I think Calvin and Hobbes has a more positive outlook on life than Dilbert. To me Calvin and Hobbes mocks things with the attitude of "let's make this better" or "let's explore and find better things" while Dilbert mocks things with the attitude "it'll never get better".
Dilbert has been criticized as not just portraying useless bosses, but also mostly useless employees who never try to improve anything:
Since it’s a normal comic strip, Dilbert can never change substantially. So, what would be worse, a strip where the protagonists are competent and try to change their situation for the better, but always fail, or a comic where most everyone is equally incompetent and you can laugh at them all?
Dilbert has been criticized as not just portraying useless bosses, but also mostly useless employees who never try to improve anything:
https://en.wikipedia.org/wiki/Dilbert#Criticism_and_parody