Should one do actions that prepare for the eventuality of a negative outcome? Such as if one is sick, should he write a will and prepare his family for the eventuality of death?

Seemingly, there is no contradiction in one’s Bitachon if he takes steps which prepare for the eventuality of a negative outcome, the same way that one’s trust in the coming of Moshiach should not prevent him from investing energy in matters which will not be relevant when the Moashiach comes. At the same time that one has absolute faith in G-d that he will save him, he should also make necessary preparations for a potential negative outcome. Thus, if a person is suffering from a deathly illness r”l, him and his relatives should not ignore the possibility of death occurring and they should do everything necessary to prepare for the eventuality of death, such as to write a will and instruct one’s family and the like with both physical and spiritual parting messages, as did both Yitzchak and Yaakov our forefathers. In the case of young children who may potentially become orphans G-d forbid, the orphans should be mentally prepared as much as possible, together with them being strengthened to have absolute faith. This type of behavior was vividly seen to be followed by the Alter Rebbe, who a mere day before his release from prison sent a letter to his family in which he prepared them for the possibility of his death, if the will of G-d was for him not to survive G-d forbid.[1] Perhaps, one can suggest, that this preparation is part of the steps to be taken before one reaches total trust in G-d, and the realization of the seriousness of his predicament to the point that he must prepare for its negative outcome, may be the motivating factor to propel him to rehabilitate his relationship with G-d to the point of absolute trust. May Hashem save all of us from any such predicaments!

______________________________________

[1] See Igros Kodesh Admur Hazakein letter 127