Is it insensitive to encourage someone who is feeling down to look at the positive aspects of their life?

I have a friend who often comes to me to chat when he’s feeling down. Thing is, this guy is probably the most fortunate person I know. I know it’s not my place to say how anybody should feel, but he is well off, healthy, getting a free ride through school, and has excellent grades and prospects for the future. But he chooses to fixate on the negative aspects of his life. To me that is the definition of pessimism and I try to redirect him to see how many this about his life are good. Is that insensitive? I know even the most fortunate person can still be depressed. I don’t know if he’s clinically depressed or anything, but even so, I know his situation doesn’t make his feelings invalid. I just want to see him appreciate the things he has. Is that bad?