In that Judaism's High Holy Days are taking place, at this writing, it is perhaps a bit late to recommend this book; a significant part of it
concerns the month leading up to Rosh Hashanah and Yom Kippur. Yet I've read Preparing Your Heart for the High Holy Days, by
Kerry M. Olitzky and Rachel T. Sabath, a couple of times, and enjoyed it very much.
https://www.amazon.com/Preparing-Your-Heart-High-Holy/dp/0827605781/