Aug. 17, 2026

Episode 54 -- When Hard Work Isn’t Enough: Were We Sold the Wrong Version of Adulthood?

Episode 54 -- When Hard Work Isn’t Enough: Were We Sold the Wrong Version of Adulthood?
As the Dinesens Turn
Episode 54 -- When Hard Work Isn’t Enough: Were We Sold the Wrong Version of Adulthood?

Go to college. Get the degree. Work hard. Build a career. Save for retirement. Do all the right things, and everything will work out. At least, that’s what we were told. In this episode of As the Dinesens Turn, Jason and Tracy wrestle with their growing cynicism—or maybe realism—about work, education, money, careers, and the promises their generation grew up believing. Both came of age hearing that a college degree was the ticket to a secure future. Jason remembers a high-school guidance ...

Go to college. Get the degree. Work hard. Build a career. Save for retirement.

Do all the right things, and everything will work out.

At least, that’s what we were told.

In this episode of As the Dinesens Turn, Jason and Tracy wrestle with their growing cynicism—or maybe realism—about work, education, money, careers, and the promises their generation grew up believing.

Both came of age hearing that a college degree was the ticket to a secure future. Jason remembers a high-school guidance counselor insisting that it didn’t even matter what the degree was in: just “get that piece of paper” and you’d be set for life.

Tracy believed just as deeply in education and the idea that if you worked hard, followed the rules, cared about your students, and did what was asked of you, the system would reward that commitment.

Then reality intervened.

They talk about watching workplaces reward hard workers with more work instead of more money, seeing talented employees become too valuable to promote, and discovering that institutions don’t necessarily return the loyalty their employees give them.

And then there’s money.

Even as they’ve become more successful, Jason and Tracy find themselves asking a frustrating question: Why does it still feel like there’s never enough?

Housing costs more. Education costs more. Everyday life costs more. The old stories about working some overtime to buy a new car with cash sound like tales from another universe.

These questions have become more urgent as they talk with their own kids about what comes next.

Does university still automatically make sense? Is taking on massive debt for a degree worth it? What happens when a teenager has already earned professional training and hundreds of hours of practical experience before finishing secondary school? And how do parents advise a child about a future career when AI and technology are changing entire industries faster than anyone can predict?

Maybe the hardest realization is that hard work matters—but hard work alone doesn't guarantee the outcome.

Luck matters. Timing matters. The economic system matters. And sometimes you can do everything you were told to do and still discover that the promised destination isn't there.

It’s admittedly one of the heavier episodes of As the Dinesens Turn. But these are also conversations happening around kitchen tables everywhere: between spouses trying to understand their finances, workers questioning their careers, and parents wondering what advice they should give their children when the old advice no longer seems adequate.

Jason and Tracy don’t pretend to have the answers.

They’re just increasingly unwilling to accept the old answers at face value.

Also, Stan the dog makes an appearance, Jason attempts to argue that being held back in kindergarten makes him basically a Millennial, and Tracy informs him that being born in 1978 does, in fact, make him Gen X.

So it’s not all doom and gloom.

In this episode:

Were Millennials and Gen Xers sold an outdated formula for success?
Does a college degree still deliver what previous generations were promised?
Why hard work can lead to more work instead of advancement
The financial squeeze facing families even as their incomes rise
Helping teenagers decide whether university is actually the right next step
Preparing kids for careers in a world being rapidly reshaped by AI
Tracy’s disillusionment with higher education
Jason’s growing economic cynicism
Why success involves more than simply working hard
And the important question: Is Jason actually Gen X?

Bottom line: Maybe this isn’t cynicism. Maybe it’s what happens when experience forces you to reconsider the rules you were taught—and decide which ones are still worth passing on to the next generation.

SPEAKER_01

Welcome to As the Dinoson's Turn, where we chronicle the adventures of the Dinason family. A seemingly ordinary family from Iowa who decided, hey, you only live once, so let's move to Portugal. And now your hosts, Jason and Tracy Dynason.

SPEAKER_02

Welcome to another episode of As the Dinoson's Turn. It's Jason and Tracy, and also Stan the Dog, if you're watching the video, he wanted to be in on the shot. So this time we wanted to talk about our growing cynicism, I guess, about things. And I don't know. I think we were cynical in a different way when we lived in the United States. And now we've moved. Well, we probably were cynical about the same things. Maybe we just couldn't see it clearly in the US.

SPEAKER_00

And I don't know how to even describe what we're talking about. So bear with us as we go through this.

SPEAKER_02

But cynicism may not be the right word.

SPEAKER_00

I don't know if it is. I think that, you know, growing up, like we're both like at that Gen X millennial area, right? That we believed and were told you go to college, then you get a good job. And it doesn't matter how much debt you take on because you'll get a good job and that'll get paid off. And, you know, then you work hard and all of these things, you can achieve all of the things that are promised to you, right? And I think that we're not alone in that feeling like that that we were sold a crap, and that the last generation that that was actually true for maybe is early Gen X, and but it's really the boomers, and that's it. And the rest of us have gotten the raw end of the deal. I don't know. I think that that's just a widening concern and a feeling worldwide. I'm seeing this worldwide, but I think it's particularly true in some of the structures in the United States, and the way that we structure to limit and then say, well, I mean, just pick your up by your pick yourself up by your bootstraps and grind harder, you know, and it's your fault that you haven't done all of these things when it's the system in and of itself. Does that make sense?

SPEAKER_02

For me, I think it's I remember distinctly being in high school, I don't remember what grade I was in, but the guidance counselor coming in and she literally said, get that degree, get that piece of paper. And I remember she was she was going like this with her heads, get that piece of paper. It doesn't even matter what it's in, if you get that piece of paper, you're set for life. And that was true actually in the 90s.

SPEAKER_00

I think that it was true for a while. And I I think that honestly, it's still true in a lot of respects. So we can't we can't negate the fact that having that piece of paper gives us an amount of privilege in all of this. Like it makes our lives possible, but it doesn't mean that you are set for life, you know, you're set up for a different life.

SPEAKER_02

The days of the stereotypical work for a company for 40 years and get your gold watch and your pension and you ride off into the sunset when you're 62 years old, that maybe that never actually happened.

SPEAKER_00

It did. It just doesn't happen for our generation. I think that the other piece of it is though that like, I mean, we chose careers thinking, okay, this will be the best thing ever. And I am a teacher, I am a mentor, I am an advisor, I went into higher education for a reason. And I thoroughly believed that if you you just jump through the hoops and you play the game and you work on it and the students go first, and I hit that mission, hook, line, and sinker, I was gonna be there and I was gonna be there for 35, 40 years, retire from the institution, had no doubt in my mind. And then the world changed on us too. And so all of the things that were true at one point in time, you realize when you enter into the faculty, they were not true pretty quickly. Like I feel like faculty life changed drastically in like 2007, 2008, the 2008 financial crisis. I just feel like we've never been able to pick things up and move beyond that. And that's for us. Maybe there are people who would even go back to 9-11. I don't know. But we're having these a lot of these conversations now because our eldest, he's going into his last year of secondary school here, which he would have already graduated when we were in the States. He would be going off to university already. We see all of his friends, and we see that going on. And here he's chosen a field, a discipline, a wider area of discipline. He'll have a professional certification. He can go immediately into workforce because he's got all he's got the proven training and like 500 to 600 hours of internship practical work in his field before he even graduates high school because of the field he's chosen. And we're having the conversations of do you want to do university or not? And him saying, if I don't do university, I'm a failure. And I'm like, according to whom? Because that's nothing that we would have ever told you. And he's like, according to everyone. I'm like, oh my God. So I think that we're just kind of stuck in having these same conversations and being like, dude, they lied to us. So we're not gonna lie to you. Maybe this doesn't make sense right now. I don't know, maybe you get an apprenticeship. Maybe you go a different way. You can still get apprenticeships in Europe. Oh my God, we've got a professional certification. Go and get a mentor, work for them for a year or two, see what you think, and then make up your mind. But I feel like we did everything right. We said they said you do this, you said, okay, I'll do this. And they said you do this, and you just keep going. Like you don't know, you just keep going to school. This is how I ended up with PhD. I didn't know, I just kept going, and then I found what I loved and all of these pieces, right? And you don't realize that you're then spending all of your time. You've set yourself up for a certain kind of life, but you're then spending your time trying to make ends meet in a way that you weren't anticipating, right? I think another thing that we were sold or told was that if you achieve something and you get the accolade, that's the important piece, right? And that if somebody else got it, you lost. Right? You were the loser, at least in my house. You didn't win. So you were the loser, you lost. They took it away from you instead of being like, I'm so happy for them, they also deserve this. There's more than one thing to go around. And I really feel that maybe where we live now, there's a different kind of camaraderie. At least even among my students, there's the I'm so excited for you. Like, yes, they're competitive about their grades, but they're like, You got this award and you deserved it. And they don't feel like they lost out on the award. They're happy for their friends. I don't feel like we were I was overallowed to be that growing up. I don't know. What about you?

SPEAKER_02

I've experienced what you read about a lot with the harder you work, the more work you're given, but not necessarily the more money that you're given. I've experienced that. Oh, me too. I've experienced not getting things like promotions because you're too valuable at what you do, that they don't want you to do anything else because you're too good at what you do. Yeah. And now it's like I look at having success in business, but it's like the more money we make, the more we spend, even when we try not to. Yeah. And it's like everybody else gets the money first, and there's nothing left for us. I mean, it is true that the average person has been squeezed the last 50 years or so. It's not that people lived lives of luxury back in the olden days, but it's also true that you didn't have to go to college and you didn't have to do all the bullshit that people do to try to get a job and five different interviews or seven different rounds of interviews or whatever. You could get a job anywhere, and it was enough to at least pay for an apartment and food on the table. And I don't know about you, but I would hear stories of people like, oh yeah, I wanted a new Mustang, so I just worked some overtime or whatever for a few months. I know you're like for you. Bought it with cash. And people could have nice things, even if they didn't live in luxury. I remember Grandpa Dallas, one of his like scorecard things with people was when did they get a color TV? I like so-and-so, he got a color TV in 1965.

SPEAKER_00

I don't know. What I think, quite frankly, is that everybody is feeling the squeeze, and no matter how much money you earn, you never have enough money. And so you also never have enough money for all of the savings in retirement and the things they tell you you should be doing. But it's because the system is rigged. I'm convinced. I'm convinced this is not capitalism, this is post-capitalism. This is like corporate greed at its finest, and yet you see the exact same thing worldwide. Like housing is outrageously expensive. It's expensive here, it's way overpriced what it should be. I think that's true everywhere. Like we just made up this number and said, well, somebody will pay it. And it's like, what, well, who? You know, at some point, who? Like we're having these conversations of okay, so what do you want to do with your life? Let's just be clear the fact that there are sacrifices that come along with that, and we will help you as much as we can, but you're not going into debt for something. I don't feel like we were ever, I definitely was never financially educated, like ever. And I think that I don't even know how to educate my children on finances right now because I can't say it doesn't matter how hard you work, you're never gonna earn enough money to own your own house or any of those things. So good luck.

SPEAKER_02

But I think a lot of people are drawing that conclusion though.

SPEAKER_00

Oh, they definitely are. I mean, look at the look at the statistics. It's crazy. You look at the data. Again, this is my data nerd thing going on, but you look at the data. No human being can earn a living. We know that this generation has it worse than previous generations. And supposedly we had it better than the generation before that, but we're sitting here going, according to whom? Who decided that was better? I don't know. And I think that's what we're struggling with right now in having this conversation. And I as somebody who wants people to be successful and wants to help others, it's just really hard. Because you can't even make it work for yourself sometimes. It's hard to know what to say and what to do. And I know that in our lives, we're not the only parents that are struggling with this right now, having conversations with their kids about these types of things. And then also loving the dream of our youngest wants to be a gamer, wants to be a computer programming person to write games. So should you be looking at design? Should you be looking at storytelling? Should be looking at development if you don't even know how to direct where you put your time and your effort anymore. I feel like we're stuck in a world that's changing too fast.

SPEAKER_02

The rate of change, I mean, the world always has changed, but I think that in the past, generally, you could get into a career and it would still be there in 20 years. But nowadays you get into a career, it might not be there in two weeks.

SPEAKER_00

I feel like the systems that even that we believe truly work will be sacrificed at the altar of corporate and individual greed instead of even thinking about what is best for the collective, because the collective doesn't matter. And that's the part that I'm struggling with.

SPEAKER_02

Well, there you go. Rantings of you're Gen X, and I technically am, although I'm on the border with you're not as young as you think you are.

SPEAKER_00

You are you are Gen X. I was born in the 70s. Give me a second break.

SPEAKER_02

No, 1978, but uh I really was delayed by a year in kindergarten, so I think it was 1979, which is very close to millennials. I always identify more with millennials.

SPEAKER_00

But I do think career-wise, we do identify really well with millennials because you did your second career right in the middle of the millennial uniform entry, and I had such a delay from going to graduate school, I entered into the career world with people who were millennial just starting their careers. And so I we've had this conversation that career-wise, we feel a lot more millennial than Gen X in a lot of cases.

SPEAKER_02

Definitely career-wise, that is for sure.

SPEAKER_00

I feel like it's just a hard world right now, and I do feel like we were, you know, you're promised a lot, or you're told that you you work hard, you can achieve and do anything. That's not true. You can work hard to achieve things or to get your way there. It doesn't mean that the odds fall in your favor. It doesn't mean that you suddenly are gonna just miraculously manifest it and make it happen. It could, it could not. It's luck, too.

SPEAKER_02

And you've been in different industries from what I've been in, but hard work doesn't get you ahead. In fact, the worst workers that I've ever seen tend to be the ones who actually have the run of the place, whether they're the manager or they're just the person or persons who actually everything revolves around. And that's uh uh once upon a time I thought, oh, that's just that place, but then you see it in other places, and then doing what I do as an accountant, you see it with with other workplaces that you observe, and it's like there's something off with what we're told versus what the reality is in so many different ways.

SPEAKER_00

You know, I'd have to say that I was very lucky. I had wonderful colleagues. I though believed in a mission and did all of the things that were asked of me and wanted to lead and be an important and a and care for other people as much as they cared for me and for our students. I wanted to make their lives easier. And in doing so, I found myself trapped in a situation that I didn't know a way out of and couldn't figure out. But I think more than that, there's also the idea of when a system is broken and you're in the middle of the system and you're trying to do what's best for the people that are right in front of you, it's it's exhausting and it's hard. And so I can't even imagine how exhausting it is for my colleagues who are still in it. And I admire them for still being able to do it because being from the outside breaks my heart. And so being inside of it was too devastating for me because we worked hard, we had a really solid department. We were doing all of the things. We were like, if you do this, we're trying to protect your department and you believe it, and you do all the work and you put in all that effort, and yet it doesn't matter. And you realize the institution could really give a shit. It doesn't matter. You're expendable, and it doesn't matter what you contribute. And so I have a huge amount of cynicism and disillusionment. And I think that you probably do too, in a lot of those respects, but it's there is a lot of pain to deal with.

SPEAKER_02

My cynicism anymore. It used to be centered on industries like broadcasting or tax preparation, and now it's more just economic cynicism of like the more you work, the more that other people seem to make money and not you. And that's been my big holdup the last several years is you work hard and you're making more money than ever, but yet there's never enough money. Because everything costs way more, costs way more, and there's other people with their hands on it before us.

SPEAKER_00

I think that we're all having the same conversation worldwide as to what is the answer and what are the conversations we should be having, and how do you address the systems? Because I think when you're talking about economics and the economy itself, it is a system, and we could be making different decisions, and yet we're not making those decisions because we're not thinking about the best for humanity and the collective, and I think that's really hard. We could be making different decisions, we're probably gonna get canceled. That's fine. I was like, whatever. We're gonna I'm already on somebody's list someplace, I'm positive, so that's fine. But I do think that we could be saying no, we could be slowing down AI, we could be letting it collapse and not do anything for it. We could be ensuring that education is funded at the levels as it should be, even the levels it was in the 1980s would make a huge difference in today's dollars. We couldn't be doing all of these things, and yet we make the decision not to because your success and your survival isn't my problem. And I'm so over that. And I see some things that people say are changing, and I'll wait and see because I don't believe it because of everything that we've seen before. I don't know. Wow, we are a downer.

SPEAKER_02

It is a downer episode, isn't it?

SPEAKER_00

Well, but I have to say, like we're having these conversations, these are real conversations. As somebody who thoroughly believes in education, education is the way to change your social status and to change your life. I still would not advocate for somebody to take on the amount of debt that we took on for education. And I don't know how you do it otherwise, honestly. Because even if you say and put money away, you're still at the point where it's never gonna be enough. So you're gonna have to go into some debt. So you have to make those decisions. We need to figure out something that's more upbeat to talk about.

SPEAKER_02

All right.

SPEAKER_00

Welcome to being cynical. I think it's we're more realistic about what we we we don't believe it at base value anymore. Keep fighting the good fight, I guess.

SPEAKER_02

Yeah. We'll make sure our next episode is more upbeat and fun.

SPEAKER_01

You've been listening to As the Dinosons Turn, a podcast presented by Dinoson Media Ventures. Don't forget to like and subscribe and catch us again next time for another episode.