Seems like the goal for addressing the first point is to get better at planning and estimating. Learn what you are capable of and then get better.

The second point is based on that Hemingway quote right? “The best way [to write] is always to stop when you are going good and when you know what will happen next. If you do that every day…you will never be stuck.”

I've tried it a few times. I didn't notice much improvement. Maybe it makes most sense when you are working on a problem that excedes your comfort zone.