Ya’akov in his dream sees the image of a ladder, “V’hinei malachei Elokim olim v’yordim bo,” with angels were going up and down “it”. The pronoun “bo” sounds like it refers to the ladder; however, there is another view in the Midrash (68:18) that explains that “it” refers to Ya’akov himself (unlike in English, there is no difference in the Hebrew between “it” and “him”). The Midrash continues that angels flew to the Heavens and saw the image of Ya’akov engraved (so to speak) on G-d’s throne, but then they descended to Earth and found him slumbering and laughed and mocked him.
The parsha continues, “V’hinei Hashem nitzav alav,” telling us that Hashem stood above “it/him”. Once again, we have a similar debate in the Midrash (69:2) as to whether the ambiguous pronoun refers to the ladder or to Ya’akov himself.
What is the nekudas hamachlokes here?
The two views of the Midrash offer us two perspectives on Ya'akov's dream. The first view of sees Ya’akov’s dream as a look outward at the angels coming and going in the world, governing how things are run. Above this entire mechanistic framework, above the ladder, stands G-d himself, controlling everything. Ya’akov is reminded, as he stood on the threshold of entering Lavan’s home court, that events are not happenstance, but are controlled by an army of messengers sent from above.
The second view sees Ya’akov’s dream as a look inward, at the coming and goings of his own thoughts. R’ Chaim Volozhiner (Nefesh haChaim 1:19) writes (based on a Zohar) that the ladder of Ya’akov dream refers to his own soul. Rav Bloch in the Shiurei Da’as explains that the angels of Ya’akov’s dream represent his kochos henefesh, the characteristics and traits of his personality, his self, his soul. Ya’akov’s saw the heights to which his potential could carry him, but also saw the slumber and weakness into which he could fall, a vision of lost potential worthy of being mocked. It’s not the transcendent image of G-d who controls the outside world and nature which appeared to Ya’akov, but rather the image of G-d as standing above him, relating to him personally, aware of and measuring his thoughts and deeds (see Sefas Emes 5651).
(As an aside: a great post on how to approach Midrash.)