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We should all listen to guys like your boss. Circumstances have changed a bit but their beliefs are generally directionally correct and they have some great lessons to teach.
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I’m directly between his age and the age of the people he criticizes. He has absolutely no understanding of what challenges young people face. His path to stability has vanished. There’s no apprenticeship program in that union anymore and in the ones that are, the percentage of your living expenses to your income is incomparably higher. The younger people work more hours than he did at their age and have a hell of a lot less to show for it because it buys a hell of a lot less. Since wealth compounds, this is not merely a temporary setback — it’s a completely different arc of progress. Many have replaced pensions with riskier and less stable 401ks. He has no idea what he’s talking about. His formula for success in life basically starts with “begin an industrial career just before the peak of the golden age of US manufacturing in a heavily industrialized area in the golden age of organized labor.”
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In South Korea everyone was recently using 3x leverage on the stock market—which mostly consists of just 2 companies, so concentrated that American institutions aren't allowed to call their index funds diversified—because you have nothing to lose by losing 200% of your money. Which did happen last week as the market crashed. Those people are no worse off for losing 200% of their life savings, because they are already at zero if they don't literally win the lottery—life savings weren't enough to be net positive.
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I think it’s pretty hard for people that came up in the 70s and 80s who are ending their careers to wrap their heads around how shit it is to try starting a career/life right now. Even when people outright tell them, they assume those people are exaggerating or making excuses for not challenging themselves. Back in those days there was always some other route. The entire lower-end of the job market, including just about anything entry-level, is so deliberately extractive now that, by design, you just ‘can’t’ get ahead. That’s where the financial nihilism comes in.
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I feel like they were more confident back then. They knew if they followed a certain path they were likely to succeed. Now it's all murky and it's obvious that most paths lead to failure, but it's not obvious which ones don't.
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Well imagine having the entire first like decade of your career happen before the Reagan era blessed the relentless pursuit of profit at the expense of anyone, even if they were core parts of your company? Before Private equity, rampant off-shoring, etc. etc. etc. Even in the nineties people were saying things like “don’t switch jobs too often because it will make you look disloyal.” Well now, in many industries, if you have the same job for 5 years people think you’re just unmotivated. Considering how little employers are willing to invest in employees compared to recruiting shiny new ones, it makes sense.
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It's true, but part of the problem is that there is an oversupply of people seeking high-skill jobs before they have had the time to actually build those skills. Whereas if you need to a guy to haul lumber around, and there's a guy standing in front of your lumber saying "I can do that", he can probably do it right now and you pay him for it.

There are still jobs like that, but living standards have increased so much that they aren't considered worth taking when you can hold out longer for better ones, to the point that it's considered like a "boomerism" to suggest doing jobs that people in other countries are happy to take to live at a 1970's standard of living.

Even in the US there are seasonal blue collar jobs like that. Youth generally last until 25 or so now though, and that's partly just a skill issue/matter of mindset, because it didn't sound weird for a 20 year old to work in a factory or on a boat back then like it does now.

IMO the giant difference between now and then is the massive gap in income/wealth between people just starting out or working 1970's style jobs, and jobs with global reach and high leverage (ie the most capable produce 2-100+ times the value, but the average person produces nothing of value or negative value). There are WAY more opportunities to benefit from that now than there were in the 70's. I think that's what causes most of the angst tbh, that there is so much more opportunity cost and variance in outcomes now because of global trade/technology, if you just want to work to live you're not going to the same results as people who live to work, or people living places where they literally have to "work to live".

To be honest I don't think the boomer mindset of just working to live and play with your expensive toys was ever a very good one, because it led to the consumerism that makes people think they need $10M to retire or seek $200k jobs right out of college without actually wanting to do those things enough to achieve them (and not needing them anyway)

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That we should act like "self made men" when in reality it took entire multiple lifetimes worth of effort where people in power were finally allowed to create a society where a common trades worker could enjoy an upper middle class lifestyle?

Hard pass, I'd rather talk to his union rep.

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The union rep is, indeed, a good dude!
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