I also don't understand how one can be in a carefree state of mind while being poor (choosing not to worry about loosing everything), but not be able to attain

I also don't understand how one can be in a carefree state of mind while being poor (choosing not to worry about loosing everything), but not be able to attain that mental state while being wealthy (choosing not to worry about losing a negligible amount). Is the relationship such that the more there is to lose, the easier it is to be unaffected by worry?