Personally, I agree with your point of view. There is, however, something to be said for people that never settle and by force of will reshape the world around them to conform to their expectations.
Steve Jobs is great an inspiring, because he did X and Y and Z and never compromised his standards.
You know what? You happen to know of Steve Jobs because everything worked out well for him.
There may very well be 20,000 other people who refused to compromise their standards...and perhaps that strategy really sucks and the other 20,000 of them went bankrupt and are working at used car lots now.
"Never settling" sounds great.
I'm not 100% convinced that it is.
But... you have to be careful to stay in reality. Otherwise you end up tilting at the mills.
If by force of will I wanted to work at Google for example, I would take steps to improve my chances of making that happen. This story is not about force of will at all, but someone with low self discipline and possibly depressed (clinical depression could be a factor here and he should look into it).
He complains about lack of something to do. There is plenty to do starting with making a schedule listing things to learn for the day that will improve his chances getting the job he wants. I'm sure potential employers are looking at him asking the same questions people here are asking. You've been unemployed for 2 years and have learned what?
Two years of unemployment should be enough to indicate that force of will sometimes isn't enough.
If you refuse to try a strategy for 2 years, that's not evidence the strategy won't work.
What he should be trying is a new strategy, not pouring more force of will into this one.