And no, talking to the rubber ducky doesn't help.
In the beginning of my career I was much more diligent about this (but I also didn't write as readable code, so it was more necessary); the exercise was simple:
When I hit the stupid part of the day (the end of the day), I go back over code. When I don't understand something, I write down something about my confusion. In the morning, when I'm back to being smart, I convert all the confusion to comments and/or better code.
Anything you talk to the rubber ducky about probably deserves writing down.
Yes, unless it is single-use code. Otherwise, if the person is only developing for himself, he can choose whether or not to write any documentation, but if he is sensible, he will write something.
It is moot anyway, as he was not supposed to be a solo developer.
Now you expect a solo person to document?