Our Gemara on Amud Aleph references the metaphysical idea that one does not do actions (or even say things) that hasten painful or disturbing events. Thus the Gemara later on 75b says if one is giving a Get on a stipulation that he dies (so as to protect his wife from falling to Yibum), the stipulations should reference “if I live” first, and then mention the other conditional clause about what happens should he die. This is so as not to hasten unfortunate events. There is a similar idea known as, “Al tiftach peh le-Satan”, which literally means, “do not give Satan (the accuser) an opening argument”, i.e., do not speak evil of yourself, as this will allow Satan to contend that you deserve some kind of suffering (see Kesuvos 8b),

There is a question brought down in Sefer Chaye Nefesh (vol 6) about if taking out a life insurance policy is considered making an evil portent, as of course it is anticipating one’s demise. He answers it is not, based on prior responsa such as Lechem Shlomo (II:YD 67) who states that since it is to bring about a benefit, i.e., supporting his wife and children, it is not considered Al Iftach Peh LeSatan. He also quotes a responsa of the Rivash (114) who uses a similar rationale to permit buying a burial plot.

While we are on the topic of insurance, there is a famous Teshuva of Rav Moshe (OC II:111)  where he rules that life insurance is not a lack of faith in God. Interestingly, it is said in the name of the Shinever Rebbe (Rabbi Yechezkel Shraga Halberstam 1813–1898) that to the contrary, life insurance is a segulah for long life. His reasoning is as follows: Since the financiers of life insurance companies are clearly wealthy and successful, they must have mazal in regard to maintaining their fortune. Therefore, this should increase the likelihood of continuing to live. It is kind of like the adage of taking an umbrella so that it won’t rain.

However, the Chofetz Chaim was not a fan of insurance. He believed that one must solely trust in God. There is an amazing story brought down in his biography written by his son Aryeh Leib (Toldos Vkoros Chayyav, pp 90-95) that speaks to this issue, and to the generational differences between them. Once there was a terrible fire that burned down half the town, but miraculously stopped by the Chofetz Chaim’s home. Their home became a refugee center to the extent that they were even recognized and honored by the secular municipality. One and a half years later, the other half of the town burned down, this time, including the Chofetz Chaim’s home. The Chofetz Chaim felt that it was the kindness of God, who delayed the catastrophe by breaking it up into two events instead of one.

Now this is where the story gets interesting. After the first fire, his son wanted to buy fire insurance. The Chofetz Chaim was against this idea, considering it a lack of faith in God. However, his son secretly bought life insurance anyway. Ultimately he saved the day and they were able to rebuild their home. In fact, while rebuilding, they also put down a wood floor (instead of a dirt floor) to please the Rebbetzin. His son tells us that this also was something that his father was against. He felt, “Now that we have a wood floor, we are going to have to spend more time and money maintaining it.” As it says in Pirke Avos (2:7) “More possessions, more worries“. But, they did buy life insurance and they did get a wood floor. And so, we see the difference between generations in terms of bitachon and observance.