sudden it's like, oh, and now it all makes sense.

21:48Right. Like, I guess old like mysteries, you know. And so, yeah, that's basically what it is. Like the pieces were dressing up in my sister's clothes at five years old or being very envious of women and not realizing, confusing it with attraction. So attraction and envy is sometimes very similar. And so it's not understanding that. But then also like all throughout the years, like, you know, just having these moments where trying to blend in with whatever I thought I was supposed to be as a man. Yeah. And trying to emulate that and realizing like even other people could see it wasn't authentic.

22:29And it would come off as like, oh, you're being awkward or oh, you're this or that and or being accused of being gay, even though I never was interested in men. So it's like people were seeing something that I wasn't seeing. Right. Right. And then also internally having this, this, these feelings that like, oh, but the only example I know of that is like Buffalo Bill and Silence of the Lambs or like these terrible depictions. Well, I'm not that. So it can't be this. And then, of course, my moral compass was very much based in Scripture, which is these are sinful, terrible things that you're thinking of or wishing to be.

23:09Ryan Holiday: Even though that's not actually in the Scripture. Sure, right. But just whatever the people that you defer to tell you what was supposed to be. Yeah, that it must be sin, right? Like, it must be sin to somehow I'm broken to be thinking these things and other people don't think these things because I'd never met anyone who ever said some other things. But then, like, even other things. I remember, like, as a teenager, like, planning a birthday party with my best friend. And I was like, oh, it'd be really cool to do, like, karaoke. And, like, all the guys can sing girls songs. All the girls can sing guys songs.

23:43And he, like, deadpan looked at me in the face and said, why would we do that? Right. And in my head, I'm like, why wouldn't anyone want to do that? Sure. Why wouldn't anyone want to? And then, yeah. So stuff like that, like over the years.

23:55Ryan Holiday: And that kind of stuff just came flooding back to you in that box? Yes. Like all these images and feelings and phrases and things that people had said and things that I had said, you know, very much would just be like, surely everyone wishes they could be the opposite sex. Like that's a normal thing. And maybe some people like entertain that thought for a second, like out of curiosity, but I would dwell on it. I would obsess over the idea of it. Like, how cool would that be, you know, to be this other thing that I feel more closely aligned to? Yeah. Hey, it's Ryan. I'm on the road right now doing talks all over the country.

24:36Ryan Holiday: I love traveling. I love going to new places. The thing I don't like about it, though, is I don't get to sleep in my bed at home, which I like not just because it's home, but because I have an eight sleep on my bed. I've had an eight sleep on my bed, I don't know, five years. I love it. My wife loves it. We love it because it cools the mattress. It heats the mattress. You can have different sides cooled at different temperatures. It's even how I wake up in the morning. Instead of an annoying alarm clock or that horrible sound on your phone, it lightly buzzes you awake. And then when you're up, you want to turn it off, you just tap the mattress.

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27:03Ryan Holiday: slash stoic. It's like sort of like your world gets rocked in there. Yeah. And then, and then you're like, I should probably talk to someone about this. Yeah. Yeah, for sure. And of course, as we're leaving that school, there's a psychiatrist, psychologist, they're like, oh, if you ever need to speak with them, this is the person you talk to. And that's the last person I wanted to talk to about it. Because it's like, if, because the fear was, if I say these things, then I will be immediately pulled out of training. I'll be immediately like, which probably wasn't true. Right. But it's the fear and it's the story every pilot tells you is like, well, whatever you do, don't tell the doctor, which is not great for aviation safety and its own, but at the same time, it's archaic and they disqualify really good pilots for no reason.

27:45Ryan Holiday: So. And historically, disqualified people for a bunch of. A bunch of stuff. Right. Like that's not that big of a deal. Right. And so, yeah, it's, it's, it's tough to kind of go it alone knowing like, I can't really talk to my family about this. Like the only person I told was my, my wife and that was rough in itself. Yeah. That feels like a, that feels like a tough conversation. Yeah. Yeah. Have you ever told your wife something like that? Not yet. Yeah. Yeah. That was a hard process. At first it was very much, you know, like you did this to me, you tricked me like, you know, like betrayal. And of course justified.

28:27And you guys

28:28Ryan Holiday: been together a long time? Yeah. Yeah. About, about 10 years. So, and then after a while of me telling myself that I'll just, I'll just keep living life this way. I've done it for this many years. I can keep doing it. At least I know what it is now and I can, I can treat it without having to transition and things like that. And about a year or so in a couple of years into that, And she pulled me to the side and said, hey, look, I can see this affecting you and you need to do whatever it is you need to do for you, for your health. Wow, what a gift. Yeah. And she said, you not worry about me. Like, I'll still be there for you in every way I can.

29:08Maybe not in the same way, but I won't forsake you. And I say that she didn't give me permission, but she set me free. Right. Because there's no way I would have chosen to do that to her. I would have just suffered.

29:23Ryan Holiday: Yeah. And the dark side of gender dysphoria that's untreated is the indifference to living. What do you mean by that? I knew that I wouldn't kill myself, but I was totally okay if something killed me. That's not a great attitude for a pilot, probably. No. Yeah. And it was never other people's lives at stake. So it was always one of those things where like, no, like I need to do this for them and never occurred to me. But at the same time, like I'm in the car by myself driving and it's like, oh, if someone pulled out in front of me, like that wouldn't be so terrible. Right. But I would never seek it.

30:01It's not like I would ever do it. But it was one of those things where like I had accepted in a darker way that if I'm dead, I'm dead. And that was tough to get through. Because that's like taking the soldier's acceptance of death and pushing it to a point of being, like I said, indifferent, indifferent to life.

30:23Ryan Holiday: The soldier's indifference to death is in service of something or someone. Exactly, exactly. And what you're describing is more like - In service of myself. Yeah, or resignation. Yes. Yeah. Yeah, not giving up, but like, I'm like, oh, this kills me, like, there's an upside to that. Yeah. Maybe. Well, because it resolves an irresolvable conflict in your life without you having to do anything. Well, who doesn't like that, right? Yeah. It's the ultimate lazy approach, I guess. But it was also one of those things like, even though it wasn't my wife's fault that I wasn't transitioning at the time or treating it, it was building resentment just generally.

31:03Like at her, at the world, like they won't accept me and now I have to suffer because of that.

31:10Ryan Holiday: But it's weird how something, how long something can lay inside you. And then as soon as you put a name on it or think about it, it becomes something you have to deal with. Yeah. When you just realize that's what the mind and the body must be doing as some form of self-protection. Right. Well, before it was pursuit of achievement. So it was whatever this thing is, if I just get a degree, if I just go to flight school, if I just have a house and a wife and a dog and all of that thing and a kid. You know, that's the, I guess, productive version of dealing with whatever it is. It's a way of pushing it away.

31:51You need something to pursue in hopes that this will be the thing that fixes whatever this is. And I think on top of that, flight school is kind of like my last big thing to do. And then afterwards, I would just try to be an expert pilot. And so there might have been some timing and correlation to that as well of like, I've done everything else.

32:14Ryan Holiday: Well, you've eliminated all the other things that could possibly be the source of whatever the discontent, confusion. Yes. Yeah. Like I was playing in the church band, you know, my wife had a daughter. So like, Like, you know, I was helping raise her in the home and from five to 18. And, you know, it's just like one of those things like you're like, but there's still something else. And like. But you're busy, so you can't think about it that much. Well, yeah, if you're busy, you won't think about it. Yeah. You just think about the next thing. Yeah. But. And you get locked in a box for a while and you're not busy for a second.

32:47There's nothing else but to think about it.

32:49Ryan Holiday: Yeah. And you can't even, you don't even have the energy to think about something else. Right. Right. Because all of that is gone because you're depleted. Yeah. You're left with what your mind wants to think about. Right. Even against your own will. So. Yeah. Yeah. I mean, hour one, I was singing songs to myself, you know. Yeah. How many hours into it is this? Eight-ish, 12-ish, I don't know. It was probably like three quarters of the way through, I've already guessed. But you know what's weird? Like, you know, like you think you're dreaming like the whole time you're asleep and then actually it's like two seconds, you know, like the dream could be the last like millisecond as you're waking up because it's all in your mind.

33:33Ryan Holiday: And that is the weird thing about those sensory deprivation experiences is just how much it reveals. Like, like I remember I was in a sensory deprivation tank one time and I had this experience that I was like spinning around that I like that I was floating in a circle. And then then they turn the lights on later and I was like, oh, that's physically impossible. Like I couldn't have done that. Like I was obviously just here laying in the exact same position. But when you just lose your bearings and all the things that sort of tied you down to how you thought things had to be and were. And so, yeah, this all could have been in the first 20 minutes.

34:13Ryan Holiday: You don't know, I guess. Right? Yeah. Like, I know other things happen before and after. Yeah. Yeah. But no one was there coaching me in there or anything. Interesting. Yeah. The only interaction was negative if there was interaction with anybody else. Are there other people in different cells near you? How does it even work? You're aware of other people around. Yeah. Sorry, because it's kind of classified. I don't want to give too many details, but yeah. Have you talked to other people who had similar awakenings in there? No. I mean, other people had things, but men, they don't like talking about stuff like that.

34:51They're not going to say that they had epiphanies of all sorts of wild stuff, maybe, if they're really open, but they tend to not be so much. At least military men.

35:04Ryan Holiday: Yeah, I guess. Yeah, that's interesting. But obviously, leading up to the training, people who've been through it, like, oh, enjoy the box. Like, it's a common thing. But everyone I ask, like, hey, like, of course, they say no. like no like i was just really tired of hunger or i thought i saw a ghost you know it's like very like surface level but i wonder if some of them had some other things that they explored but maybe too embarrassed to talk about not necessarily like identity or anything like that but even other like crazy fever dreams or whatever yeah and then how quickly we push those things back down where they belong.

35:43Of course. Or where we think they belong. Yeah.

35:45Ryan Holiday: Right. Yeah. If it's anyone's fault, it's the army's fault. You know, I should get disability for what they did. Well, if they, if they're claiming it makes you unfit to serve and it happened there, I don't think that's that. It's funny that it's, yeah, because of it, I'm unfit to serve, but it's not a medical condition I can claim in the VA for disability. Right. But it's disqualifying for service. Right. So that's kind of a fun one. Yeah, or it's somehow a choice, but it means you're unfixably broken because you made the choice. I mean, we all know that if it was really because of a medical condition, they wouldn't have put animus language in the memo of being inherently inconsistent with an honorable and disciplined and truthful lifestyle, because that's verbiage that was actually in there.

36:29And so if it was truly a medical thing, they would just say it's because it's a medical condition, but they wanted to make it sting a little bit as well. Yeah.

36:39Ryan Holiday: I don't get, I don't get why people care so much. That's always been the weirdest part about it to me. I know why a lot of people tell me they care and it's all the things that the army had controlled for to allow us to keep serving. So like case by case basis, if you're not deployable, you can't serve. Doesn't matter what you have. If, if, you know, you have these complications or whatever it is and it's like, oh, well, the cost. It's like, well, the army spends more on Viagra than they do gender affirming care. So it's like, what's really the problem here? It's like, hey, we're just uncomfortable with you.

37:12Ryan Holiday: Yeah. Yeah. Because it is uncomfortable. I can, it's funny too. Like I find it hilarious, like this life I lead, because it's just, I never thought I'd be leading it. Yeah. You know? And so I can, I come from the conservative of Christian world. Like, so I understand what this looks like and what this seems like to people. And so I just, I just want to build those bridges though. Like, I don't know. I think I can, I can make a difference. Before we get to that. So you become the pilot and then, then the new administration comes in, your status looks like it's going to change, but then there's other adding absurdity on top of absurdity.

37:49Ryan Holiday: Yeah. So I'm worried that I'm going to be kicked out because the election happens and that's what he said he was going to do. But also he said that in his first term and there was an exception clause. So they were grandfathered in anyone who had already transitioned while serving. And that was part of my reasoning under Biden why I went ahead and jumped in and did it because I was like, well, this might be my only opportunity because they might close the door on it later. And so in 2023, that's when I started that process. And so come inauguration time, 2025, January, in the first week or so, the executive order comes out that they're going to ban all trans people from serving and that it's likely going to be a full purge as well, where they're going to kick out anyone who has ever had a history of gender dysphoria or had ever attempted a transition, which I don't know how you define that, but - They put on a wig one time?

38:45Ryan Holiday: Right. Yeah, yeah, right. Yeah, yeah. Who knows, right? Like they painted their nails. Oh crap. Yeah. That's half of California, right? But no. And so like, that was a lot. And in the same timeframe, there was a terrible tragedy over the Potomac near Reagan airport, where a Blackhawk collided with a airliner, killing everyone involved, all 67 people. Wait, that was January of last year? Yeah. And so around the same time, so like I had been asked by someone I worked for, Michael Smirconish, who has a SiriusXM show, he'd asked me because he knew me personally, hey, would you ever want to write kind of like a reflection on being trans in the military as a way to humanize the story?

39:27Because I don't think people understand you're the person that's being kicked out. They think it's these, you know, kind of cartoon characters that, you know, blue hair and like undeployable and just, you know, sucking off the government's teat type people. And I said, you know, like, let me think about it, like, because I knew the risk of being public and being targeted by anti-trans people. Plus, I was still technically serving and I didn't want to risk my service for maybe someone misconstruing that I'm speaking ill about the administration. And I figured, well, this is my chance to actually be brave and be all these army values I've been taught and religious values and speak about it.

40:11And so I wrote this essay and just said, it was basically a love letter to service. Like I want to keep serving and I will serve until they won't have me. Like I didn't speak ill about the administration, just talked about my personal journey and how important service was. And coincidentally, that was published the same day the crash happened. And so somebody found that essay and twisted it to say it was a suicide manifesto and that I was the one who flew the Blackhawk intentionally into the airliner because it was such a non-deviation flying straight. Everyone was like, oh, this must have been intentional.

40:52And then on top of that, there was an unnamed female pilot that the administration had held from releasing for a few extra days. And the president had made a bunch of, well, we know it's DEI. We know DEI was involved. And so between all of that, someone had put together with my essay and pictures of me that I must be this unnamed pilot and I intentionally caused the crash. And I'm another example of being a trans terrorist. And that happened on x or twitter and i didn't even have an account on there and so i wake up to text messages of people asking am i dead or friends asking do you see what they're saying about you online like are you okay and then i received a phone call from the daily mail which i'd never talked to the daily mail

41:41Ryan Holiday: before and there's a british guy there and going i'm surprised you answered you know what's being said about you online yeah and i even though that by nature of you answering the phone right is disproving the rumor that you died in a plane crash. Right. Yeah. Well, no big media outlets were running with it. They were just running with the rumor that was happening, right? Right. And so I Googled myself, which is a weird thing to do as a private individual, and saw all sorts of stuff being said about me. And so seer training, right? Proof of life video. I'm going to put a video out that hopefully I'm going to say it in a way that can't be turned into more propaganda, right?

42:19all this training immediately came to light. And I record this video as clear as day as I can that I'm not involved. And this is terrible that you're doing this. Like it's insulting to the victims of the crash to try to tie me up into some conspiracy theory. And that went viral, the video itself. And then of course I had a wave of direct messages and things about how I'm a plant and I'm taking the fall for someone else. And I was actually supposed to be dead, but I spoke too soon and they didn't have time to kill me and wild stuff. On top of that, death threats, you know, like the fact that like, oh, you are a person that actually exists and you are alive.

42:58Well, we don't like that. Like, you know, very much messages like I can't wait to spit on your grave and, you know, things like that. It's just like it's a lot for still trying to make coffee in the morning, you know, on a Friday morning. So when you've done literally nothing wrong, I did nothing. Yes, I did nothing. And so, you know, the next morning I was on CNN live telling the story. And in between that time, I hid my family. Like we all went to separate locations. I packed bags, I armed all my firearms, I concealed carry. Like my fear was that.

43:30Ryan Holiday: Again, you're having to do all of your training. All my training came to light in the most, like you expect to get shot down and or you expect to be in a war. But here I am at my home in Virginia having all this happen. and my private employer saw everything happening and reached out and said, hey, look, we can hire security for you because we do this all the time when there's like C-suite people that like, you know, I said, that would be great because I'm scared to death that something's gonna happen. Not to me, but to my family or to people who are associated with me. I mean, I had friends that own bars in Amsterdam calling me saying they were seeing it on the news.

44:06Ryan Holiday: Right, it's like a global story. It was a big story. And I think a lot of people, when I tell the story, they're like, oh, but you were alive. So there's nothing there. I'm like, no, you don't understand. Like now I'm a trans Black Hawk pilot that's alive. Yes. Then people didn't know existed. Right. They didn't think that there was a trans Black Hawk pilot in the world. Right. And now I exist and I'm not the only one. And it's just like, and then they found out that over the course of my transition, I was also converting to Judaism, which added to the rumors. Right. Now, now I'm like the DEI wet dream, like trans Jewish, you know, like all these things.

44:41Conspiracy bingo. Yeah. So that was an intense weekend to say the least. And life hasn't been in the same sense.

44:48Ryan Holiday: When I've got to imagine, not just like as a trans person going through life generally, but a trans person trying to not get kicked out of the military. The whole point is that you're just trying to not draw attention to yourself. Exactly. And here the whole world is looking at me. and then the perversion of it is like you're trying to fly under the radar and then they're like why are you shoving this in our faces why can't you just be normal and you're like i am being normal i was just living my life yeah until you put this on me yeah i had many people say like oh you're making trans like your identity it's all about being trans and like no it's just that's the story yeah someone said it was a trans person that has weight to it because elon musk loosened a lot of controls on Twitter after he bought it.

45:34And it became very common that in the first minutes of any tragedy, any shooting, it was a trans person. Because he also has a personal vendetta against the woke mind virus, as he calls it. Because his child, one of his children is trans and he believes that they were corrupted by this woke mind virus. So he has an especially like a sensitivity to trans issues. And so stuff was flying on X, like no big deal. And so there was, it created a, like a very fertile ground for something like this to happen. And for it to go so far because so many other examples had happened and it kind of just created this machine that something happens, tie it to a trans person, get all the clicks, get all the outrage, and then maybe it'll be true.

46:27If not, we'll just delete it. And so when that happened to me, which is one of the reasons why I was hesitant to even publish the essay, I said, okay, well, I'm going to fight back.

46:37Ryan Holiday: Yeah, the instinct when something bad happens to think about what's a minority group I can blame this on, or how can the presumption be that it's a black pilot or a Jewish person or a trans person, is such an insidious and dark form of racism and bigotry that we just kind of accept it as a society is somehow like a normal political talking point, and it's not. It's amazing, isn't it? It's insanely dark. Well, it comes from the idea that what they're doing is they're saying, well, it's not because they're black, it's because these DEI policies put unqualified black or trans people in these positions, and if they had used the normal meritocracy system then we wouldn't be questioning their skill set because they're black.

47:25Right.

47:25Ryan Holiday: Even though by assuming that you're also inserting the person into it, you have no idea who it actually was. Exactly. But by presuming that because it was a woman or it was this race or that race or this orientation or that orientation, that they are, if they exist, one of the unqualified token recipients of the promotion instead of one that earned it. One that earned it. That is the racist. That's what we're talking about. Right. Right. Yeah. It could be that in one specific case that some woefully unqualified person slipped through. Sure. And if that was what the evidence happened to be, then you'd be like, OK, this is why we don't do that.

48:05Ryan Holiday: But like what you're doing is presuming that happened because that person looks like a person who could be that thing, which is racism. It's at all. Just at the end. It's just you could make it as complicated as you want. You're being a bigot. I don't know what to tell you. It's wild because I never got any DEI beneficiary. It's not like I was in flight school passing the same evaluations everyone else was by the same instructors. Because I went through as a guy. I didn't transition. So it's like, what are you talking about? It was no DEI for me. I went through as a straight white male. If anything, that was the advantage.

48:44yes like i had a i had a female stick buddy is what they call when you put in pairs in flight school and they call him your stick buddy because you fly together and you do everything together and i had a female partner stick buddy and she had an instructor tell her to her face women shouldn't be pilots in 2021 in flight school right so where where is the like advantage she's getting when she would get all the hard questions and i would get the softballs whenever they would sit down and do like some like just knowledge, like oral, like back and forth. It's like, oh, tell me about this, tell me about that.

49:19And like, I could just like confidently BS my way through it. And then like, they would just grill her for no reason. It's rare, but it still exists. Like,

49:29Ryan Holiday: especially in aviation. Like that's such an old school, like good old boy circle. And thankfully it's, it's changing and it has changed in a lot of ways, but you know, those 50, 60 year old, 70-year-old instructors, they haven't changed that much. And so they still have their biases that whatever they were taught growing up and it comes out and you see it and you're like, yeah, but I was a straight white male. What was I going to do? Right. How you experienced that as the person's partner then probably lands a little bit differently now. Because I have to imagine she could have had a whole life like that, but not just that instance, right?

50:08Yes. And in my mind, it was just happening there because of that environment. And so you have a whole different appreciation when the eye of Sauron's on you.

50:21Ryan Holiday: Yes, yes. Right? Sure. And so that's just, it's crazy because I still am conditioned as a guy in a lot of ways. So like in business meetings or whatever, people will sometimes try to, I guess, treat me like a lady. And like, I, it, it bounces off. Cause I'm like, I just say it. I'm just like, why are you talking to me like this? Yeah. Like, no, I should get this raise. Like I wasn't conditioned to make myself small in that example. Right. And, and so it's, it's weird living on both sides of it. You know, what's weird to me about the trans thing in the military is it like, it seems like the definition of a don't ask, don't tell situation in that, like, who get like, How does this affect anyone but that person when they go home at night?

51:10Well, they're reviewing women in combat effectiveness now. Right. So it wasn't just trans people and their medical condition. Well, maybe women aren't effective doing these jobs they've been doing for a decade, right? Right. So it's almost like Project 2025 was exactly what they wanted to do.

51:29Ryan Holiday: Which they said they wanted to do. And then people were like, no, no, no, no, no. It's like, oh, all these people very close to the president wrote it. It's like, yeah, but that's not what they're going to do. And it's like they're slowly implementing every piece of it. Yeah. And I don't know. They've kicked out about 6 ,000 or so well-trained trans people that I think are going to make a very interesting resistance to it. I was going to ask you, yeah. So how many trans people do they think are in the armed forces? Between six and ten-ish. They don't know because, believe it or not, the Department of Defense doesn't track it.

52:05Ryan Holiday: Sure. Because it's a note in your medical file. It's not a status that anyone can see anywhere in the system. And so they needed us to out ourselves in order to kick ourselves out. Yes. And the 6 ,000 out of how many people are we talking about? Oh, I don't know. Like, gosh, I don't know what the current. But I mean, it's an incredibly small. Yeah. Yeah. And of course, when I tell people that they said, well, they kicked 6 ,000 out because they wouldn't take the COVID backs. And I said, yeah. And that was stupid, too. Sure. Like, if you didn't like that, why are you OK with this? Oh, because it's not about what it is.

52:41It's about retaliation. It's about punishment. It's about the idea of I didn't like your side, quote unquote. And now my side is doing things that I'm it's like they're glad that there's some bullying happening, like on a meta level. Like, yeah, they want someone who will bully back because they felt like they were bullied. That's my best guess when we're talking about them. Sure. Yeah.

53:04Ryan Holiday: Yeah. No, it is just weird how enormous a political issue it is for something that is. Well, it wins. Yeah. Right now. Yeah. And it wins because of, you know, the things that I get in trouble with when it comes to, like, trans organizations. It's like, it wins because gender-friendly care for children is, you know, very controversial. And then, of course, trans women and women's sports. Yeah. Which, shocker, they do generally have an advantage. Yes. But again, it affects such a minuscule. Right. Right. Amount of people. Right. But that becomes the wedge issue, right? That becomes trans people represent this very small edge case of a thing that is not great.

53:49And I mean, even like on ships, like women and children first, right? That's who we protect. And so what is the trans issue? It's mostly women and children, right? It's, we don't want mutilation of kids. And on top of that, we don't want men coming in and stealing trophies from our women. Yeah. And so it falls, I think, on more of that. More core consciousness of like being an American is like protecting women and children. I don't know.

54:19Ryan Holiday: I don't know. I think it's more like this thing makes me uncomfortable and I can't just say this thing makes me uncomfortable. So what can I where can I find one or two edge cases where it makes a lot of people uncomfortable or there actually is some legal or, you know, health thing to be concerned about. So then I can say, oh, no, no, it's really just this. And so it's it makes it makes an illegitimate thing seem legitimate. Does that make sense? Like, I think that's more what it is. I think when you're talking like political operatives, yes. But when you talk to people who get the result of all that messaging, they don't think that way.

54:59They're thinking this is an issue.

55:01Ryan Holiday: Yeah. Because they're being told it is. And because the biggest issue is that most people don't know a trans person. Right. Right. And so when people ask me, like, oh, why are you doing all these engagements, speaking and comedy and like being so public after everything? It's like, well, because it's like no one else is telling the story. Every time you look at your phone, there's another chaotic headline. You almost feel like you have to be glued to your screen to keep up. But saving for your future doesn't have to be this hard because Wealthfront helps you tune out the noise and earn more with a high yield cash account and sophisticated, easy to use investing products.

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58:15Ryan Holiday: You do, and you don't know it, which is how it not just should be, but which is the point, which is it's somebody else's thing. It's somebody else's life. It's what somebody else has beneath their clothes or deals with their doctor. and that's all that it is, which is to say no concern of yours, right? Like, and so I think there's that. And then, yes, there is something I do think really important about meeting and knowing some representation is so important because then you go, oh, okay. Again, it's nothing. Like it's, again, it's normal. Like all things are normal. Exactly. Yeah, and I keep going into these traditionally red circles for that reason, right?

59:03Like I, as a soldier, you run towards the front. You know, you don't, I don't want to be in the, the liberal circles, the glad, you know, rooms because you already agree with me. Yes. Right. I mean, my parents voted for Trump each time. And it's like, I want to win them over. And maybe that's like a weird piece of this. It's like, you're trying to win back your family.

59:26Ryan Holiday: Yeah. Yeah. In some way. How's that going? It's going great everywhere except them. You know, I meet people all the time. The exact inverse of how it should be. It's very much like, I never realized that this is what this is. You know, that you're a trans person. Like, you're not anything like the things I thought. Right. Right? I mean, other than like a few other prominent trans people, like, there's still not a whole lot of examples. And I don't think we should be given spotlight just because we're trans. And that's one of the things after the crash rumor is like, I don't want to be known for something that I didn't do.

1:00:02Right. Right? And so I'm on this journey of figuring out how to become known for something I did do. And not waste something that, while it was a tragedy in the sense of the crash itself, but also a tragedy in how it turned my life upside down. But also making lemonade out of lemons.

1:00:23Ryan Holiday: When my wife and I moved out here to the country, we bought this ranch. And we were both from California and the suburbs, had zero experience. Our neighbors were these two women, and one of them was trans, and her name was Vivian. She's amazing. She's the one that showed us how to use a tractor. She's the one that showed us how to fix things. Actually, we were so helpless that afterwards she started a charity that helps, like, basically city slickers do what we did. Oh, that's amazing. But, like, she showed me how to do all this stuff that, by the way, my dad never showed me how to do. Right. She worked on oil rigs.

1:00:59Ryan Holiday: She was a vet. also she lives in Colorado now. She was running for, I think, state Senate there. But like, we would not have survived like literally and figuratively without this person. And I think about it all the time because like, I don't know if we ever talked about it, which is kind of the point. Like, you're just like, you know, maybe you can tell, maybe you can't. Maybe somebody told me, I don't remember how, like, I don't remember how it came up. But then you're just like, that's a fact about this person amongst many other facts. And then you choose whether that's going to be the thing that you let define them or you choose whether that's a significant fact to you or not.

1:01:40Ryan Holiday: And to me, the way more significant facts, not that this is insignificant or significant, it's just like the things that matter to me about this person is all the things that they did and the kindness that they showed us and the friendship that they showed us and that they were fun to hang out with. So you have those experiences. And so it was sad one day to wake up when she was running for office. She's on the front page of libs of TikTok, you know that account? Oh, yeah. Yeah, they posted that rumor too. Yeah. And so what I think is really important is not just meet this person and you become friends with them and then you go.

1:02:15Ryan Holiday: then when someone decides to treat them shitty, there's a human face on that too. You're like, you're, you, a person whose only job is posting random bullshit videos and rumors on the internet had decided to take this person who's been incredible to me and to make them into some sort of predatory monster or some sort of degenerate. It's like, no, that's not going to work for me. I think that's what needs to happen more. Sure. Well, it's like I tell most people, like I'm all these things like Blackhawk pilot, now a comedian, like used to be a level two CrossFit trainer, like all these things. I just happen to be trans.

1:02:56Right. Like, and that's how I wanted to be. Like when I came out to my unit, it was kind of like, oh, cool. Like it was a non-event. Sure. Like everyone I came out to, I mean, other than my parents, of course it was an event. Like my wife, of course, it was an event, but most of my friends became closer. Like people I worked with in my private job, I came out and they're like, okay, like no big deal. Because why would it be a big deal?

1:03:19Ryan Holiday: The only people that made a big deal about it was current administration who made it a winning campaign issue. And of course, everyone who likes to feed off of that and like lives at TikTok who just makes a living, you know, getting retweeted by Elon because he owns the platform. So it's just, I don't know. And that's a tragic in itself because Elon's got so much to offer to the world. You know, it's just like, God. Yeah. Who has the mind virus? Yeah. It's interesting because, yeah, like we're all susceptible to the toxicity and the corruption that is being popular. Yeah, and you would think, though, when something like that happens to one of your children, there's very few things that your children should do where your impulse is like anger and judgment, and especially when this is happening in public.

1:04:23Well, they don't reflect the parent. They're their own person, especially when they're an adult. But also, my parents, I applaud them because they didn't react that way. They still tell me they love me. They don't understand. They think I'm inherently on the wrong path based on their belief in Christianity. And that's, I can respect that because I understand where it's coming from. It's not coming from hate or anger, like towards me personally. They want the best for me. They just think the best for me is this other thing, but they still love me. And I just, I don't understand why I have a daughter.

1:05:04Like, even if she like, you know, like whatever I can think of that she could do, I can't imagine reacting that way. Yes. You know, it has to be ego, right? It has to be some form of ego.

1:05:16Ryan Holiday: Yeah. It's like, you're like, I don't want to lose my child. So I'm going to push them away really, really hard. It doesn't make any sense. But it happens in history, right? So like, what is that instinct? Like, how is love not the first instinct in this world? Like, I just don't understand it. With so many people claiming religion, especially Christianity or whatever, like the first principle of all of this is love. And love shouldn't make you angry. Yes. Love, understanding, curiosity, acceptance. It also just seems like a much better way to go through life. Like even if it was a choice, even if it was harmful, even if like people do lots of crazy shit.

1:06:02Ryan Holiday: Exactly. You know what I mean? People smoke cigarettes, people do all sorts of things that may or might not be great for them or the people around them. Yes. Right. And it's weird that some of those things are just so much bigger to them than others. Right. And how we hold those things in society even is like we hold the trans issue so much higher than what is killing children. And we're worried about this very small subset of children that might have got some care that was risky or dangerous or maybe not appropriate even for them. but yet the number one killer of children i think was firearms or something like that many many many like yeah like guns yes which you could actually do something about right now and which which you can't restrict at all yes even in a lot of circles so it's just strange to me like the things that we go after and it's you know you always fear what you don't understand right like that's part of it too well i think that the child one is is another one too it's like one of the things i've learned having kids who are, I guess you'd say neurodivergent is like, you have a lot of opinions about things before you have kids.

1:07:08Ryan Holiday: And then before you have your kind of kid, like whatever your kid is, right? Like we all have opinions about like, why don't parents just do this? Or, you know, the solution to that is this or, and then what I think happens is God gives you something that challenges that very assumption. And in that moment, you realize you had no idea what the fuck you were talking about, right? And if it was only so easy or as simple as you thought it was. And if you've met any parents who have children who have gender dysphoria or are curious or whatever, what you realize is like, they, like you, are totally overwhelmed, are trying to do the absolute best thing that they can for their kid.

1:07:49Ryan Holiday: And then they're having a hard time. Are there some parents, as there are in all facets of life, who are doing totally fucked up things, you know, parents who are using their kids to do this or that, sure. But the vast, vast, vast majority are trying to do the best thing they can for their family and are getting the best advice they can and are not sure. Like, I remember my wife and I were talking to someone about like, you know, should we send our kids at this kind of school or at this kind of school? And he said, you know, I haven't met any parent who's like, we figured it out. You know, that we are sending our kid to that perfect school.

1:08:29Ryan Holiday: He's like, every parent is questioning their choices. And when you realize that, you go, I just honestly, I don't have any time or authority to think about what you're doing at your house or what those parents are doing in that state. Because like, I'm underwater over here. Yeah. If you're really doing the work. Yeah. Yeah. Then it's difficult and it's a journey. It's not a one and done anything. You can do everything right and it's still end up wrong, you know, or different. The greatest contradiction to the, when it comes to gender dysphoria for youth is in the UK, they banned it after having it.

1:09:11And then they said, actually, we're going to do a study now. And the people who were against it because there wasn't conclusive studies are also against the study. Sure. Because now you're experimenting on kids again. And it's like, well, we're trying to get the data that you say doesn't exist to justify it. And now you're saying we can't even do that. So, yeah, I don't know. People just, they got too much time on their hands. There's other stuff to do.

1:09:36Ryan Holiday: A lot of people spend a lot of time thinking about other people's genitals. And that's, I think, our main problem. They're chronically online, right? It's like that is, the woke mind virus is that. It's being chronically online. And, you know, it's very freeing to just not hold an opinion about stuff. Yes. right like you know this is actually one of the core ideas of stoicism i was gonna say this is from marcus really's right like there's power in not having an opinion well no he says you have the power to have no opinion yes right yeah and and there's power in that yes totally and and a lot of us are like no no no i gotta make up an opinion about a thing that i just heard about you know why right it's because when you scroll each thing you see is asking you for your opinion yes and either an overt or subvert way, it's asking you to form an opinion because you read it and you're like, what do I think about this?

1:10:27Yes. Even you're asking yourself your opinion on it. And it's exhausting. Right. By the time you're scrolling for an hour, you've had to decide and come up with your thoughts on so many things that doesn't pay your bills, doesn't feed you, doesn't help your kid. Like you're just wearing yourself out.

1:10:48Ryan Holiday: There are things that for the most part, you wouldn't have known existed if you were not. And then also we're specifically and algorithmically filtered for you to elicit strong, positive or negative opinions. Right. So on top of just that, that mechanism, now it's also plotting against you. Yes. Yes. To basically make you an, a judgmental sort of like intolerant asshole. Yeah. And then you put it down and you walk outside and your kid's doing something you don't like and your reaction is completely different. Yeah, sure. Because you're amped up, you're something, right? And it's just nuts to me.

1:11:31And people don't, they don't understand like you're literally playing with something toxic every day when you're scrolling and doing these things.

1:11:40Ryan Holiday: Well, it's toxic for you. But then also, I think what your experience is a reminder of is that it also has toxic effects for the other people that you've turned into a video game. Right. But it also changes how you interact with people in real life. Yeah. Right. And they're like, oh, it's just online. It's not real life. But it's so much is. Right. And it's tough because like I think in productivity, like they talk about like decision fatigue and you have to make so many decisions. And the best way to like kind of orient your life in the way you want it is to, is to have many things already decided, like whether that's what you wear or what you're going to eat.

1:12:16If you don't have a lot of options and you narrow it, then it's not a decision you have to make. So you get to save that energy. And so when you, when you crack open social media, you're just, you're, you're spending all of that. But you're spending all of that on passing the time. So when it comes to when you need to have those resources, you're spent, whether it's your child or your parent or a job or whatever it is you're doing or you're driving. And now all of a sudden you're angry at everybody. And it's like, I've already wore myself out for the day and I hadn't got out of bed yet. Because you wake up and you just start scrolling, right?

1:12:51Sure. So it's wild. I'm a big fan of like Cal Newport, like digital minimalism and like a lot of his books, but in general, like stuff like that. And of course, Atomic Habits was huge to me and, and understanding that. And just, I try to example, live that example because I don't know any other way to show people like this is really healthy and a good way to kind of, not that I get it perfect, but, you know, you see people that are just chronically online. And like, once again, I lead with love. It's like, I feel for them because I've been that person before. I know what it's like and I know how easy it is.

1:13:29And, you know, people are capable of so much great things and beautiful things. And, you know, most of us are just, you know, getting an IV drip of toxicity.

1:13:42Ryan Holiday: On a lighter note, what drew you to want to do comedy? Seems about as opposite as being a helicopter door gunner as there is. I wanted to change people's minds. So maybe not as light as you think. I was telling my story about the crash and the trans military ban so many times because I wanted to speak out that it was becoming kind of like a dry for myself. and I said well how can I like change this up or whatever and a huge fan of comedy like you know many many years just growing up and going to see comedians just love everything about stand-up comedy and I decided to try to put some jokes in one of my talks and I got I got laughs and it was addicting I was like oh this is this is exciting I got a whole room of liberals to cheer when I said we need to buy more guns like we need more liberals with guns.

1:14:38And when they all were like, applausing, I was like, interesting. And then on top of that, the power that comedians have been given with podcasting in the current political landscape. And so I said, well, what's the best way to do it? Like, write my five minutes. And where am I going to go tell my jokes? Austin is the home of Joe Rogan's new comedy club, because I listened to Rogan for a decade, like a big fan. And I know that he has this show through Tony Hinchcliffe called Kill Tony. And I was like, well, I can go down to Austin and sign up and maybe I'll get picked. And so I, for four weeks, I went to open mics, trying to learn how to do it.

1:15:18And then flew down to Austin in June and signed up and got picked the first time I signed up out of a random bucket of, you know, 300 people and told my story in a funny way to a sold out room in Austin, Texas. and how terrifying was that well i'd already been accused of murder so it's like yeah um you know it's it's tough right like you don't know what to expect and you hear all the things about how far right everybody is and they're not really you know it's like they're very friendly and kind but you know i knew everyone would be waiting to jump on any sign of being a woke snowflake right and so it was thrilling.

1:16:02I was hooked. I was like, oh, I think I want to do this longer term. And so I've been spending a lot of time in Austin, just building my material and producing a show soon and like going and getting spots at different clubs and, you know, infiltrating the comedy scene. You know, I called it jokingly before I came down the first time. I was like, I'm going to call this like Operation Conservative Psy-Op. You know, I'm going to go down there. I'm going to get into this world and it's going to be considered like admirable because I didn't just come in and like browbeat them. I came in, learned Rogan's craft, did it on his stage.

1:16:38And maybe that will be, even though it's very unorthodox, maybe that's what people need to see of a trans person to help shift, you know, change minds.

1:16:50Ryan Holiday: Yeah. There is something, it is interesting to watch that clip because people spent a lot of time making fun of something and then sort of forced to interact with it as something real and not just... Well, especially in comedy in these circles here because there's not many trans comedians. There's just a few of us. And a lot of sets, if not every set, has a jab at trans people, funny or not. And some of them are great. I love trans jokes. I tell them myself. and I think anyone can tell a joke if it's funny like I'm not into that but it's very low effort a lot of them because it's easy when it's a room that you assume there aren't any trans people in right it'd be the equivalent of making like the most low effort black joke right yeah like it's kind of hacky and what I learned is going to these sold out shows sitting in the front row and making myself known to them that it forces them to to elevate like it forces them to write better trans jokes yeah because now it's not just this thing that you can kind of like this punching bag in the corner now it's a person in the front row who paid to see you right and oh now it's a person who's up next right like or now it's the person who you're following after they open the show for you yeah and so it does give a whole new world and oh by the way it's this person that like rolls with the punches and like kind of has thick skin and will make the first trans joke in a room and isn't going to like, you know, come down with all these like liberal woke ideas or tell you you're wrong.

1:18:26Right. I'm just going to lead by example.

1:18:29Ryan Holiday: Right. And so that's, it's been very rewarding to, to be operating like that in this world. Well, that's very exciting. Yeah. Going up on stage is a scary thing, but it's exhilarating yeah yeah probably not unlike flying yeah yeah i mean it only feels like you're gonna die you're not literally gonna die but there is that feeling well and like part of my set is like yeah i was flying blackhawks until last summer and now i'm here telling dick jokes yeah because if you don't let us do what we're cut out to do like what are we supposed to do you know and it goes back to like the tropes of like trans people being sex workers it's like well, give them an opportunity to do something else, right?

1:19:08Like if you're restricting them from military service after, in my case, 16 years, deployments, medals, it's just a misallocation of resources. You know, like I cost a million dollars to train.

1:19:23Ryan Holiday: Probably more than that. Well, yeah, but definitely a million dollars for flight training. I thought Doge was all about saving money. You know, it's like there's so many contradictions to it. And it's like, I think me choosing to tell jokes on stage has been the most effective form of advocacy because it's not pushing advocacy first. It's, let me tell you some jokes. Let me throw some things out there. And that will soften you to be open to considering things differently. Right? I'm not telling you how to think, but it's been so rewarding. I get so many messages from people like, especially after Kill Tony, like you're the kind of representation we need or like I never thought about it this way or I can't believe you're not getting your retirement from the military.

1:20:08Like I can't believe they're screwing you. I didn't realize this would happen. And these are a lot of people that voted for Trump. Yeah. You know, and so it's in that sense, it's rewarding. And as long as people will let me keep telling my story, I'll keep telling it, you know. And so I just actually started writing a memoir, which is another, I love learning.

1:20:29Ryan Holiday: Yeah. So this is a whole nother process. Seems like you like challenges. Yeah. Like being way in over your head and doing something you don't know how to do. Well, the obstacle's the way, right? Yeah. Yeah. Well, I got some books I'll give you that'll help. You want to go check them out? Yeah, I would love to. All right, let's do it.

1:20:54Thank you.