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Perhaps the idea is as follows. While a person must make his hishtadlut, this is merely a prerequisite condition. His initiative, however, is not what leads to the final result. What actually brings about the result is Divine providence.
Yosef exercised his initiative by asking the Sar ha-Mashkim to remember him. But when Yosef specifically instructed him how to use that rememberance by mentioning him to Pharoah, he intimated that it was he in fact who was orchestrating the events that would eventually lead to his freedom.
The Gemara says that a person can remember something to actively pursue it for twelve months. Hence, the Sar ha-Mashkim could have remembered Yosef’s request to act upon it for one year. Had he told Pharoah at the end of the year, Pharoah too could have remembered one year. Hence, at the conclusion of two years, Yosef’s request of the Sar ha-Mashkim could no longer have been effective according to the natural flow of things. This is what God demonstrated to Yosef. Yes, you have to make an effort and take the initiative, but don’t think that this is the ultimate cause of the result. I will get you out of prison just as you thought through the agency of the Sar ha-Mashkim, but only after two years when it will be obvious that your intervention was in fact not the cause.
Many times earning a living is a factor in the decision to make Aliyah. One should remember that while hishtadlut is important and necessary, it must be understood not as a causal factor but only as a condition. Ultimately, God provides a livelihood, whether it be in Chutz la-Aretz or in Eretz Israel. When this is understood, then faith and trust become more of a reality, and the decision to fulfill the mitzva of living in Eretz Israel becomes more easily facilitated.
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Chemdat Yamim Moreshet Shaul: Twin Foundations
Based on Siach Shaul, Pirkei Machshava V’Hadracha p. 690
Based on Siach Shaul, Pirkei Machshava V’Hadracha p. 690

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