Teaching Transformations Podcast Episode 5: How GenX Will Save the World

Teaching Transformations

How GenX Will Save the World

In this episode of Teaching Transformations, Tim and Ryan discuss how our generational mindsets differ and the influence they have on the approaches we take to certain situations. The guys consider how growing up GenXers has shaped their personalities and work ethics.

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!


Tim  0:00  

What’s up, The Greevil Keys?

Ryan  0:00  

I don’t know why it gives me random names like that. I’m new to this SquadCast thing.

Tim  0:06  

Yeah, I think it’s just how the system is set up or you don’t set your profile name and it just randomly assigns something out to you, so yeah, Mr. Keys is with us today.

Ryan  0:15  

It does come up with cool names. I will say I appreciate the creative names that it makes up for me.

Tim  0:19  

Yeah, you were trying to log in before as Resonant Disonator or something like that, I don’t know. So, we have a pretty interesting conversation today.

Ryan  0:43  

I’m excited about this. This is a cool topic that you’ve picked out for us. Well, I don’t want to steal your thunder.

Tim  0:56  

Yeah, I don’t know if it’s gonna be a thunderous rant or sort of an intellectual exercise. I’m trying to think of where to start with this. I guess we could start with us. We were both born in the early 70s, correct?

Ryan  1:13  


Tim  1:14  

Me a few years before.

Ryan  1:16  

’72 for me.

Tim  1:18  

’71. Alright, so maybe we’re only a year apart. We are clearly like, dead center Generation X. I think what’s interesting about this is, I never even thought about a generational label until a few years ago, and I think that in itself says something about Generation X. You and I have talked about this before, have you gone to any high school reunions?

Ryan  1:50  

I have, I’ve gone to all of them. The funny thing is, I actually planned our first one. It was so much work, and it was before social media and all of that. I was like a private investigator trying to find people’s addresses and stuff, and I had to literally call them on the phone. That’s how long ago this was.

Tim  2:18  

Two-year high school reunion or something?

Ryan  2:22  

Yeah, I think it was ten, but it was so much work. I was like, I’m never doing this again, and I told everybody that, so now other people have picked up the other ones. I think, yeah, actually, last year would have been our thirtieth, and we just didn’t have it. I don’t know if it was Covid or because no one’s picking up the mantle. Yeah, I’m kind of into that thing, but I know where you are going–you probably have never been to one.

Tim  2:48  

No, and it’s not just me. There have been a few attempts, and I graduated in a class of like seven or 800 people, so there are enough people who could take the ball and run with it if they wanted, and we have not had a single official reunion. I don’t know if it was last year or the year before, it was our thirty-fifth. Someone set up a Facebook group, and there were people in it. Then, they had pictures from the event, and there were like fifteen people that showed up, and I’m like, that is such a Gen X thing, like we were just not joiners. We’re still somewhat cynical. We’re individualists. We’re not like big community people, and it’s a funny observation. The reason we want to talk about this is because, you know, we really are in a sandwich generation. I’m gonna sound like a name dropping asshat, but I have to do this. The trigger for me came a few years ago when my dad passed away, and I had this moment. This sounds silly, you know, he died when I was forty-seven, and I had this moment of like, now I’m on my own at forty-seven with a family, my own two kids, a career, whatever. I was like, okay, now I’m on my own, I have no one to get my back. For the Writers, Ink podcast recently, the big interview, I was really excited about this, Matthew McConaughey. We talked about that, and he said, yeah, you got to own your shit. You’ve got to kind of step up and be responsible for it now, and I kind of feel like that’s where we are generationally. Do you know where I’m going with this?

Ryan  4:45  

I do, yeah, and I think you’re right on. If you look up information about Generation X, I mean, you’ll find words like independent, self-determinant. Those are sort of positive words, like I view the most positive words of our generation as it’s aged, but if you back that up, those same adjectives probably look different when you’re nineteen, right? You’re just rejecting everything you’re not, like you said, you’re not joining anything.

Tim  5:25  

Guilty as charged.

Ryan  5:26  

Right. So, that’s kind of what I’ve found as I’ve dug into this is that I do think there is something to these generational characteristics, but I think they age just like anything else does. Some aspects probably take on more positive characteristics, and some go the opposite direction, I’m sure. Our sense of sort of rejecting everything, everything sucks, you know, like that. I think what that turns into over time is, you realize, no one’s there for you. It’s kind of like what you’re saying about your dad, like, you have to determine whether it sucks or not because you just assume that whatever is handed to you is going to suck. We realized early on that we had to kind of create whatever beauty we wanted or needed.

Tim  6:26  

That’s deep-seated, too, you know, I’ve heard us called the latchkey generation. We were kids who grew up without the internet, without parental supervision, for better or worse, left at home for days or hours at a time to get to our own devices, and we had to do that. We had to be responsible for ourselves, and it’s almost unthinkable parenting today. Could you imagine? Latchkey parenting today would be almost unthinkable, well, in our circle, right? In our community, it would be unheard of.

Ryan  6:57  

I was so unsupervised during my entire childhood. I remember days, and I lived in a suburb, so it was a safe place. I don’t think my parents had a lot to worry about, but I mean, I would disappear in the morning and literally be gone until dark, and my mom had no idea where I was. I mean, I remember a day when we decided to sneak down into the sewer system and the drainage sewer pipes.

Tim  7:26  

What could possibly go wrong there?

Ryan  7:30  

We had flashlights and stuff, and we were down there for hours, going into smaller and smaller pipes. We actually went so far, we sort of got stuck. We were like, we don’t have time to go back. We noticed an opening out at one of our roads, and we went out there. It just so happens that one of our friends riding by on their bike heard us yelling and came and lifted the grate up for us.

Tim  7:56  

And then the clown with the red balloon showed up and it was all over.

Ryan  8:01  

But yeah, unsupervised, left to sort of create our own realities, right?

Tim  8:07  

Yeah, and let’s not sugarcoat it, like there are problems with that approach. We just said, yeah, individualistic, self-determined, aspirational. Those are all very positive attributes, but the other side of that coin is detached, uncaring, unsympathetic. That’s a reality, too, so I don’t want to paint this as like putting Gen X on a pedestal. What’s interesting is that as we have aged, we are now sandwiched between two generations at war with each other. I don’t think that’s an understatement. If you’re a Gen X and you have friends who are Millennials and friends who are Baby Boomers, you will know there’s a strong dislike between those demographics. You have Baby Boomers who believe that Millennials and Gen Z are just whiny snowflakes and they take things too seriously and they hate cancel culture. That’s sort of the perspective of the Baby Boomers towards Millennials. Millennials look at Boomers as, you guys caused all the problems, all the social unrest, all of the economic problems–it’s all because of you, and Boomers continue to drain resources. They’re both right, by the way, and here we are in the middle. As we’ve come into middle age, I feel like we’ve got our hands up on both sides, trying to be the sane, logical parents, and part of me is like, when the hell did that happen? When did I have to become responsible?

Ryan  9:53  

Right? Yeah, it’s a weird place to be because especially given where we started, where we were just rejecting everything, and now we’re looking around and we’re like, wait, we’re kind of in charge of stuff now. I mean, we have to make stuff work now. It’s interesting. You talked about this sandwich stuff, and I read a few articles last night, some of which I’m sure will be in the show notes, but this line stuck out to me. “Boomers live in the past and have ransomed the future. Millennials fear the future and are ignorant of the past.” I don’t know, I read stuff like that. I’m like, that does ring true for me. I mean, that sort of sums it up in a statement.

Tim  10:43  

Yeah, and kind of circling back for a second, I always knew, mostly because of Billy Idol, but I always knew what Generation X was. I didn’t read Copeland’s book in ’91 when it came out. I don’t think I read that book. It’s called Generation X, that’s where the label came from. Yeah, I don’t think I read that until the late 90s, early 2000s maybe, and I kind of, you know, sloughed it off. I didn’t even think much of it, and it goes back to who we are. I didn’t identify with a generation, I wasn’t going to high school reunions, I wasn’t hanging out with groups of people who are like me, and even now, it’s starting to change, but if you go and look on iTunes for Generation X podcasts, there aren’t that many, or they’re comparatively speaking. It’s only been the past few years where I’ve really started to take notice of these generational differences and feel like a Gen X, and I never carried that flag, and I don’t wave that banner, but it’s almost hard to deny now.

Ryan  12:05  

Yeah, well, isn’t the X like, didn’t that come because there was nothing they could pin us on? We had no culture identifiers. Basically, it was like, fill in the blank here. I didn’t read that book.

Tim  12:22  

Yeah. You can tie into music, music is a good parallel, right? If you look at the music of Generation X, like, technically, you could start with the 80s new wave or the new wave of British heavy metal all the way up through mainstream pop like Michael Jackson and Madonna to 80s hair metal to 90s grunge to electronic music to the alternative, right? Remember, alternative music came about because it was just the alternative to what mainstream was listening to, but it didn’t have any anything to tie it together. You could listen to Cake and The Offspring and Nirvana, and it was all alternative, and those are three very different bands.

Ryan  13:12  

I think it’s funny that we have this term alternative, when you just described the whole range of music during that time period. There was no like specific characteristics, but we still had this alternative category that somehow bucked the system. It was different than the undefined rest of it.

Tim  13:34  

Yeah. We had to push back against things we didn’t even know we were pushing back against.

Ryan  13:40  

I saw somebody present several years ago on intergenerational differences, and I think the statement they used for Gen Xers was they question questions. I’m pretty sure I remember that right.

Tim  13:56  

That sounds about right, for sure.

Ryan  14:00  


Tim  14:01  

So, why are we having this conversation on Teaching Transformations?

Ryan  14:11  

Why are you and I having this conversation? Boy, he put me on the spot there. I mean, I think because there are a lot of us who kind of are like in this category of defying categorization, and I think that leaves a lot of us without really big stakes in the ground. There are people who are our age who are in some ways still mapping a path, like they still feel there’s a sense of possibility. It hasn’t been overdefined. We didn’t just like step into our career path and just follow it without sort of thinking about other things. I don’t know. That’s what comes to mind for me.

Tim  15:21  

Yeah, no, I appreciate you answering that. I know I put you on the spot. I’m overgeneralizing, you know, and looking at the Boomers, it almost feels like the Baby Boomers are at this point. They’re content to just ride into the sunset, like they’ve done their thing. They gave us Woodstock, and they ended the draft. They did their part. I feel like there’s a passing of responsibility from Baby Boomers. I don’t feel like Baby Boomers right now are the ones who are going to change the world, right? It’s not realistic to expect that. Then I look at Millennials, and I think you guys are so cute. You’re all gonna save everything all the time. This ties into that snowflake sensitivity issue a bit in that I feel like in conversations with Millennials, everything I say is somewhat off-putting, you know. I don’t even realize it, like certain things I say, in the way I say it, are somehow offensive, and I recognize that, and I understand the importance of inclusion, right? But, there’s part of me that thinks, you guys are so scattered. You’re not going to accomplish anything. You try and do everything, you’ll get nothing done, and that’s what it feels like. Whether you’re looking at climate change or racial inequality, or economic inequality, it feels like everything is turned up to eleven all the time. I don’t think that’s sustainable. I don’t think that’s realistic, as far as like making a real difference and turning corners on some of this stuff. I’ll give you a concrete example, and I’m not denigrating this, or I’m not making fun of it. Last year, when we had a lot of the racial strife, you know, people were changing their Instagram profiles to Black Lives Matter, and I’m like, what’s that doing exactly? Maybe it’s that cynical Gen X in me, but what is that doing? Even so much as demonstrating or protesting or parading, those are all positive things, and that’s raising awareness. I come back to this idea of that, and maybe this is an element of our age, but I kind of feel like we’re in a place now where the way we’re going to make change is by looking at our neighbor and helping out the people next to us. It’s not necessarily being wrapped up in these global movements that look really good when you’re virtue signaling, but they don’t really accomplish anything.

Ryan  18:30  

That’s really interesting. I definitely see what you’re saying. The word that comes to mind for me is symbolic. The Millennials seem to be really caught up in the symbolic, and I think our generation, I wouldn’t say we reject that necessarily, but we want to see more substance where we want to see more action. Maybe I’m getting too caught up now in these generalizations about the generations, but there’s definitely a high amount of symbolism floating around. This is the culture of outrage. That’s not relatable to me. I think it’s not relatable to a lot of people who are our age, and it’s not that we don’t care. I agree with people about these movements. I agree there are racial problems that need to be addressed. It’s not like I don’t think that’s a problem. I just don’t think the solution is me changing the label on my Instagram account.

Tim  19:52  

Yeah. Do you think social media is an important element of this? We use social media, but we didn’t grow up with it, and Baby Boomers never really used it, and Millennials have always known it. Do you think there’s something to that?

Ryan  20:12  

I think there has to be. It’s just part of the fabric of their lives, and it’s a big part of how they, I think, get validation from others. It’s how they signal support for things. Honestly, it’s probably the biggest differentiator between our generation and the ones that are following us for sure.

Tim  20:38  

So, maybe we would have cared if we had that same access to each other, like, I don’t know. The closest I came to signalling, which I still do, is wearing my favorite bands’ t-shirts. That was kind of it.

Ryan  21:00  

Well, think about my sewer pipe story. In today’s world, you just reach in your pocket and pull out your iPhone and call your buddy or call somebody and say, hey, I’m stuck. We didn’t have that.

Tim  21:15  

Yeah, I think to the way I’m sort of channeling this, it’s not really an epiphany. That sounds too dramatic, but it’s sort of this realization, and maybe an acceptance. Maybe this is part of middle age is a certain level of acceptance of how things are, how you are, and your place in this world. It’s not defeatist, but I also don’t believe that, like, if I want to slam dunk, I’m gonna slam dunk. That’s past me, that’s never gonna happen. There are certain aspects of my life and certain things that I’m not going to do, and I’ve accepted that now. With that acceptance, I think it’s narrowed my focus a little bit. So, for my author community, I know a lot of people in that industry, and they are all over the spectrum as far as ages and interests and passions go. What I notice is, the younger people there are more interested in movements, and they want as many people part of something, and they all want to find each other and they want this really big community, and I’m starting to use this language in my author group. I’m calling them my family. I’m not concerned about those big movements in those big communities, like those authors can have those. I want to just work and help and grow with a small, tight-knit group of people that I can count on who aren’t worried about that external noise and validation and signaling.

Ryan  22:50  

Yeah, and what I was gonna say about that was just the whole thing about numbers. Think about our recent president and his obsession with tweeting, and he was really into using social media, but he was also really consumed with those numbers. I mean, remember how obsessed he was about wanting to make sure everybody knew how many people were at his inauguration? He’s not of that generation, but he’s kind of in some ways played to the values of that generation, and I do think there’s something about numbers. I think for us, yeah, we’re less moved by that. I feel the same way. I don’t know if that’s a generational thing or not, but maybe it’s partly an age thing. Maybe it’s over time you realize, I really just want to have an impact on people around me. I don’t need to be standing on some giant stage to do that, you know, I do that in smaller communities, and especially those of us who’ve been in education, we’ve had a number of those experiences for a long time where we have had impact on people’s lives in small groups, so we can build on that.

Tim  24:16  

It’s also struck me too, that I’ve tested as an INTJ on the Myers Briggs the past five or six times I’ve done that over the past ten years. I feel like that aspect of my personality is pretty hard wired at this point, but part of me also wonders how much of a generational influence there is because when I look at sort of classic introversion and I look at characteristics of Gen X, they’re pretty complimentary.

Ryan  24:48  

So are you saying you think that if we had everybody in our generation take the Myers Briggs, they would probably be some common theme behind them or certain letters?

Tim  25:02  

Yeah, I wonder where we would sit on a spectrum as a whole. Again, that’s a broad generalization, but there does seem to be this idea of looking within, you know, focusing local as opposed to global, not being part of things like those. Those are characteristics of both introversion and Generation X.

Ryan  25:26  

Yeah, there could be something there. I always come out as INTP, and I hate this kind of categorization. I mean, I hate that there’s some tests that peg me in some way. I just feel like, oh, I’m too complex to be defined by your alternative. The funny thing is, I’ve probably taken it, I would say, maybe five times now in my life at different periods. I think it’s got me the same every single time, and even as I’m taking it, I’m thinking about every question, and I’m like, okay, I could answer this differently tomorrow because I’m right on the fence, but I’m going to answer it this way, so I feel like I’m waffley about a lot of those questions, but it gets me the same every time in terms of that introversion being a common characteristic. Who wrote that book, Quiet: The Power of Introverts?

Tim  26:35  

Susan Cain?

Ryan  26:35  

Yes. I think she got into that a little bit. I do think there’s sort of a wave of introversion, and you have to wonder if that’s related to events or just what unfolds in the world during the time that you’re growing up. I don’t know why I think about this, but like we all were sitting in class the day the Challenger exploded. There’s a certain number of common experiences that defined our generation, I mean, MTV, you know, there’s a lot of stuff like that would have to create some sort of common denominator, I would think, among all of our personalities, and the same goes for every generation.

Tim  27:26  

It’s an interesting place to be. I’ll go a bit meta for a minute because when I reached out to you to kind of start this thing that we’re doing, Teaching Transformations, I had already had a false start on something I had played around with doing, something in the personal finance space which was related. It wasn’t completely different, but it was definitely a different angle. It was looking more at financial decisions that you can make to prepare yourself for retirement, and it was a false start because once I started doing it, I’m like, this isn’t me. This doesn’t align with what I want to do. If you look at that space, it really is about the numbers and the global movements. You look at guys like Dave Ramsey, you know, is probably the best example. Everyone knows Dave Ramsey as his personal financial guru. There are a whole string of people who came after him who have blogs and podcasts, and they’re all about the metrics and the numbers and reach and platform, and that just doesn’t matter to me. Again, I come back to this idea. People talk to me about Kevin Kelly’s 1000 True Fans all the time, and for a while, that was a great sort of charged object that people in my industry used as a Northstar. They said, okay, if I can just get 1000 true fans, I can make a living at this because a true fan is someone who’s going to purchase everything you create or sign up for every service that you offer. They’re your rabid fans, and if you have 1000 of those people, you can make a decent living on it. For a while, I kind of bought into that, and I’m not saying it’s false, I think it is true, but I came to this realization that that’s just a lot of people. I’m not interested in being part of that many people, and that’s why I keep talking about more of a clan or a family as an approach, and what I want to build and what I want to help people build are these really small communities where everyone knows each other. You have a direct positive effect on someone else’s life, and by doing that collectively, that will save the world, but that’s different than standing on the big stage and trying to gather the masses.

Ryan  30:07  

Well, I think it’s because the ideas get watered down the more people that are involved. The core ideas end up getting shaped to sort of match the collective whole, so they kind of lose some of their purity that way, so, yeah, that makes total sense to me. It’s funny you bring this up because I was just listening to your Writers, Ink, one of your episodes last night, and I think this was the one with Zack joining you. You guys were talking about your lists, and Zack was sort of talking about how he’s always had a really tight list and sort of how he generated that list and what it meant for him. It sounds like it really worked because those people were all sort of on the same page naturally, and he wasn’t trying to build something that appealed to this gigantic list of people somewhere. I think you’ve been through that transformation. In that same episode, you talked about the fact that you had a list, an email list, and it started off really, really big. Then, over time, you just made it smaller and smaller. That’s just an interesting progression because that sort of goes against this trend,we’re talking about where people are trying to build more and more and more people, but what does that really mean? What’s being given up in that progression?

Tim  31:48  

Yeah, it’s counterintuitive. I have good friends in the author space who are now making six and seven figures, and they’re doing that by becoming sort of these global brands and doing that by creating lists of tens of thousands of people, and they’re all about, how many posts did this get and advertising to millions of people. I played that game for a few years, and it wasn’t me, and I wasn’t good at it. Eventually, I started going in the opposite direction like a true Gen X, or I was like, well, if everyone’s gonna be building their list, I’m gonna call mine. I don’t want the most people, I want the right people, and that’s not sexy because it takes a long time. It’s not a hack, and it’s not something you can purchase. I think it’s something that we’re very aware of–even this podcast is not going to be a mainstream listen. That’s not what we’re trying to do. We’re not looking for, you know, hundreds of thousands of people. If people come to us because they connect with what we’re talking about, that’s great, but that’s not our intention.

Ryan  33:08  

I don’t think my mom’s even gonna listen to this.

Tim  33:12  

Well, my wife won’t.

Ryan  33:14  

We’ve established that, yeah. It’s more meaningful that way. You can have a more meaningful relationship with a smaller group of people around tighter parameters, so it makes total sense. I want to put you on the spot.

Tim  33:38  

Go for it.

Ryan  33:40  

So, you were talking about how you pivoted from that first idea to financial stuff. That was really all about numbers and everything, and it didn’t allow you to forget the words you used already, but you said something like that’s not what you wanted to do. That wasn’t aligned to what you wanted to accomplish, and I’m just gonna ask you straight up, what do you want to accomplish?

Tim  34:14  

Like with this?

Ryan  34:16  

With anything. What are your goals?

Tim  34:22  

Well, I hate goals, so I don’t set goals, but I know what you’re asking me. I think you can ask me what I want, and I already have that. I want independence. I want to be able to determine what I want to do with my time, and in doing so, I want to be able to provide for my family. I want to have a healthy family and healthy relationships, and I have all that right now.

Ryan  34:52  

That’s awesome.

Tim  34:57  

But it sounds like a jackass of an answer. I know what you’re saying, like, why am I doing it if I have all that? Why am I doing this?

Ryan  35:06  

Well, I think that question is kind of always out there. Maybe I didn’t really think about my motivations for asking the question. It just occurred to me that would be a fun question to throw at you. I found myself a number of times looking at people who seemed to have achieved what they were looking for, so I always have this question. Well, then why are you doing this? You know, like you already have what you want, so I think I kind of have that question about you.

Tim  35:44  

That’s a legitimate question. There’s the bigger picture answer I stand by, which is I have all that. The smaller picture answer is that I’m not entirely financially independent yet, so part of me wants to make sure that I am thinking about my future in an ethically sustainable way. That means building small, close relationships or close relationships with a small group of people, being able to serve them and make a little money while I do that. I don’t have aspirations to retire to a mansion in Florida or buy a private island in the Caribbean. When our youngest goes to college, you know, Joy and I might be digital nomads. We have a very low bar for happiness. In doing this now and having what I have right now, is the lifestyle that I want, and what I’m close to but I don’t have is the financial security to support it. It’s close, and I’m realizing that at the same time, I’m having this realization that I have one more block, so to speak, of a career left, or one more era of myself, one more chapter. Everything I’ve done now has been focused on me, which I think is natural, and now I want to build something for others. I genuinely believe that. My teaching career was about getting myself professionally set and getting my family taken care of, and then my author career was about pursuing my own creative passions and being able to be successful with that. Now I feel like, okay, I’ve got those things. Now, what I really want to do is help other people along that path while at the same time looking ahead to what I’m going to do with my retirement and how I’m going to fund that. That’s why I’m doing what I’m doing. I could have doubled down on the author stuff and gone the route of some of my friends and really blown up my platform. When I say blow up my platform, meaning like, go global. You know, major conferences and speaking tours and that kind of stuff, but that doesn’t feel like the type of work I want to be doing on a day to day basis which would totally defeat the purpose of doing it. I love the ability to sit here in my room, in my office, and do what I want to do and not have to be on a plane to such and such and not have to be on a stage here. If you’re not careful, you can come full circle right back to the thing you’re trying to avoid.

Ryan  38:43  

Well, and I won’t use the word goals because you don’t like that, but I’ll just say your interests and your desires are complex, right? It’s not one dimensional. If it was one dimensional, it’d be easy. If you just wanted to make money, you could just go do that. You could really hunker down and double down on the stuff you had going already, but I think your interests are bigger than that. I think a lot of us feel that way. We want both, and you know, it’s not one thing. I don’t have your level of independence. I think that’s something that we’re capturing here is sort of, in some ways, a juxtaposition between where I’m at and where you are in terms of conventional sort of career. Not path, but career, where we are right now on our journeys. I’m definitely in a much more conventional place. I mean, I’m actually sitting here feeling a little bit guilty because we’re recording this during a workday and even though I worked until, you know, nine o’clock last night, it’s just I feel a little guilty about this. I think what I really relate to in your story is, you want everything. You want that independence, but you also want to make a difference. You want to have an impact on people on the world in the best way that you can, and I think that’s something that a lot of people are gonna really resonate with. I don’t know why I’m thinking of this, but I used to listen to a lot of Bruce Springsteen. In a lot of his early shows, he did a lot of storytelling, but he was relating this conversation with his parents, like how his mom wanted him to be a doctor and his dad wanted him to be a lawyer. He was like, what I just couldn’t explain to them was I just wanted everything, and I knew what he meant by that was not just like, hey, I just want to be a rock star. What he wanted out of his life was multidimensional. If you look at his career, I mean, he could have stopped. He’s not doing it for the money anymore. He doesn’t need to keep doing concerts deep into his 60s. His career has been very multi-dimensional, and so is his life. I just think it’s funny that he kind of understood that at such a young age.

Tim  41:29  

Yeah, and it could very well be just a maturation process. I think the fact that Gen X was pretty cynical and disconnected in our 20s. It was basically like, keep your head down, worry about yourself, just do your job, whatever. Now, I think we’re maturing into a different phase of our lives. I think there are a lot of us right now who are looking for something more or all of it, right? It’s not enough anymore. It’s not enough just to kind of go and do your job and come home and collect your paycheck, whatever that happens to look like for you. It’s just not enough. There’s scientific evidence of this whole happiness curve idea that, you know, we hit a point in our late 40s and early 50s where we kind of bought them out, and because we’ve accomplished a lot of the stuff we’ve all set out to do, like, I’m sure you’re very proud of what you’ve accomplished. You have a long, prestigious career in academia. You are raising a family of three, and you’ve got a nice house in a nice neighborhood, you’re not worried about where your next meal is coming from, you’re successful, but you have this itch, you’ve got this yearning now. I think that’s a pretty common thing, and it’s lining up with a generation that has been historically pretty cynical and also the scientific part of hitting the bottom of that happiness curve in your late 40s, early 50s. I think that’s why we’re here, and I think that’s why people are probably listening to this.

Ryan  43:16  

Well, I think about, I find this in a lot of music I listen to and movies. I was just watching Risky Business again the other night for some reason. I pulled that out, and just the soundtrack that lives behind that movie, and all the different sorts of suggestions that are made but not fully realized, you know, they’re not brought to the fore. It gives you a lot to think about. There’s always more there. I think that’s the way I think about things. There’s always more going on below the surface, and I want to go there. I want to find a possibility. When you’re younger, maybe you just think about that stuff a lot, but as I’ve gotten older, and I’ve accomplished certain things, and I’ve figured out how to actually make certain things happen in my life, it’s like I can combine those two ideas. I do feel like there’s always this sense of possibility, and there’s always more going on below the surface, but I also feel more empowered to bring it to the surface and turn it into something, I guess maybe that’s the kind of thing that happens when we age.

Tim  44:35  

Yeah, I agree with that. I think for me, there’s a third variable there, which is the time. While those two things are going on, you’re also saying , okay, but I’m not twenty anymore. I don’t have fifty years to make this happen, so it also creates a little sense of urgency.

Ryan  44:53  

Right, and that’s what I’m feeling a lot. I’m feeling that more and more, and the other side to the time piece is we see ourselves having more time. We literally have more time. I mean, if for those of us who’ve been shuffling kids around as they get older, and they can start to drive themselves, you know, that’s less time we’re spending in the car. That’s less time we’re spending doing other other things, and I don’t begrudge any of that time, but I’m looking now, my youngest is a freshman in high school. In a year or so he’ll be driving, and then, in three years, he’ll be going off to college. I look at that coming, and I’m like, I don’t even know how to relate to that anymore. Just that sheer amount of time that will be handed back to me at that point. So for me, I’m actively trying to figure out what am I going to do with that because it ties to the other side of time you were just talking about, like that urgency piece. I’m going to have more, and I feel more urgency about making use of it. I’m looking ahead, and I’m like, I gotta make the most of this, I really have to start building stuff now, so that I can make the most of what is going to be there.

Tim  46:18  

Yeah, our youngest is in the same class. You and I are going through that together, and I’m having a lot of those same feelings. You know, I’ve joked around with people who are not parents, and I think back of how much time I wasted in my twenties because we didn’t have kids. Then, when you have kids, you realize how valuable that time is, like specifically the time that you have to yourself and you don’t waste it anymore. Now that we’ve like wasted time and seen what that looked like, and now had this period of our lives where our time has been allocated for us, and now we’re looking just ahead on the horizon and seeing it coming back. It’s an exciting proposition, and I think for people who are teachers and have a skill set as we’ve talked about, that can apply in many different areas. Now’s a good time to be thinking about that time that you’re going to get back because you’re going to get it. Hopefully you’ll get it back for a couple of decades.

Ryan  47:24  

Yeah, but it’s not unlimited.

Tim  47:27  

It isn’t.

Transcribed by https://otter.ai


Why Generation X Might Be Our Last, Best Hope – https://www.vanityfair.com/style/2017/08/why-generation-x-might-be-our-last-best-hope 

OK, Slacker. Can Gen X Save The World? – https://www.forbes.com/sites/solitairetownsend/2020/01/07/ok-slacker-can-gen-x-save-the-world/?sh=70ecb29f7399 

IN THE WAR BETWEEN MILLENNIALS AND BABY BOOMERS WE HAVE FORGOTTEN ABOUT THE WORK-HARD, PLAY-HARD GENERATION X – https://www.independent.co.uk/life-style/health-and-families/millenials-generation-x-baby-boomers-a7570326.html 

X Saves the World: How Generation X Got the Shaft but Can Still Keep Everything from Sucking – https://www.amazon.com/dp/B0013TX7I4/ 

Transformations – The free weekly email with the best personally curated resources to help teachers in their late forties or fifties to design a post-academic life. – https://teachingtransformations.com/ 

Teaching Transformations Podcast – https://teachingtransformations.com/podcast/ 

Intro and outro music by Penthouses. “Come to Ohio” from The Weatherman album available on most music platforms.

*Full disclosure: Some of the links are affiliate links.