For me, it is not about money nearly as much as it is about time and the people I associate with. When I was in college, I didn't have any money ever like most students. Yet, I was more relaxed, comfortable, and genuinely had more fun regularly than ever before. I believe this was true mostly because of the people I lived around and the amount of free time I had.
Now that I am in the "real world", I make plenty of money to make me happy and comfortable but I am not as happy as I was in college because my friends and I just don't have the kind of time we used to have. Regardless, I am not unhappy either and life has been very good to me. I wouldn't change it for anything.
It wasn't always like that though. When I first got out of college, I had some jobs where I was over worked like hell (happens a lot these days being in the software development industry). I really was disliking life for the most part. I eventually found myself a nice and cozy government job which is almost stress free, I make plenty of money, benefits are tremendous, and I have tons of free time. I am so much happier now.
So, I basically concluded that being comfortable was all about being rich in time and the freedom to use it than it was about money. Of course, money doesn't hurt either hehe.