I can't imagine how much of a breath of fresh air Python / Java must have been if you were used to write typical business crud apps (and server software) in C/C++ (with no sanitizers / modern tooling to speak of).

It wasn’t. Java was very different from its current state before roughly Java 5. It felt like a downgrade from C++ to me at the time. C++ had templates and RAII and smart pointers, all of which Java lacked (and in some respects still lacks today). Not having something like the C preprocessor was quite annoying. Java performance wasn’t great. Tooling was better in some ways, worse in others. Linters did exist in C/C++, as did debug versions of libraries. You could load a crash dump into a debugger and could often get a pretty good picture of what went wrong. While Java certainly became preferable for business code, it wasn’t a sudden breath of fresh air, it was trade-offs that gradually became more favorable to it over the years.

I used to joke that using something like Python or C# felt like "programming with oven mitts". I never felt like I had any control. But that eventually morphed into "Well, I don't need that control and can focus on other things."

I spent the last few months building a toy LLM from scratch. I can't believe that within my lifetime I've gone from using punch cards to arguing with Claude when it does something ridiculous.