My example explicitly assumes them equal because it's trying to isolate and illustrate the factor of memory context.
In real life, options are never really equal, but you also never have enough information to sort or compare them properly. Whatever path you choose is eventually judgment call.
I like to imagine that decision process, and every decision process like this: Inside of my mind there's a painter, painting a picture for me. My cognitive skills are his painting skills. Health of my mind is health of his hands and his eyes. The information that I have is colors and shapes that he can use. He paints a picture, then I look at it and decide, entirely on gut feeling that I get from the picture.
Any decision that I make, and any action that I do, can only ever activated using feelings. Rationality is essential and possible, but rationality is for the painting. The action must come from the feeling.
Pictures are painted over pictures every second, and by the time we reach adult age, there are thousands if not millions of pictures painted over and over. However, some pictures are bigger than others so they rarely, or never get painted over. They can stay there for years on end. Often, pictures painted by much younger painter with far less skills and information will stay. Some of them are happy and fascinated with the beauty of the world, sometimes, some of the old pictures will be unsettling, like the kinds of pictures abused children would draw. They can stay there, lurking in the background, making us feeling like we're watched, like we owe them something.
It's these old pictures that can alter our feelings in a way that does not seem rational--why do I feel my time is 99% wasted could be example of that--you feel it because it's the feeling you get from some of the many old pictures in the corners of the canvas. There's nothing wrong with you: the feeling is true to the picture--any of us would feel the same from the same canvas. There's no reason to blame yourself.
There's also nothing wrong with the pictures, and nothing wrong with the little painter that painted them years ago. These were his shapes, colors and his skills. So there's also no reason to blame the painter. After all, he's frozen in time, there's no point in blaming a memory, memories cannot change.
You can, in some meaning, however, connect to with younger painter in terms of understanding him and his situation a bit better and seeing which pictures are still relevant to you. Some of them will, for some of them you will already know better. Then, maybe you can work with the current painter and get him to re-paint some of the old pictures or at least mark them as the historical artifacts that they are. It's all hard work but you're not alone.
To some extent, maintaining the paintings and teaching the painter is the point of life. We were never meant to be alone in that.