The description of Yosef's journey to meet his brothers is exhaustive in its detail; yet for all its verbosity the text seems to conceal as much is it reveals:
"He (Yaakov) said to him (Yosef), 'Go and see the welfare of your brothers and the welfare of the flock and bring word back to me; And he sent him from the valley of Chevron and he came to Shechem. And a man found him and behold he was wandering in the field; and the man asked him, saying 'What is it you seek?' And he said, 'I seek my brothers, tell me please where are they grazing?' And the man said, 'They went from here, and I heard them say let us go to Dotan.'"
The Torah mentions here that Yosef was wandering "basadeh"- "in the field;" it's a chilling revelation. "The field" is the scene of one of the most infamous crime in the history of humanity. Indeed, while this crime is the first time the Torah mentions something happening "in the field," it is also the first time we see an encounter between two hostile brothers: "Kayin said to Hevel his brother, and it was when they were in the field (basadeh)." (Bereishit 4). The result of this meeting is well known: "Kayin rose up to Hevel his brother and killed him." (ibid)
Fields are open places, they offer no protection; they have no landmarks which makes it easy to lose one's sense of direction or get turned around. Yosef himself is "wandering," confused, and his bewilderment is compounded by the stress and drama of the situation. One might think that Yosef's wandering is a direct product of his physical surroundings, but it could also be the result of a deeper, more significant confusion. Several commentaries try to explain the reason behind his wanderings.
Malbim explains Yosef's confusion based on the plain meaning of the text. Yosef went to search for his brothers in Shechem and could not find them there, so now he has no idea where to look or how to continue. (37, 15) Yosef knows that the brothers could not have gone far with the sheep. He was confused because shepherds usually travel slowly with their flocks, allowing them to graze along the way from one pasture to another; they don't normally decide to leave one place and go to another specific, predetermined destination. The man's revelation foreshadows what is to come. At this point Yosef's search is no longer confusing, he needs only to decide if he should follow them, and the reader is left to follow along with his decision.
While the Malbim took this episode at face value, others saw it as shrouded in mystery. Such opinions have claimed that the man was an angel (an opinion that appears as early as the midrash) or that the man sought Yosef out, and not the other way around, because he was sent by God to direct Yosef. This assertion is backed by hints in the text which indicate the man knew Yosef's identity , as well as that of his brothers, plus their intended destination. Additionally Yosef's reply, "I seek my brothers," is a loaded statement that foreshadows a drawn out search, an attempt to discover who his brothers are on a deeper, spiritual level that will ultimately bring peace between the brothers. Obviously the path to this destination is far more complex than the journey that takes Yosef from his physical location in Shechem to that of his brothers in Dotan. (Zohar Vayeshev; Alshich, and more)
Rav Tzvi Hersch Spira of Munkatsh raises a third option. He explains Yosef's wandering as an internal religious dialogue; Yosef was trying to understand what his halachic responsibility in this case. Yosef went to Shechem as his father asked, so in a way he fulfilled his father's instruction; perhaps he is now free from obligation. On the other hand it's possible that his brothers are in the outskirts of Shechem, which means he has not yet completed his mission:
When he didn't find them in the field he was also wandering, meaning he was confused in his search when he was in the field, he said the end of the statement instructed [me] to walk so that I found them, yet today they are not in the borders [of the city] or in the fields, so then he was 'wandering' and confused in his attempts to understand the words of his father. (Igra Dkala, Vayeshev)
Rav Tzvi Hersch understands Yosef's confusion as the hesitation and careful consideration of a Torah scholar studying Talmud statements, examining every aspect. The Malbim views him as a person confused by complicated circumstances that don't add up; even though he has doubts he still needs to make a decision. While the Zohar sees Yosef on a journey guided by the heavens, on a path that has been carefully laid out. Each of these commentaries describes his confused wanderings based on what they are familiar with and what corresponds to the character of their commentary. Each one describes a different aspect of the challenges Yosef faced. He has a dilemma he must solve. He is aware that his dreams lead the way and that he is uniquely guided by Divine Providence. And he uses logic and his whits to come to rational conclusions concerning his journey.
Yet there is no commentary that combines all these questions into one experience. In its place we can only imagine that Yosef is well aware of everything that is holding him back and preventing him from escaping his bewilderment and continuing on his way with surety. And overall there is one question that is more bewildering than all else- how is he supposed to navigate his way through all these different thoughts, considerations, and feelings. He is wandering among all the options and methods he has at his disposal, together they make a maze he must navigate so he can decide what to do next.
Should he act according to his intellect and react to the situation just as any other logical person would do in his place?
Should he allow fate to lead him on the path he would end up following anyway?
Or should he initiate action on his own, dissect what he knows, and treat every obstacle in his path like a text that he must decipher, hints sent from heaven so that he can realize his mission in this world?
It's possible that all three approaches lead Yosef on the path he must take to continue on his mission in search of his brothers, brothers who have wandered far from any feelings of fraternity. His gut instinct along with his halachic obligation to honor his father both point him down the road that leads to one shared destiny. A destiny where he and his brothers will eventually have to choose to focus on the bonds they share above the distances that separate them.