I started doing this about a year ago and it has made me a better Python developer. Getting into the habit of always writing a type annotation was hard at first, but you quickly get used to it. It helps if you configure mypy to complain at you if the annotations are missing.

You'll have a much better experience in an ecosystem where typing is the widespread expectation, IME.

Try an ML-family language if you haven't already - I find they combine the best parts of something like Python and something like Java. There was a post pushing F# earlier today.

If you're starting a new project you can force yourself by running mypy's strict mode in CI.