Self doubting effects are for weak riders. If he fails then wusses out, then he deserves to fail. But this guy doesn't sound like a wuss to me!
Now if he's smart, evena fail will not bring out self doubting effects. Its called experience and learning from mistakes. Then he must go back and look at the things he did wrong as far as (mentioned by sstorkel), diet, drink, fit etc.
There is no losing in doing a 60 now. IF for some reason he fails, then he counts it towards his ramping program. IF he makes it, then he betters his habits on the ride looking for better results. A few days of recoup rides. Then the following week he drops back a few miles then begins the ramping process one again with confidence and experience!
I tellya, I've done about 35 centuries and ther have been about 4 that I got to 80 miles and thought, I better slow down or back off. It's not a negative self doubting issue, it's called a wise move that comes with experience!
Out of curiosity, have you had any century fails or completed any century rides that left you feeling negative self doubting effects?