We’ve already spoken about how Elul is a time for introspection (see here). The King (a.k.a. Hashem) is in the field and ready to listen! We have a special ability to connect more deeply to Hashem from now through the Chagim. Whether it’s in prayer, learning, chesed, or something else there are so many ways and places to channel it.
This is a time of year where things can come up emotionally and spiritually. Maybe you’re struggling with your relationship with Hashem or with another person and are looking for more ways to cope and grow. Maybe you just want more information about what is actually going on at this time of year and how to focus on the meaning of Rosh Hashanah. Maybe you want to connect more deeply in prayer. Maybe you’re deeply confused or stressed about teshuvah and in need of some answers that ease your soul a little bit.
Whatever you’re dealing with, there is a book for you. Here, we’ve got a list of 10 amazing ones that will undoubtedly boost your High Holiday season. Pick the one that interests you the most and dive in! Then let us know what you thought.
60 Days: A Spiritual Guide to the High Holidays
This one is a workbook as much as it’s a guide. In this interactive work, Simon Jacobson leads you through each day of Elul and Tishrei with information about the day as well as an intention to keep in mind. Each day has an exercise for your personal development to do too, so you can tangibly feel closer to your goals and more connected to your essence by the time the High Holidays are over.
Link: (60 Days: A Spiritual Guide to the High Holidays, $29; amazon.com)
Teshuvah
Teshuvah can be a daunting idea if you don’t know much about it. As Rabbi Bernstein writes, “The sensitive soul approaches these days with a blend of anticipation and reverence, of hope and awe.” In this book, he hopes to educate the reader and through that knowledge, help them connect more deeply to the meaning and spirit of these important, holy days.
Link: (Teshuvah, $25; amazon.com)
Soul Powered Prayers
Whether you’re a newbie to the world of Torah or a seasoned vet, you still may not fully connect to the Shmoneh Esreh, or Amidah, the standing prayer. It’s one we will say often during the High Holidays. Even if we’ve already recited it dozens of times, it can be hard to inject real meaning into the words. Rabbi David Aaron had a moment while he was in yeshiva when he was davening (praying) and stopped himself, realizing he had questions flooding in about what he was actually saying. As a result, he got to work researching, analyzing and thinking further about the text of this prayer. This book is the culmination of all that and sure to enhance your own spiritual experience.
Link: (Soul Powered Prayers, $10; rabbidavidaaron.com)
Conversations with God: Prayers for Jewish Women
Ruchi Koval made an appearance here on Chai on Life last week. In her article, she shared both inspirational and practical words of wisdom about how to enhance your own prayer experience. This book does that even further. She takes common prayers that we say and breaks them down into her own words, in the hopes of helping the reader connect more deeply. In the modern world we live in, it can be hard to relate to words written so long ago. Ruchi’s goal is to help women everywhere find that deeper relationship with Hashem through the text. It’s a book that you can use as a reference to enhance your prayers this High Holiday season and beyond.
Link: (Conversations with God: Prayers for Jewish Women, $20; amazon.com)
40 Days: Inspiring Daily Lessons in Teshuvah, Tefilah and Tzedakah
This book tackles the topics of teshuvah, tefilah and tzedakah — the three pillars of the High Holiday season. The author asks and answers insightful questions like, “Why doesn’t our teshuvah last forever?” and “How can we learn to concentrate more intensely while praying?” It’s a book you can take slowly yet get something out of almost immediately — the perfect companion.
Link: (Forty days, $13; kesherstam.com)
The Power of Teshuvah
The real power of this book is that Rabbi Heshy Kleinman breaks down teshuvah into five minutes a day. It’s an easy one to integrate into your morning or nighttime routine and learn easy yet effective ways to start practicing real teshuvah. He shares strategies, laws and personal development tips to really take the practice of the teshuvah to the next level and make tangible steps in your life.
Link: (The Power of Teshuvah, $12; amazon.com)
Battle Plans: How to Fight the Yetzer Hara
While this book doesn’t have teshuvah in the title, its focus on battling the yetzer hara (evil inclination) couldn’t be more appropriate for this time of year. The yetzer hara is the culprit of so many of our struggles in life and it takes constant battling to keep it in line. Written by wise women Sara Yoheved Rigler and Rebbetzin Tziporah Heller, this compact guide teaches you strategies to take at your own pace. Grab a friend and learn it together — you can discuss and challenge each other as you set out to have your best year yet.
Link: (Battle Plans: How to Defeat the Yetzer Hara, $26; amazon.com)
The 40 Day Challenge: Daily Jewish Insights to Prepare for the High Holidays
Rabbi Wildes knows how to make deep Torah concepts approachable and accessible. In his new book, The 40 Day Challenge, he has wisdom for each day of Elul and the days of Rosh Hashanah and Yom Kippur to both inspire and provoke you to become even more connected. Each daily reading has a challenge question at the end which you can think on or use as a “spiritual diary” to log your thoughts, work and intention at this time. It’s a must-have for the bookshelf.
Link: (The 40 Day Challenge, $17; amazon.com)
Emunah with Love and Chicken Soup
While this one isn’t specifically a High Holiday book, it easily can be. The biography on Rebbetzin Henny Machlis will undoubtedly inspire you to grow in emunah and so many other aspects of Jewish life. Whether you’re hoping to increase your chesed (loving kindness), feel more connected in prayer or even become happier, there is a lesson or two in this book for you. The author, Sara Yoheved Rigler, herself uses it in that way. It’s one you won’t regret picking up and will constantly want to refer back to.
Link: (Emunah with Love and Chicken Soup, $30; amazon.com)
Chofetz Chaim: A Daily Companion
The main reason we don’t have the third Temple built today is because of sinat chinam, or baseless hatred. Something we constantly need to be focusing on is how we can become better people to our fellow Jews and show more love. One mainstay in doing that is to work on removing lashon hara (gossip) from our speech. When you dive into the topic, you may find that so much more constitutes as lashon hara than you may have thought. By getting this pocket guide by the Chofetz Chaim on proper speech, you can start to take active steps to banish hurtful words from your repertoire and make a huge difference in the hopes of bringing Moshiach.
Link: (Chofetz Chaim: A Daily Companion, $17; amazon.com)
What’s on your High Holiday reading list? Let us know in the comments!
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