How does Jim feel about the way Tiny has lived? How can you tell?

Tiny Soderball does not seem particularly happy or content when Jim meets her. Jim senses that all she cares about now is making money, and though he does not fault her for this, pities her for her lack of feeling and personality. To Jim, Tiny does not seem like a complete, engaging person, and her monetary success is thereby subtly undermined.

Jim doesn't seem to think that Tiny has lived ultimately successful, rich life. Tiny is close to only two people and is jaded and bored with life. She does not have a life that Jim is particularly envious of. In order to be truly successful, a person needs something else, and at this point Jim does not know what that is.