My 20 year career is technical debt or deprecated

It's because conservatism whether big or small c, political or technological, tends to be seen as standing in the way of progress by those who didn't arrive at the same underlying intuitions about the difficulty of tabula rasa development. Because the intuitions are so deep, we barely articulate them and that leads quickly to misunderstandings. Conservatism can easily be perceived as errant obstructionism or even the result of a hidden agenda that stands in the way of a better future, if Great Leaps Forward feel easily achievable. Hence why the OP said when he was younger he saw the past as "evil" - a very common way for young radicals to perceive conservatives.

For example, most companies with large software assets will at some point go through a fight between the old hands and younger devs about whether to do a rewrite in the hot new thing. Which side you're on may appear dominated by age, but it's really more about your intuition about the risks of rewrite projects. That in turn is determined by your experiences of people's ability/inability to fully comprehend complex systems.

Also I didn't try to to be neutral, hence the digs at communism and academia. If I was aiming for karma I'd have left those out. But I'm not.

Because what matters is not the number you can think of, but the scale proportionate to human life / needs.

For somewhat related context: all my life until recently I rented, but now had become a house owner. My strategy with things I bought for daily use was that they were meant to survive until the next move. For many things it wasn't economical to take them with me to the new place. So, for example, I didn't want to buy a "proper" pan / skillet, and was happy with a teflon one just because it would wear off about the time I needed to move again. I could just throw it away and get a new one. Now that I don't intend to move, I'd choose to buy things that last, because cost of moving vs cost of garbage cleanup changed.

Now, when it comes to software, it looks like the industry is overwhelmingly motivated by short-term benefits, where, in principle, it shouldn't have been. And this is the surprising part. Lack of vision / organization leads to the situation where we never even try to make things that last. There are millions of e-commerce Web sites in the world, but they are all trash because nobody could spend enough time and effort to make one that was good (so that others could replicate / build on top of it, and also have a good product). We have the most popular OS, that's absolute garbage, both the core and the utilities around it, which is due to shortsightedness and even unwillingness to plan on the part of the developers. Same thing with programming languages, frameworks etc.

So, looping back to your question: why the magnitude matters? -- what matters is how your own planning compares to the lifespan of your product. Many times in my career I was in the situation where I was building an already broken thing from a design that was known to be broken from the start or very soon afterwards. And that had nothing to do with changing requirements, it had all to do with the rat race of getting a product to the market before someone else does / investor's money dries out. The idea behind "things that last" is that at least at the time you are making them you cannot see how whatever you are making can be done better (as in more reliable / long-lasting).

In the end of the day, what happens now in programming is that things that shouldn't outlive their projected deadlines do, or, predictably, die very fast. But we don't have any section in the industry that builds things to last. We just keep stuffing the attic with worn-out teflon pans.

Compare this to, for example, painters, who despite knowing that most of their work will likely be lost and forgotten, still aspire to produce "immortal" works of art, and if a picture takes a lifespan or more to make, then so be it. (In the past, some works of art were carried out by generations of artists, especially, when it comes to books where scribes were succeeded by their children who'd continue writing the book after their parents death).

Alright, let me be more clear: WSL1 is NOT the POSIX personality of Windows NT. The POSIX personality was very dumb and minimal. WSL1 is NOT that. It is a different thing. And the POSIX personality doesn't even exist anymore.

I’m assuming your paychecks didn’t bounce over those 20 years so who cares?

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