With Tim recently turning fifty, he shares the effect it’s had on his mindset and personal growth. The boys then take a deep dive into nostalgia and reminisce on some of their past memories while looking ahead to the future.
The Teaching Transformations Podcast. Join Tim Desmond Ryan Wooley as they help teachers in their late forties or fifties to design a post-academic life.
Seize the Day!
Welcome to Teaching Transformations, Designing Your Post-Career Life with Tim Desmond and Ryan Wooley.
Man, I know someone who recently turned fifty.
I feel bad for them.
That’s old. How do you deal with birthdays?
I ignore them. I really don’t think much about it.
What about your family? Do you guys have any kind of rituals or routines or anything for birthdays?
So, siblings, we acknowledge each other’s birthdays. I have two older sisters, and usually we send a card and/or a text kind of thing. My parents obviously will reach out. I think we may have just finally agreed to give up on giving gifts for birthdays, so yeah, not a big deal. In Christina’s family, they tend to do more. They’ll bring people together, but more for the children.
Yeah. What about between you and Christina? Do you guys do anything?
I’m laughing because we’re the same way.
Like, yeah, I’m surprised if we remember each other’s birthdays.
That’s what Google Calendar alerts are for. Yeah, Joy and I are the same way, like anniversaries, birthdays, we’re terrible about that. I’ll be having a conversation with someone and they’re like, my wife and I are going to go out for a birthday and then dinner and a movie. I’m like, what’s that?
I know. Yeah.
Why do you think that is?
You mean for us?
Yeah. I wonder why for some people it’s kind of a big deal, and I’m not talking about children, by the way, I’m talking about like full grown adults, middle aged people still going out to dinner for their birthday.
There was a guy that used to work in my department that took his birthday off every year.
To do what?
To go day drink, I think. I don’t know.
Okay, I can respect that. I just imagine some lonely guy sitting in his apartment hovering over a cake with a candle all by himself.
Yeah, I don’t know. I don’t judge. I mean, I think we have to look for reasons to celebrate whatever there is to celebrate about life, and I guess for some people, that’s when they do it.
Yeah, I’m with you. Joy and I need to do more of that. We should do more of it. I mean, it’s kind of related to the topic today. I was joking a little bit about knowing somebody who turned fifty recently, and it was me. I really hadn’t thought about doing an episode on turning fifty until it happened to me, and then I also saw a New York Times article that got my attention. I wanted to kind of set the stage here and talk a little bit about what this article said, and then bring it to more personal level and talk about what that feels like. Whether it’s fifty or not, I feel like there’s a moment in middle age, in the forties or fifties, where you feel shift. You feel a change. It could be just me, and I think that’s part of the reason why I want to explore this with you. I want to get into that, but before that, I saw an article on New York Times, we’ll link to it. It’s called Generation X: Your AARP Card Awaits. Yeah, that hurts, right? This is by Alex Williams. The subtitle is, The Advocacy Group for the Over Fifty Set Welcomes a Mercurial Generation that Never Wanted to Grow Up in the First Place. So a few of the highlights, AARP’s market research, no surprise, found that members of Gen X tend to be more individualistic. They are not joiners and card carriers which would be a problem for an organization that issues a card. They askew mass market blindness, and they are all too aware that the future is uncertain. Yep, spot on. Good market research there AARP. One person they interviewed, Miss Shipley, said that Gen X’s life experiences have shaken their confidence which puts added pressure on what already feels like a pressure filled life. They suffered the Great Recession and the COVID-19 recession during their prime earning and savings years, so I thought this was kind of interesting. This article came out just prior to the ad spot that the AARP ran during the Academy Awards, I believe it was. I’ll link to that, too, there’s a YouTube clip of it. It’s some douchey fifty year old skateboarding, so yeah, that’s the context. It was odd. As we talked to the top, we don’t make much of birthdays, and people ask me how old I am, I always have to do the math. I have to be like, okay, ’71, what year is it? But this one was a little bit different. You were part of a wonderful little birthday video that my wife put together where she asked a lot of my friends and family members to wish me happy birthday, and that was nice. I watched that, and my family was very loving, and it was great, but the whole thing just felt odd to me. I think one of the reasons for that is that I still have this rebellious college student mental framework, like that’s how I see myself, and I’m not anywhere near that anymore. It’s just a big bunch of stuff I’m dumping at your feet, and I know that you’re not fifty yet, but are you starting to have any of these thoughts? Are these coming on your radar at all?
Yeah, they definitely are. I think I’m feeling it on two fronts. I’m feeling time’s wing and chariot, as Andrew Marvell might say. I feel that on my heels for sure, and I think that’s affecting me more than anything. I’m looking at my life, and I’m saying it’s finite. I mean, I’ve always known it’s finite, but as you get older, you start counting the years, and you’re like, if I’m lucky, you know, I have a couple, two, three more decades, right? You start thinking about, what can I accomplish in that time? I’m feeling that a lot, and that has me scrutinizing everything I’m doing, like, am I wasting time on things? I know we’ve talked about car and house repairs, and this week, I got sucked into a car repair. I really, really debated before I got into it about whether I was going to do it because it’s quicksand right? I know I’m going to get sucked into it, and I’m going to regret it after, but I still went ahead and did it. I thought I could do it quicker, and of course I ran into problems. Several hours later, I’m like, man, I wish I could have that several hours back, so I’m starting to be more judicious about what I’m doing with time. The other way I’m feeling is I’m not getting as much exercise as I want, but when I am, the recovery time is brutal. I mean, when my son gets pitching lessons, I catch for him sometimes so that the person giving the lesson can watch more closely there. There is mechanics. So, I caught for like an hour long lesson, and then I couldn’t walk for four days.
Being hunched over?
Yes, and then I did it again, and the next time I did, it was much better. It’s just that that wouldn’t have fazed me a bit even just a few years ago, so I’m not liking that at all, but outside of that, I just don’t want to acknowledge it. I feel like the more you acknowledge it, the more you’re sort of caving into what age might be, so that’s one of the reasons why I just don’t feel like I want to pay too much attention to my birthdays. It’s hard to ignore the fifty, I mean, people do make a big deal about it. Even working on that video, I was like, Tim is probably going to have mixed feelings about this.
Yeah, yeah. This is gonna seem completely random, but it’s not. I want you to go meta for me on your memory for a second. When I say 9/11, how do you reflect on 9/11?
I instantly go back to that day. I remember the entire day, and it was an inflection point in my life and in the world. I mean, so many things fell in line behind that event, the war in Iraq, you know, just foreign policy changes and all kinds of stuff that came as a result, our relationship with the Muslim world. Just on a personal level, that day, I was scheduled to go on a trip with some friends, and we were supposed to fly out that morning. I got up and was packing my bags, and my friend, John, calls me and says, hey, did you see what’s happening? And I had no idea, so I turned on the TV. This was before the second plane hit, so I think, even at the beginning, it was like, okay, this just looks like an event. Then the second plane hit, and they were saying this was a terrorist attack, and then, obviously, the day unfolded from there. I remember walking outside, looking up the sky sometime after following the news for several hours. I just needed to get outside, and the sky was crystal clear. There were no plane jet streams anywhere. There are a lot of things about that day that I just like burned in my memory, so that’s an easy one to recall.
Yeah, and it’s a bit skewed because it was such a tremendously impactful event, but as far as your personal timeline goes, does that feel like that was a really long time ago? Does that feel like, wow, that was just yesterday? How does it fit on your personal perspective of time?
It feels like it was a long time ago even though I could remember it very clearly, but there are lots of things that I struggle to remember. I struggle to remember things from high school. I remember teachers faces and everything, but I feel some of those memories slipping away. Does 9/11 feel more recent to you?
Yeah, yeah. That’s kind of why I asked that because for me, I had some of the same very personal experiences. I can still see things, I can still feel things from that moment. I was on a bus with forty sixth graders going to whitewater raft the New River Gorge, and we pulled into a shopping mall in Kentucky because we heard there was something going on, but you know, there weren’t smartphones. Someone from the school called and said, there’s been an accident with a plane. We were half an hour from our scheduled stop, and we walk in to the food court, and there on the jumbotron is the CNN footage. I am standing there right now as I’m mentioning it, and the reason I brought that up is because that’s twenty years ago this year. My dad passed away at age seventy. For me, that’s twenty years from right now. Now, I don’t plan on dying at seventy. I think that’s still kind of young, but who knows, right? The contextual piece I’m trying to put together is for me, twenty years is really nothing, and that’s kind of what fifty is doing in my head. I don’t even know what to say about it. Twenty years ago was absolutely nothing, but yet, in twenty years, I’ll be the age my dad was when he passed, so I don’t even know what to do with that. It’s just kind of tangled up in my head.
Yeah. Well, just throwing out the word decades like I did a few minutes ago, talking about decades like they’re years. I think some of that is because when I look back over the past couple of decades, they went fast. It doesn’t seem like twenty years, and I know that just keeps building steam as you get older, you know, that time does feel like it’s moving faster even though it isn’t. It makes me wonder if people get counseling for this or anything because it could take over and mess with you a little bit.
In a way, we’re such modern humans that like we’re dealing intellectually with things that our paleo ancestors never had to, but we still have the same brain, and I think that that might be at the root of it, but I don’t. I don’t want to spend the whole episode on 9/11 or my dead dad, but I want to talk more about like, what kind of wisdom have we gleaned? Or what have we learned over those past fifty or forty plus years that we can really use moving forward? Because that’s the whole point of this Teaching Transformation thing, like, where are we going? What do we want to do? I was thinking about what I can mine from both the far past and the near past that might help me think about what I want to do with the future, so I thought these might be kind of a fun thing I’ve learned, a conversation piece that we could kick around a little bit more, you can bounce it back and forth. I’ll tell you the first one that comes to mind. This might be counterintuitive when you think about getting older and being more wise is that the older I get, the more I know how much I don’t know. I just feel like there’s so much information, so many parts of the world that I don’t understand and will never understand no matter how many books I read or podcasts I listen to. The less confident I am in what I know, the older I get, and I don’t think it’s supposed to be that way.
No, I actually think that is the wisdom that comes from aging is you become more humble, you know, you recognize your own limits, you recognize that there are a lot of smart people out there. There are a lot of people who become very expert at a lot of different things, and when you reach a certain age, you realize, okay, I can’t be an expert at a thousand things, I can be expert at a couple, so you start to nod to that. I think that’s wisdom, that humbleness and also recognizing that it’s common for all of us. That’s the other thing, like none of us have some secret way of getting out of it. We’re all gonna keep getting older, and we’re all gonna eventually die and knowing that we can’t escape that, I think some humbleness in sort of just acknowledging that.
That’s a good point. I have some millennial and Gen Z friends, and their level of conviction is so strong on certain things, and part of me wonders if that’s just a maturation thing. I look back at myself, and there were things in my thirties I felt really strongly about, and now I’m like, I’m not so sure. It’s not passing judgment, and they’re not doing anything wrong, but even around things we’ve talked about, outrage, culture, and cancel culture. I think there’s some inexperience built into that. It’s this idea that like it’s either this or we’re rallying against you, you’re either with us or you’re not. I don’t know, that feels like a very immature perspective to take the older I get. I find myself in conversations even with very polarizing political and religious overtones gone. It’s just the lines seem a whole lot blurred the older I get.
The more experiences you have, the more you recognize nuance, and the more you can see in between the lines, and the more you can see the gray versus the black and white. That makes a lot of sense to me, and I think that’s healthy. I think it’s healthy to let yourself grow in that way and not be so quick to judge.
Yeah. What about you? Do you have something you feel like you’re better at now or something you’ve learned that maybe you didn’t know ten or fifteen years ago?
I think I’m better at seeing connections between things, seeing the relationship between different events and what those mean. One of my buddies back from high school, he and I were really good friends for a long time. He and his brother used to use this term, querare, I think it was, and it translates to the interconnectedness of all things.
And the older I get, the more I can see that you can see cause and effect. Even just on really practical matters. I mean, we just got news this week that my son’s swim coach basically had a falling out with the administration, so they’ve parted ways. It’s this really practical thing, but looking at all those relationships and being able to sort of predict who is going to react in what way and what effect it would have on an overall mentality of a team and a culture and all that kind of stuff, I guess I feel better equipped to recognize those things and be ready for them, and in some ways, maybe help build bridges and smooth it out almost as it’s happening if that makes sense.
Yeah. I have a few that might be more specific to my own business right now, but I think you’ll be able to relate to these. I’m finding it’s harder for me to get into the creative flow than it was in the past, and it’s because the older I get, my analytical brain is starting to overpower my creative one. I don’t know exactly why this is happening or if it’s my perception versus reality, but I kind of feel like when you’re in your early twenties your late teens, no one ever questions your creative pursuits. Oh, you’re in a band, great, or you’re a painter, oh, that’s awesome, or you’re gonna move to the village and write poetry, awesome. There’s sort of this cultural acceptance of people exploring their creativity in their early twenties. You turn fifty, can you tell someone I’m going to move to the village to write poetry? Don’t you feel like there’s a judgment in that? I wonder if my brain is really saying, well, creativity isn’t as important as it was when you were younger or if I’m sort of channeling those cultural perceptions and saying, yes, that’s not what a responsible fifty year old does, a responsible fifty year old isn’t out at band practice on Thursday night. Do you have any of those perceptions or ideas?
Oh, definitely. I’ve really felt that. It’s funny you mentioned the band practice thing because something that’s really, really important to me is music, and I love to play music. I play guitar. I’d love to learn piano, I’d love to learn drums. I have both of those in my house. I don’t have a lot of time for that, and I haven’t for a while. I’ve put my family first and happily, so I’ve been a happy father and hands on father this week. Every other week, we’ll have probably ten swim practices, two or three baseball practices, three or four baseball games. That’s just part of it, I’m leaving a bunch of stuff out. When I’m getting home at 8:30 or 9:00 some nights and sometimes still figuring out dinner, I don’t have a lot of juice left in the tank to pick up my guitar and learn a new song, you know? It just doesn’t happen, and for me, I know that’s there. I know I want to get back to it as soon as I really can give it time again, but before I really have significant time, it’s still going to be a few more years, and I’m going to be over fifty, and I do feel self conscious about it. I feel like, okay, I don’t think I’m going to play out at coffee house. Although, I’ve been out and seen people of this age play out, so I guess I wouldn’t rule it out either, but, yeah, I struggle with it. I do think some of it is thinking about how people perceive me, like dude, aren’t you too old for that? Give it up.
Right, right. Well, what do you expect to do? You’re fifty, what are you gonna do with that?
Yeah. I just watched a documentary recently with the guy from Crosby, I’m blanking on his first name.
Okay. I don’t know how old he is now, but he’s putting out albums, and he’s touring. He has said he feels more creative than he ever was, and I think he’s pretty far into his seventies.
He’s definitely a boomer, no doubt.
Yeah. So anyways, I think we can make too much of that and let it influence us too much. I guess I hope to try to ignore some of those feelings and just enjoy what I enjoy. Okay, so maybe people will think it’s weird that I have gray hair and I’m playing acoustic guitar and singing to people, but it’s just the way it’s going to be.
An interesting observation you made about Crosby, because one of the other things I’ve come to realize is that I can never retire. Not the way my parents viewed it, like not in the traditional sense, and I think that’s another reason why we’re here is like I can’t see myself not working on something that I’m passionate about in a creative way. If you go back to the boomer idea of retirement or what my parents or my in-laws do, they’re retired, and it’s just basically they do crossword puzzles, they watch TV, they visit the family, and that’s what they want. That’s great for them, but I look at that, and I’m like, I’d go batshit crazy in no time. I can’t see myself ever retiring which means there are going to be physical limitations. I’m not going to retire and then enter strongman competitions, you know, I’m not gonna, I’m not going to retire and then become a mountain climber. So, what am I going to do? I keep coming back to these creative pursuits. David Crosby is in the seventies, and he’s making music. I could make music, I could write, I could create art as long as I’m alive, like they’re there. I mean, there are some physical limitations to that, but not really, you know. I think that’s something else I’m coming to the realization of is like for a long time, I thought of fifty-nine and a half when I can draw down on my accounts, or sixty-five or sixty-seven I saw as the end goal, like the target. Now I’m starting to think, what am I going to be doing differently than in theory what I’m doing now? That’s a big shift, and I don’t know how many folks our age have made that shift yet. I wonder how many people are still just looking at the financial statements and the social security updates and thinking, yeah, I just need to get to there, but then what?
I don’t want to gloss over the physical piece. I do think it’s important to be physically active and to maintain that, and yeah, that might need to change some, you know, maybe instead of running a marathon, you’re just running a 5k or whatever. There are sports that play better with age. Golf is one obviously that comes to mind, tennis, maybe football, probably not so much. I do think some of the limitations we put on ourselves are in our heads a little bit. I don’t know if I mentioned this before, but I remember hearing Mark Cuban say that he learned to dunk a basketball when he was thirty-eight, and he’s a billionaire. He could afford to just spend a lot of time focusing on that task and figuring out how to do it, but the bottom line is a lot of people would assume that you hit that age, and it’s just impossible, and what I love about him doing that and about people who do stuff like that is they challenge that mentality. They’re basically saying, I know most people assume I probably can’t do this, and I’m gonna prove them wrong, and that takes time. I guess it’s my long winded way of saying I do think a lot of this is in our heads, and I want to work hard to not let it affect me even though I know it will. I think that you and I should commit to learning to dunk in our fifties.
Well, I’m sure Mark Cuban’s listening. Maybe he can help us make that happen. I want to ask you about something else that’s in our heads since you mentioned it. What’s your relationship to nostalgia?
I’m a pretty sentimental person about things. I’ve always been nostalgic about things, although I will say probably less so than I used to be, so maybe that is kind of fading as I’ve gotten older. It plays a role in junk that I keep around. I mean, there’s stuff that I have in my attic, in my basement, that I know my wife, it drives her crazy. A few years back, she was talking about the spelling bee trophy that I kept around from like six or seventh grade or whatever that was. I had stuff like that that I kept around, and I know I still do. I’m not sure why I have that. I had this experience, my grandmother, when she passed away, I don’t know, must be going on ten years now, she was a borderline, maybe not even borderline, she was a hoarder. She had lots and lots of stuff in her house, in her garage, and when she passed away, my grandfather was still living. We had this monumental task of cleaning out this house that was just full of stuff like magazines from the 60s that she kept. I think that experience of going through that stuff and throwing it out, there’s so much you couldn’t even really think about, you just wanted this to be over with, so that experience really affected me and made me realize I don’t want to do that to anybody else. Something I’m going to work on over the next ten years or so is trying to slowly go through things and let go of some of that stuff that I shouldn’t really be holding on to.
It’s so interesting you mentioned that. I think you’re right, and it compounds with each generation which is not necessarily a good thing. When my grandmother died, my dad just took out all this personal stuff that was hers and put it in boxes and took it to his house. I’m talking about things like photo albums and graded papers from school, very sentimental things with a lot of intrinsic value, but nothing beyond that. Then when my dad passed, my mom was going through all his stuff. My dad had my grandfather’s flag, a flag that my grandfather got in like Iwo Jima or something. He fought in the Pacific and World War Two, and he had a flag, and then my grandmother had it, and then my dad had it. My mom’s like, I don’t know what to do with this stuff. So, my sister, who’s the youngest and probably most responsible of the three of us, took all of that stuff from my mom, so now she’s got boxes and boxes, and she’s like, Tim, I’ve opened some of these photo albums, and I don’t know who these people are. They’re not labeled. There’s nothing written on them. She’s like, no one alive knows these people. I don’t know what to do with them, but I don’t want to throw them out. I’m like, I don’t know what to do. That’s a really interesting thing, like, what does my sister do with the photo albums of my grandmother?
Yeah. Well, there’s two edges to this. There are a few things I have that were directly from my grandfather on my dad’s side. One is an old radio that’s got to be from the early 30s, I’m thinking somewhere between 1930 and 1940, and it needs some work. I intend to fix it up eventually, but it’s sitting in the foyer of my house, so when you walk in, it’s the first thing you see. To me, there’s a lot of symbolic meaning around that device. He grew up in a tough time and in a tough household and didn’t have a lot of support from his parents for certain things. I mean, his dad had been an orphan. When my grandfather realized what he wanted to do with his life, he wanted to become a mechanic. This was at like age sixteen or seventeen, and there was this trade school. He was like, dad, I got this. This is what I want to do with my life. I feel it in my bones. And his dad’s response was something like, well, you’re gonna need to figure out how to get there, you know, there wasn’t the family shuttle stuff that we have going on today. He was just really oppressed, so when he bought this radio, it was the first demonstration of his independence. Because it has all this meaning, I’m really glad I have it, and I’m gonna keep that forever. I would never get rid of that, I wouldn’t sell it even if I could get a lot of money for it. It just has a lot of sentimental value to me. I have some of his tools that I use, and I think about him when I use them, but outside of that there’s probably a lot of stuff that I could have ended up with, and it would have been more junk to get rid of someday, so I think it’s being selective and recognizing those traps.
Yeah. I think, too, there’s some nostalgia that’s kind of insidious and a little bit more dangerous, at least for me. There’s being nostalgic about very personal things or items, like I totally understand where you’re coming from on the radio. That totally makes sense to me. I have to be careful as I start getting nostalgic for times or experiences I’ve had, and that’s a slippery slope. I almost feel like it’s dangerous to go down because that’s never gonna happen again, that experience will never be that way again, whatever it was, from whatever moment in my life. What I’m trying to work through, I think this is a good start, I’m trying to explore more in fiction. Over the past literally couple weeks, I’ve been working on a few projects, just project ideas really, and their time travel stories, and I’ve found it feels like a healthy outlet for me. I can explore those times and those experiences in a productive way and create some art around it and not be stuck in it mentally, so I’m at the very beginning of that. I have no idea where it’s going to go. I don’t know, in two weeks, I could be off on some farm trying to find a portal in 1989, you might have to rescue me. As of right now, it feels like it might be a way to process some of that stuff.
That sounds very healthy.
Alright, if you don’t mind, what are some events or moments that you find replaying in your head or that you’re drawn back to?
Yeah, I’ll tell you sort of what sparked this for me. Do you know anything about the Outlander series, either the book or the television show?
Okay, well it doesn’t matter if you don’t. It’s extremely popular. It’s categorized as a time travel romance, and it’s about this woman who is British. She’s visiting in Scotland, and she finds a portal that transports her back to 18th century Scotland, and it’s fascinating. I think what I’m really drawn to is this idea of the historical period, so I’ve been thinking a lot about that, and what I find the period for me is roughly like 1988 to about 1994. Not surprisingly, that’s when I’m like ages seventeen to twenty-three. I find myself thinking a lot about those times. Not freshman year high school, that was brutal, but like senior year of high school, the summer between senior year and college, my college experience, my first couple years in the professional world after graduating from college. That window of time feels like it’s something I want to explore, so in one of the fiction projects I’m thinking about doing is I’m thinking about setting the quote unquote modern time in 1994 and just let myself have fun with that and go back and research the hit songs and the television shows and the words people were using and sort of incorporate that into the fiction. But that’s, for me, the most nostalgic. It’s weird because I don’t have a lot of nostalgia for anything after age thirty or so. I have nice memories, but I don’t feel that same sort of pull that I did when I was like seventeen to twenty-three. How about you? Do you have any sort of times that you think about more than others?
Probably similar, and I think I’ve heard other people talk about that time period. I think that range that you’re talking about, you know, sometime in high school. For me, it would probably start sophomore year and then up through kind of like mid twenties. That’s a common timeframe we go through. Obviously, all the different periods of our lives are filled with different kinds of growth, but that time period, we’re really plugged into culture, to whatever it is that we like. By that age, you figured out what music you like, what movies you like, what fiction you like to read, all that kind of stuff. You’ve kind of started to figure out who you are. You’re looking ahead and seeing possibilities, so all the doors still feel like they’re open. The stuff I was talking about, you know, feeling the recovery time, you could do any kind of physical activity and not worry about it. It’s a great time in people’s lives generally, so it makes sense. I think it would be interesting to explore, why does that change so much? What is it about life that starts to steal some of that away? Maybe it’s getting rejected for jobs or realizing that it’s a little harder to live in your dream scenario than you thought. I don’t know what changes that.
I wonder if there’s any sort of biological basis for that when you get into the neuroplasticity of the brain and not being fully formed until you’re a young adult, like I wonder if that plays into it at all. It’s some variable that’s involved in that feeling. Well, I’d like to put a bow on this and just say if you’ve turned fifty recently or fifty’s on the horizon and you’re having strange thoughts, you’re not the only one.
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Transcribed by https://otter.ai
Generation X, Your AARP Card Awaits – The advocacy group for the over-50 set welcomes a mercurial generation that never wanted to grow up in the first place. By Alex Williams – https://www.nytimes.com/2021/04/24/style/generation-gen-x-aarp-oscar-ad.html
AARP ad – https://youtu.be/YuPvL3aVy4c
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