ויגש וישק לו וירח את ריח בגדיו ויברכהו ויאמר ראה ריח בני כריח שדה אשר ברכו ה' ... (כז-כז)
Rashi comments on the seemingly peculiar order of how the malachim went on the ladder in Yaakov’s dream; first they were עולים - going up, then יורדים - going down, instead of יורדים first. He explains that first the malachim of Eretz Yisroel took leave of Yaakov Avinu, and only afterwards, the malachim of חוץ לארץ descended to further protect him.
One of the earlier Rebbes, while learning Chumash as a child, had an uncanny knack for asking Rashi’s queries on his own even before seeing the words inside. It is told that as they learned this above posuk, his cheder Rebbi expected the prodigious child to ask Rashi’s question here. He did not. When asked why not, the child wittily responded “It was only a dream!”
Indeed, it was a dream, but both he and we know that Yaakov’s dream was anything but ordinary. Which brings to mind the well-known legend of the Ponovezher Rav zt”l embarking on the construction of his famous yeshivah during the height of World War II. People were astounded and expressed their disbelief. “Are you dreaming?!” they asked with wonder and consternation. “I may be dreaming,” the Ponovezher Rav replied, “but I’m not sleeping!”
Perhaps there’s another possible explanation to the above posuk. The Medrash says "עולים ויורדים בו" - in him, referring to Yaakov himself, not the ladder. The spiritual well-being of one’s angel is directly correlated to the person himself. If the person is enjoying a spiritual aliyah, then עולים - his malachim too, will rise. If he declines chas v’shalom in ruchniyus, so will they. Thus, the Torah, urging us all to improve, first writes "עולים". And since understandably there are inevitable bumps in the road, it also says "יורדים". The machshava is that we must realize that like the ladder itself, there are ups and downs in life. As long as our life’s game of “Chutes & Ladders” progresses mostly upward, we cannot be discouraged by the occasional inevitable slide. Pick yourself up, brush yourself off, and charge upward. If you do so, you’ll be a winner.