I worked at a Python shop for a bit. I spent more time than I wish to admit trying to make all of my Python behave like TypeScript (adding typings, etc.).

Ditto. Python(3.13) types are so crudimentary that it becomes a Sisyphian struggle. Library type support is patchy at best. **kwargs is an abomination. Python is incredibly slow. Async code and anonymous functions are awkward and verbose. Hell, Python is verbose.[1] I could complain endlessly, but I'm mainly just disappointed in how little has changed since I last professionally wrote Python. The biggest benefits were basically a) familiarity, and b) powerful stats/ML libs.

I hadn't seen analogs of `AttributeError`s and `TypeError`s for years, until revisiting Python and remembering that those are still unsolved issues outside of TypeScript. Ugh.

[1] https://news.ycombinator.com/item?id=36407112

Would a python developer feel the same in reverse?

If they'd go to JavaScript, they'd feel a sense of unfamiliarity similar to what JS developers going to Python would feel.

But the Python equivalent of TypeScript is mypy, and I don't think it's controversial to say (even among Python developers) that it's way behind TypeScript, generally.

Python now has type hints which makes it closer to typescript, and easier to code in.