You get used to it somehow. I did C and Java for about 10 years before Python. My first exposure to Python was a Computational Physics class and it was maddening not knowing what types went where. Eventually you realize it doesn't really matter as long as you're disciplined and rely on others who are disciplined enough to document their code well. I haven't had the chance to use mypy in the 7 years I've been using Python (across 3 industries; medical devices, scientific devices, and web) but I would be surprised if it significantly reduced the number of bugs I've seen in practice.