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Putting Dinah's box situation aside, Yaakov wasn't punished for taking multiple measures in preparation of his confrontation with Esav. He should have just prayed, but he also sent gifts, separated his camps, etc..

One answer to this is that we learn from here that hishtadlut is important alongside prayer. So then, why did Yosef get punished for asking the winemaker to remember him? (According to Rashi)

EDIT: Also

I don't think a commentator says that Yaakov was successful in his meeting with Esav due to his hishtadlut, but nobody, seemingly, says he was wrong for his hishtadlut, and so it can be figured that his hishtadlut was a good thing. I think it's the Ramban that says that, from Yaakov's hishtadlut, we learn how to deal with our enemies and not just to rely on righteousness or miracles.

Also, could something be said for Yaakov's formal prayer in the midst of him preparing to meet Esav? It does not seem that Yosef formally prayed to Hash-m in addition to telling the winemaker not to forget him, unless I am missing something?

Putting Dinah's box situation aside, Yaakov wasn't punished for taking multiple measures in preparation of his confrontation with Esav. He should have just prayed, but he also sent gifts, separated his camps, etc..

One answer to this is that we learn from here that hishtadlut is important alongside prayer. So then, why did Yosef get punished for asking the winemaker to remember him? (According to Rashi)

EDIT: Also, could something be said for Yaakov's formal prayer in the midst of him preparing to meet Esav? It does not seem that Yosef formally prayed to Hash-m in addition to telling the winemaker not to forget him, unless I am missing something?

Putting Dinah's box situation aside, Yaakov wasn't punished for taking multiple measures in preparation of his confrontation with Esav. He should have just prayed, but he also sent gifts, separated his camps, etc..

One answer to this is that we learn from here that hishtadlut is important alongside prayer. So then, why did Yosef get punished for asking the winemaker to remember him? (According to Rashi)

EDIT:

I don't think a commentator says that Yaakov was successful in his meeting with Esav due to his hishtadlut, but nobody, seemingly, says he was wrong for his hishtadlut, and so it can be figured that his hishtadlut was a good thing. I think it's the Ramban that says that, from Yaakov's hishtadlut, we learn how to deal with our enemies and not just to rely on righteousness or miracles.

Also, could something be said for Yaakov's formal prayer in the midst of him preparing to meet Esav? It does not seem that Yosef formally prayed to Hash-m in addition to telling the winemaker not to forget him, unless I am missing something?

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Putting Dinah's box situation aside, Yaakov wasn't punished for taking multiple measures in preparation of his confrontation with Esav. He should have just prayed, but he also sent gifts, separated his camps, etc..

One answer to this is that we learn from here that hishtadlut is important alongside prayer. So then, why did Yosef get punished for asking the winemaker to remember him? (According to Rashi)

EDIT: Also, could something be said for Yaakov's formal prayer in the midst of him preparing to meet Esav? It does not seem that Yosef formally prayed to Hash-m in addition to telling the winemaker not to forget him, unless I am missing something?

Putting Dinah's box situation aside, Yaakov wasn't punished for taking multiple measures in preparation of his confrontation with Esav. He should have just prayed, but he also sent gifts, separated his camps, etc..

One answer to this is that we learn from here that hishtadlut is important alongside prayer. So then, why did Yosef get punished for asking the winemaker to remember him? (According to Rashi)

Putting Dinah's box situation aside, Yaakov wasn't punished for taking multiple measures in preparation of his confrontation with Esav. He should have just prayed, but he also sent gifts, separated his camps, etc..

One answer to this is that we learn from here that hishtadlut is important alongside prayer. So then, why did Yosef get punished for asking the winemaker to remember him? (According to Rashi)

EDIT: Also, could something be said for Yaakov's formal prayer in the midst of him preparing to meet Esav? It does not seem that Yosef formally prayed to Hash-m in addition to telling the winemaker not to forget him, unless I am missing something?

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Putting Dinah's box situation aside, Yaakov wasn't punished for taking multiple measures in preparation of his confrontation with Esav. He should have just prayed, but he also sent gifts, separated his camps, etc..

One answer to this is that we learn from here that hishtadlut is important alongside prayer. So then, why did Yosef get punished for asking the winemaker to remember him? (According to Rashi)

Putting Dinah's box situation aside, Yaakov wasn't punished for taking multiple measures in preparation of his confrontation with Esav. He should have just prayed, but he also sent gifts, separated his camps, etc..

One answer to this is that we learn from here that hishtadlut is important alongside prayer. So then, why did Yosef get punished for asking the winemaker to remember him?

Putting Dinah's box situation aside, Yaakov wasn't punished for taking multiple measures in preparation of his confrontation with Esav. He should have just prayed, but he also sent gifts, separated his camps, etc..

One answer to this is that we learn from here that hishtadlut is important alongside prayer. So then, why did Yosef get punished for asking the winemaker to remember him? (According to Rashi)

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