Vayigash: Why didn’t Yosef send a letter to Yaakov?

At our Friday night dinner table, my daughter (who is five) asked the question: Why didn’t Yosef send a letter to Yaakov? To let him know he was alive? My daughter’s answer was he was too busy. My son had a different answer, that Yosef did not want to shock his elderly father with the news. To which my daughter insisted that she was right! So my husband tried to explain that there can be multiple answers to a question. But I have the truth!, responded my daughter.

So I did a little research and found two more answers at a site called Shuvu Bonim:

There are several questions we could ask about the matter of Yosef. How is it possible that all those years he did not send any message to his father that he was alive and living in Egypt? Surely he could have done it with ease; he was the servant of Potiphar who was himself a high officer, the chief priest, (Bereishis 41:50, “Potiphera the Kohen of Ohn.” Rashi explains that Potiphera and Potiphar were one and the same, and the Ramban clarifies that, in this context, Kohen signifies a gentile priest). The possibility existed, and especially afterward, when he was made second to the king of Egypt. What would have been the problem to send a letter in the mail or with an Egyptian messenger? Egypt was then the world’s commercial center, and all the surrounding countries did business there, importing and exporting. It should have been no problem at all to find a courier traveling to Canaan.
There were two reasons why Yosef did not do this. Firstly, if Yaakov were to receive a letter that Yosef was alive and would know that the brothers had sold him, he would be angry with the brothers and punish them. With one glance, he could reduce them to a heap of bones. Yosef did not want that they should be punished, especially since the Jewish people still had to emerge from them. Secondly, if the brothers were to hear of his success, and, more particularly, that he had been made a king, they would never come to repent for what they had done. They would never feel any regret, they would say instead, “It was in our merit that he thrived, it was in our merit that he was made a ruler.” The Pirkei D’Rabbi Eliezer says that for forty years he was second to the king, and for another forty years he was the actual king. During his last forty years in Egypt, he was king, and he sought a way the entire time to bring the brothers to regret what they had done. He wanted them to come to true regret, from the depths of their hearts, so that the heavenly accusation against them would be stilled. Without that happening, they could not possibly continue to exist.
This is the way that the Beis HaLevi, who was the father of Rav Chayim Brisker and the grandfather of Rav Yosef Dov, the Brisker Rav, explains the verse, “And Yosef said to his brothers, ‘ I am Yosef. Is my father still alive?’ And they were unable to answer him for they were confounded before him.” (Beis HaLevi, Parshas Vayigash, Bereishis 45:3.) The Midrash comments on this, “Woe to us from the day of judgment! Woe to us from the day of rebuke! The brothers were unable to withstand the rebuke of their adversary.”

My own personal, psychologically-oriented explanation is Yosef had his own fears. He probably had a block on reconnecting with his family members. So in some ways, my daughter is right: he kept himself busy in order to avoid dealing with the deep-down pain he must have felt by his brothers’ rejection.