I went the other way :) I find that I rarely get confused about the types of the things that I'm manipulating, and in practice I find that the problems I have

I went the other way :) I find that I rarely get confused about the types of the things that I'm manipulating, and in practice I find that the problems I have are unexpected behavior from say third-party web APIs, surprising data at system boundaries and so on. Usually I try to mitigate this by introducing a "type system" (or more accurately, declarative data validation enforced at runtime) near the boundary of the application, such as a parser, JSON schema, option parser, etc. The biggest thing I do miss in Python is solid and natural concurrency. Gevent is the closest I've found, but it doesn't play as nicely as I would like.