Pastor Kathy and Pastor Steve Gray my teachers, World Revival Church, Kansas City, spoke about this very idea. Blessings both pursue us and over take us. “Moses then added his own blessings and warnings to those given by G‑d at Mount Sinai.
[Moses promised the Jewish people, “If you remain faithful to G‑d’s covenant,] all the following blessings will pursue you and overtake you.” Deuteronomy 28:2
We are taught that on the Jewish New Year (Rosh HaShanah), G‑d decrees our livelihood and health for the coming year. And yet, we pray every day for health, sustenance, and many other Divine blessings. Is this daily prayer necessary, in that all has already been decreed on Rosh HaShanah?
This verse provides the answer to this question: G‑d’s blessings both “pursue” us and “overtake” us. On Rosh HaShanah, all the blessings necessary for their respective purposes descend (“pursue” us) to a certain level of reality where they wait in storage to be drawn down further (“overtake” us) into our physical world. The vehicle for bringing blessings down to us is our daily prayer and devotion to G‑d.1
Or HaTorah, Devarim, vol. 2, p. 1089.