The Medrash states (Bereishis Rabbah 89:3): “’Praiseworthy is the man who places his trust in Hashem. (Tehillim 40)’ This refers to Yosef. ‘And he does not turn to the haughty.’ Because he told the minister of drink twice to remember him, two years were added to his sentence.”
This Medrash is confusing. It first refers to Yosef as someone who placed his trust solely in Hashem but then says that he is criticized for placing trust in the minister of drink. We may futher ask why it was considered improper for Yosef to ask the minister to remember him. Isn’t a person commanded to do his hishtadlus to save himself from a difficulty?
Sefer Kometz Haminchah answers that although the hishtadlus of merely asking the minister to remember him would have been acceptable for most people, Yosef was such a tzadik that he was expected to live on the higher level of not putting forth any physical efforts to help himself. Therefore, even though he had full bitachon in Hashem, he was punished for engaging in any form of hishtadlus.
Accordingly, the Medrash is saying that Yosef was on the highest level of trusting only in Hashem, which is why he was punished for asking the minister to remember him.
