Never Say, “I Should Have”


Someone who truly trusts Hashem does not live in the past, regretting decisions he had already made. We so often hear people lamenting, “I should have done this” or “I should have done that.” This is a dreadful curse – feeling distress and anxious over past mistakes. The Torah in Parashat Ki Tavo describes 98 curses, Heaven forbid, one of which is sheedafon, which refers to a kind of damaging wind that ruins vegetation. But it has been pointed out that the word sheedafon sounds like “should’ve.” There is a curse that we might call the “should’ve syndrome,” where people are constantly thinking of what they “should’ve” done. A person wants to sell his home, puts it on the market for $1 million, and receives an offer of $900,000, which he refuses. Three years later, when the house is not sold, he goes around thinking and saying, I should’ve sold it. A person goes to a doctor for treatment which is unsuccessful, and he thinks to himself, I should’ve gone to a different doctor.

This attitude is incorrect. If a person puts in his hishtadlut (effort), and made what appeared to him as the best decision at the time, then the reason why it did not work out as he wanted is because Hashem, in His infinite wisdom and kindness, did not want it to work out that way. Even if in the end it becomes clear that he could have made a much better decision, it is min haShamayim; the wrong decision was made because that is what Hashem determined would be best. He did not allow the better option to enter the person’s mind, because He knows what is best.

The Gemara (Berachot 32b) teaches, “Everything is in Hashem’s hands except for the fear of Hashem.” This means that Hashem gives us free will to decide between right and wrong, between doing mitzvot and aveirot, but that is all. All our other decisions are made by Him. The Sfat Emet comments that Hashem is involved even in our thought processes, and thus if he wants us to be in a certain place at a certain time for whatever reason, He will put the idea in our mind to get us there.

A woman recently told me that she was in Manhattan for a business meeting, and after the meeting she decided she wanted to go eat lunch. She passed a pizza shop, but decided she was not in the mood for pizza. She then passed a sushi restaurant, but did not feel like eating sushi. She was thinking of whether she wanted to eat meat for lunch, and decided she was not in the mood for meat. Then, suddenly, she felt a craving for a chicken salad. She headed over to Kosher Delight, and as soon as she walked in, she saw her best friend, who rarely comes to

Manhattan. She ran over to her friend to say hello and to ask what she was doing there, but she noticed that her friend was reciting Tehillim.

As soon as she finished reciting Tehillim, the friend turned to the woman, said hello, and explained that she was praying to Hashem to send her a ride to Brooklyn, because she did not want to take the train. As she was praying, her friend walked in. Hashem sent her to Kosher Delight. He is involved even in our thought process.

And so, the person who has firm faith in Hashem knows that once something happens, it is exactly what Hashem wanted to happen. As long as we do our hishtadlut, and try our hardest, doing what we genuinely feel is correct, we should not think twice about it. Once it is done, we believe with complete faith that the outcome was Hashem’s will. So, unless the decision has to do with mitzvot or aveirot, we should never say, “I should’ve,” and we should never second-guess ourselves. Everything that happens is precisely what is supposed to happen.