Jacob had to take care of the burial of Deborah, his mother Rebekah's nurse, without seeing his mother (35:8). God did not allow Jacob to see his mother, but he had to take care of the funeral of his mother's nurse. This, no doubt, was a suffering to him.
Jacob later had to suffer the death of Rachel (35:16-20). Rachel was the wife of his choice, the one whom he loved the most. She died while she was delivering Benjamin. While she was dying, she called his name Benoni, which means the son of my sorrow. But Jacob immediately called him Benjamin, which means the son of the right hand. This became a prophecy in typology. Christ in His incarnation, on the one hand, was the Son of sorrows from His birth through His human life on the earth (Isa. 53:3). Then through His resurrection and in His ascension, He became the Son of the right hand of God. Thus, "from Benoni to Benjamin" is the story of Christ accomplishing His redemption from His incarnation through His ascension. Benjamin represents God's accomplishment of His complete redemption through Christ, first as a Man of sorrows and second as the One at the right hand of God.
Jacob had to suffer his son Reuben's incest with his concubine Bilhah (Gen. 35:22). What a shameful thing this was for Jacob! Because of Reuben's defilement, he lost the birthright, which was then given to the sons of Joseph (49:3-4; 1 Chron. 5:1-2).
Genesis 37 speaks of Jacob's suffering the loss of his beloved son Joseph. Jacob's sons conspired to do away with Joseph, and then they lied to Jacob about what had happened. For many years Joseph was separated from Jacob, who thought that he had died.
Because of the famine in the land, Jacob was forced to send his sons to Egypt to buy grain. As a result, he had to suffer the danger of losing his son Simeon and his youngest son Benjamin (42:18—43:15; 44:9-34). When Jacob's sons returned from Egypt with the grain, Jacob learned that Simeon had been detained there (42:24), and he also learned the sad news that Benjamin had to go to Egypt. After he heard this, he said, "Me have ye bereaved of my children: Joseph is not, and Simeon is not, and ye will take Benjamin away: all these things are against me" (v. 36). Although Reuben promised to bring Benjamin back, Jacob did not listen to him. Rather he said, "My son shall not go down with you; for his brother is dead, and he is left alone: if mischief befall him by the way in the which ye go, then shall ye bring down my gray hairs with sorrow to the grave" (v. 38). Eventually, due to the severity of the famine, Jacob was forced to send his youngest son with his brothers to Egypt to buy grain (42:4, 36; 43:1-15). What a suffering this was to Jacob!