How picky can you be?

How one should live his/her life? Should one do what he/she likes to do? Or one should just take whatever presented in front of him/her? The more affluent we are, the higher is our expectation. Older generation said don't be so picky...It's not easy to get what you want...Well, my argument is if you just take whatever offered to you, you probably won't know how much higher you can aim...Is money the main issue in life? Maybe it's a stupid question to ask, but I think as long as we work and live happily, money will come by itself.