Photo Credit: Jewish Press

Brian (not his real name) was a partner at a major investment firm and known to generate amazing gains for his clients. As a result, he achieved worldwide fame, and CEOs of major corporations hoped to have their accounts managed by him. When he interviewed potential clients before taking them on, he would say:

“The only way I can work with you is if you promise me one thing: Never look back.


“If I buy a stock for $10 and sell it when it shoots to $15, great! You made money. If it continues to rise to $20, though, don’t say, ‘We should have held on!’ You can’t care what happens afterwards. You have to be happy with the profit and continue to look forward, not backwards.

“I understand regret is natural. But imagine someone gives you $100; would you turn to him and say, ‘Why didn’t you give me $150?’ No, you would be grateful. If you agree to this condition, we can have a business relationship.”

The words by which this financial advisor operated reflect what Hashem expects from us as well. To maintain a joyous connection with Hashem, we need to learn to erase could’ve, should’ve, would’ve from our thoughts. The birth of Moshe Rabbeinu illustrates this point beautifully.

Pharaoh had decreed that every Jewish baby boy should be thrown into the Nile, so Yocheved hid her newborn, Moshe. The Torah says, “The woman [Yocheved] conceived and gave birth to a son. She saw that he was good and she hid him for three months” (Shemot 2:2).

After three months, she could no longer safely hide him, so she placed him in the Nile River. The Gemara (Sotah 12) states, “Immediately after Moshe was placed in the river, Pharaoh’s decree ended.”

Pharaoh initially made this decree because his astrologers told him the Jews’ savior would be born that day. Once the astrologers realized the savior had been placed in the Nile River, they assumed he had drowned, so the decree was nullified (Shemos Rabba 1:21). The end. Gone as quickly as it came.

Rav Yankel Kozheilik, zt”l, said that Yocheved could have thought, “We just missed the cutoff! If only we had waited, our baby could still be with us.” Yet, according to the Gemara, Yocheved’s act caused the end of the decree!

Rabbi Kozheilik explained that this is how life often works. A person may think, “If only there were no traffic, I would have arrived at the meeting earlier and could have spoken to the right person.” But the truth is, you were delayed because you weren’t meant to meet that person.

Hashem orchestrates every detail of His world; He has an intricate, puzzle-like plan. And just like Yocheved didn’t regret her act, so too we cannot obsess over our past decisions. Whatever happened was from Hashem, and could not have been avoided.

Rav Leib’ke Gloiberman was faced with health problems in his later years, and one doctor recommended that his leg be amputated. Rabbi Gloiberman consulted with many physicians and ultimately decided to proceed. Some time after the surgery, the doctor said, “We now realize that we probably could have avoided amputating your leg.”

When Rabbi Gloiberman heard this remark, he dismissed it entirely! Waving his hands in the air, he exclaimed, “Ehh! These ears heard from the heilige Yenuka [Rav Yisroel Perlow, the “Yenuka of Karlin-Stolin”] that ‘would’ve, could’ve, should’ve’ is apikorsus!”

He continued, “Perhaps in the medical books they will record that it wasn’t necessary to amputate. However, this leg had to come off. How do I know? Because they amputated it! If it came off, that’s what Hashem wanted!”

The Gemara (Nedarim 9) says, “Reshaim are full of regrets.” Rav Pinchos Koritzer asks, “If they regret their actions, why are they reshaim? They should be praised for regretting their actions and trying to repent!” He explains that the Gemara isn’t referring to wicked people regretting their sins. Rather, it’s referring to a regular person who thinks, “Had I gone there, something better could have happened.” Such thinking is wickedness.

How many times have we thought:

* If only I had met this guy at a later stage in life, it could have worked out.

* I should have purchased that property a few years ago when it was going for much less.

* I shouldn’t have had fleishigs for lunch because now I can’t have ice cream!

Brian, the investment firm partner with whom we began this article, was once offered the exclusive American rights to importing Perrier water. This opportunity was presented to him at a time when bottled water had never been sold in this country, so he declined it, thinking, “There’s no way anyone will pay for bottled water. Water is free!”

Imagine the wealth he would have accumulated had he accepted the opportunity. But when asked if he ever regretted his decision, he responded, “Never. I don’t look back. The Perrier opportunity wasn’t meant for me. Something else was meant for me. I was meant to be blessed financially, and therefore it came through another avenue.”

Forget could’ve, should’ve, would’ve! When we look back and feel regret, we become stuck thinking about something that wasn’t meant to be. But when we close the door and move forward, another opportunity – the right one – opens in front of us.


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Sarah Pachter is a motivational speaker, columnist, kallah teacher, dating coach, and the author of "Is it Ever Enough?" (published by Feldheim) and "Small Choices Big Changes" (published by Targum Press). She lives in Los Angeles with her husband and five children.