Jerry always expects the worse to happen and appears to doubt that he will reach his goals. Jerry is experiencing:

Jerry is experiencing pessimism.

Pessimism is a tendency to think in negative terms. A pessimistic person is always thinking about the worst scenario. He/she always has negative answers and perspectives of life. It is very hard for them to concentrate in positive situations, even when the odds are on his side.

Psychologist believe that pessimism could be a trait in the personality of an individual, probably influenced partially by genetics.