Glad I can help. This is another reason why these virtual environments are really useful! I have one environment for sage which I never try to update since I know that everything works. Separately, I have my "main" environment that I update regularly, which will occasionally break things. I broke ipython in that environment and then stumbled on
https://github.com/ipython/ipython/issues/12740 which tracks this problem.
You can also feel free to experiment without fear of breaking things using conda. For example, I see that you have sage installed with python 3.8. If you wanted to try sage with python 3.9 without any fear you could do something like
conda create -n sage_python3.9 sage=9.2 python=3.9 -c conda-forge
and then you would have a new environment with sage 9.2 and python 3.9.
Given how often Mac's new operating systems break everything, it's kind of amazing that conda has been so stable. A lot of credit goes to Isuru Fernando and the work that he puts in on maintaining sage on conda forge.