The most obvious association with ladders would be the one Yaakov saw in Parshat Vayetzeh.
But why would angels need ladders? Usually, angels simply appear. In other places, they fly. So why should Yaakov see such a strange vision?
When we climb a ladder, skipping a step is a near impossibility. That, of course, is a great analogy for our spiritual lives. As with a ladder, trying to skip steps is fraught with danger. Even if we don’t fall, we are likely to lose our balance. Given all the seemingly unnecessary obstacles Yaakov would face in Lavan’s house, it was important for him to appreciate that there is no flying, only climbing – one slow and painstaking step at a time. He also saw angels descending, so as to understand that all paths have two directions. What goes up can also come down.
Finally, why angels? Perhaps to show that spiritual ladders are not completely like physical ones. If there is a spiritual equivalent of gravity that makes it easier to descend, it is offset by G-d’s assistance when we decide to ascend – we just have to choose that direction.
