You learn by actual experience
When I first started riding just enough where I was barely comfortable with highway riding and riding at night, I decided to go out for a joy ride one late afternoon. I kept riding on this one highway just for that curiosity to see what was out in an area I've never been to. One of the reasons that makes joy riding joyful.
Thinking that the highway I was on would be straight as it was when I started, I continued on about 40 miles and found that all of a sudden, I'm in the mountains riding all these twisty roads. I never experienced riding on this many turns at one time. I was overwelmed, but kept patient and just went with my rider training to carefuly ride all the curves. The sun was starting to go down and the rock formations around me were a beautiful reddish-orange from the sunset. I don't know if the beauty of it made me more relaxed, but it sure wasn't something I saw everyday.
I probably went through another 25-30 miles of twisty roads when I got to a small town.
I refueled and though I better go back home. It is now dark outside. Now I have to go back through all those same twisting roads in the darkness. I followed a semi-truck and other vehicles back and used them and their headlights on the road ahead as a guide.
Needless to say, I made it back home okay. But after all that, I was now more comfortable and more skilled with riding on multiple turns and riding at night than I ever was.