So, I spoke with HaRav Gamliel Rabinovitz shlit"a yesterday regarding the question I had about Yosef's hishtadlus in relying on the wine steward (see here).
Rav Gamliel explained to me, in addition to what I said, that every person is obligated to do his hishtadlus. The thing is, every person has a different amount of hishtadlus he is obligated in, depending on where he is holding in life (emunah, bitachin, yirat shamayim, etc..).
Yosef was already at the point where he was a great man and at a very high level of yirat shamayim. For Yosef, relying on the wine steward was an inappropriate level of hishtadlus and that is why he had to sit in jail for those extra two years.
That means we are all obligated to evaluate our positions in life and know who we are and what we are, and act accordingly.