For years I have wondered what the connection was between chapter 27 of Tehillim (L’Dovid Hashem Ohree) and the month of Elul. I could not understand what the underlying message was. I have read numerous explanations, however it was only yesterday when I finally discovered an explanation that satisfied me.
During the month of Elul we take upon ourselves new mitzvos and concrete ways that we will be better in order to properly prepare for Rosh Hashana. Immediately after we take this step forward, obstacles arise and people may notice that we are “changing” and try to impede our personal growth.
Beginning Rosh Chodesh Elul we say chapter 27 of Tehillim after davening. In the last pasuk (27:14) we are given our daily dose of encouragement; Hashem reminds us that He recognizes our latest struggle and tells us not to lose our resolve:
“Hope for Hashem, be strong and He will give your heart courage, and hope for Hashem.”