The Deeper Meaning is a book filled with questions relating to the world and Judaism that so many of us have thought about at one time or another. Instead of pushing those questions out of our minds, author Uri Kestenbaum ensures that we address these topics, ranging from free choice to Shabbos to self-esteem, while discovering the hidden meaning within them.


After seeing this fascinating and thought-provoking book, we had a few questions of our own for the author!


Why did you write this book?

The truth is, I never sat down to write it. There were many times when I would think and talk-over all sorts of discussions about life with friends, and I would then write down my thoughts on the things we spoke about. Eventually I came to realize that a lot of the things I was discussing and writing were about things that many other people think about as well.

Reading through The Deeper Meaning, it might seem like it’s a transcription of someone talking; and that’s exactly it. I hope to touch upon topics that people think about and discuss out loud or internally.

Who is the ideal reader of this book?

Anyone who enjoys really getting to the bottom of what is the darher, the essence of common Jewish themes, will enjoy this book. It’s a thinking book, and, understandably, honest thinking is not always the easiest thing to do. Readers can use each chapter as a resource to start discussions around a Shabbos table, or as a helpful guide for some soul-searching. Fans of Rav Dessler, R’ Akiva Tatz and The Shmuz should definitely make room on their bookshelf for The Deeper Meaning

Have the questions discussed in the book been asked to you by others or are they questions that come from you?

I think the questions in the book are really universal. Questions like, “What makes people get embarrassed?”, “Why do people cry?”, “What causes self-esteem problems in this generation?”, and so on, are questions that everyone thinks about at some time or another. So, yes, they are my own questions, but when I speak about them, I find that people pop their head up and say things like, “Hey! Ya, why are we so drawn after novels and movies?” I believe that there is much in the content that people will identify with and will feel as if someone is addressing their own inner thoughts.

What did you learn by writing this book?

The process of preparing something for the public requires clarifying things down so clearly that it can be readily understood. It was nice to think about how I could break things down into a palatable and entertaining mode. It got me used to simplifying. 

What challenges did you encounter when you wrote the book?

The truth is that there is so much to write about and not everything deserves its own chapter. I found it challenging to condense a lot of material into small enough chunks that would still be pleasant and fun to read. Sometimes I deleted whole pages in order to make it easy on the reader and let the ideas flow without being bogged down by too many proofs or counter-arguments.

What’s next for you?

You know, there’s so many amazing things that klal Yisroel is into these days. We have Yeshivos, Bais Yaakov’s, shiurim and unbelievable chessed organizations. I believe that we are ready, as a nation, to take what we have and upgrade it to the next level. I am, b’ezras Hashem, working on a project that can serve as a step-by-step guide to upgrading the level of our Jewish experiences one by one. I look forward to finding what works best for me, and hopefully sharing it with others who can benefit by jumping along for the ride!


Be sure to check out The Deeper Meaning here!