We all know that we can’t just wake up on the day of Rosh Hashanah and hope everything will be the best, and that we must spend significant time beforehand preparing, and this is exactly why we have Elul and the days of selichos. The question is, why do we need this?
I saw an amazing mashal from Rabbi Avi Wiesenfeld which answers this question, and highlights very beautifully what Elul is all about:
There was once a very wealthy man who owned a magnificent home with a large wine cellar. In this cellar he stored his treasure: an entire collection of the most exquisite and rare wines, gathered from around the world over decades. It was one of the most valuable wine collections imaginable, and he was immensely proud of it.
Whenever honored guests would visit, he would seat them at his table and, as was his custom, send his butler to fetch a bottle from the cellar. The butler, who knew the collection well, would always select just the right vintage—something befitting the guest’s honor and stature.
