I have had a number of times where static typing would have saved me a lot of time in both Python and Javascript. I have a recursive-descent parser for a non-trivial language in Python, so when you pass something incorrect down in the bottom it bubbles up and fails up the stack and a bunch of calls later. But if I'd had static typing, the compiler would have caught it immediately. Similar story for a 3D model generator in Python. I've wasted enough time on stuff like this that then next Python project I do that I think will be over 1000 lines long I'm going to write in some statically-typed language.