Tzipiyah.com

It is known that the month of Cheshvan is known as “Mar” Cheshvan, bitter Cheshvan, because of its lack of holidays. Why is it that this month is so empty of holidays?
Rav Kook, in Meged Yerachim, writes for the Month of Cheshvan: “When the soul is illuminating, even a cloudy sky can give bright light” (rough translation).
The message is clear. After the intense month of Tishrei where almost every day has special significance and where we continuously grow, now we are put to test. What are we going to do in a regular, day to day, life? How will we react in a month devoid of holidays?

We can look at that month as a cloudy and dark month. Or, we can recognize the fact that its cloudy but also that it hides some deep light behind the clouds. And when our soul is illuminated after such an intense month of growth, we can attain this light even through the clouds.

The light of the Month of Cheshvan is very deep. Most of the time, the deeper the thing, that harder it is to get to it, the less obvious it is. May all our preparations of the month of Tishrei give us enough strength to find the light inside the month of Cheshvan. Chodesh Tov!