Rabbi Mark Wildes, founder and director of Manhattan Jewish Experience and author of The 40 Day Challenge, shares tips for spiritual preparation and lasting growth
With Rosh Hashanah just two weeks away, thoughts naturally turn to self-reflection, personal growth, and the desire to enter the Yamim Nora’im with a renewed sense of purpose. Yet achieving that sense of readiness does not always come easily.
We spoke with Rabbi Mark Wildes, founder and director of Manhattan Jewish Experience (MJE) and author of The 40 Day Challenge: Daily Jewish Insights to Prepare for the High Holidays, about practical ways to prepare emotionally and spiritually for the Yamim Nora’im, make the most of this unique period, and make changes we can realistically sustain.
We spend a great deal of time preparing practically for the Yamim Nora’im, but what does it mean to prepare spiritually and emotionally, and why is that preparation so important?
When Rosh Hashanah and Yom Kippur arrive, we often expect the experiences in shul to have a transformative effect on us. In my introduction to The 40 Day Challenge, I quote the famous line from Rabbi Soloveitchik, zt”l, who said, “Ein kedusha bli hachana — there can’t be any kedusha without real preparation.”
We know this from so many examples, including Shabbos. We can’t really appreciate Shabbos without preparing for it, and that goes well beyond preparing the three meals. The more you invest in something in advance, the more special it becomes.
Our ability to access the inherent power of the Yamim Nora’im may be limited without preparation. How much we experience during those days can depend largely on the Torah and avodah we take on beforehand.
Your book is structured around 40 days of preparation. What inspired that framework, and what is the significance of the number 40?
According to our mesorah, 40 days hold tremendous significance. Moshe Rabbeinu spent 40 days and 40 nights on Har Sinai, and when he came down and saw Bnei Yisrael sinning with the egel hazahav, he broke the luchot on yud zayin B’Tammuz. He then spent another 40 days beseeching God on behalf of Bnei Yisrael. It was then, on Rosh Chodesh Elul, that the Bnei Yisrael were given a second chance. Moshe was invited to ascend Har Sinai once again for another 40 days and nights, this time to receive the second set of luchot. He descended on Yom Kippur, when Bnei Yisrael received God’s complete forgiveness.
That’s why I structured the book as a 40-day journey. People don’t have a lot of time, but they want to feel they’ve done something to prepare for the Yamim Nora’im, and I believe we can have a greater impact through consistent daily practice. So I offer a little piece of Torah each day, with a different theme, drawing on the spiritual energy that HaKadosh Baruch Hu Himself established for Klal Yisrael, during this time on the calendar, to reunite with God.
And that’s essentially what we’re doing during Elul: we get a second chance to become reacquainted with God.
There’s also the famous idea of HaMelech baSadeh, “the King is in the field”. All year long, if someone wishes to see the King, they have to make an appointment, wait in line, and go through intermediaries to enter the palace. But during Elul, the King leaves the palace and becomes accessible even to the simple peasant. That’s the opportunity we all have during this period.
For someone who wants to prepare during Elul but isn’t sure where to start, what practical steps can help them get into the right mindset?
Study a little Torah every day. It doesn’t have to be The 40 Day Challenge; there are so many options. I think the Rambam’s Hilchot Teshuvah is amazing. According to tradition, its 10 chapters correspond to the Aseret Yemei Teshuvah, allowing you to study one chapter a day from Rosh Hashanah through Yom Kippur.
If you can’t devote that much time each day, you can still learn portions of Hilchot Teshuvah, or perhaps Hilchot De’ot, the laws of character traits, where the Rambam addresses bein adam l’chavero and many other aspects of self-improvement.
The goal is to study growth-oriented Torah, Torah that challenges you to move beyond where you are as you approach Rosh Hashanah and Yom Kippur.
What if someone doesn’t naturally connect through Torah learning? How can they find an approach to preparing for the Yamim Nora’im that genuinely resonates with them?
If learning doesn’t resonate with you, I would suggest focusing on an act of chesed. Think of someone in your neighborhood who may be in need. A friend of mine recently shared that he regularly visits a man with ALS. Chesed is not just about giving money – that’s tzedakah. Chesed means giving your time and being there for someone else.
Wherever you are, look for opportunities to engage in hands-on chesed. For example, there’s an amazing kosher soup kitchen and food pantry in Brooklyn called Masbia, where you can serve food or work in the kitchen, cutting onions or peeling potatoes.
Chesed is also something you can do with your kids. When our kids were little, my wife and I would take them to Masbia or find another way to give back together. It enriched our lives on so many levels, including the way we interacted as a family.
Many people find the lengthy tefillot of the Yamim Nora’im difficult to connect to. What can we do beforehand to make the experience in shul more personal and meaningful?
First, if possible, attend a shul that you find engaging. Find a place where the rav’s drasha and baalei tefillah inspire you.
Second, find the right machzor. Look for one with commentary that helps you understand the tefillot. There are also wonderful sefarim you can learn beforehand, or even bring to shul, to help you connect more deeply. It’s very hard to be moved by ideas we don’t really understand.
Lastly, focus on quality over quantity. It is important to approach the tefillot with kavanah, focus, and reflection, rather than concentrating only on getting through every word. One of my teachers, Rabbi Dr. Norman Lamm, zt”l, used to say, “We may get through the prayers, but are the prayers getting through us?”
That’s really the goal of tefillah. Tefillah is avodah shebalev, service of the heart. If our hearts aren’t in it because we’re playing catch-up or checking off boxes — I said this tefillah, I said that tefillah — but we don’t feel transformed or spiritually connected, then something is missing. The focus should be on the quality of our tefillah, not simply the quantity.
The Yamim Nora’im often inspire us to make changes that are difficult to sustain. How can we approach personal growth during this period in a way that is realistic and lasting?
First of all, read James Clear’s Atomic Habits. I’m actually teaching a class called “Holy Habits” based on a lot of the material in the book.
One of its key lessons is to choose small changes that you can sustain over time. Clear gives a great metaphor: If a pilot, about to fly from LA to New York, adjusts the plane’s course by just a tiny amount, at first the difference is almost imperceptible. But if he sustains that change over the course of the entire flight, he’ll end up in Washington instead of New York!
I think a lot of us have very big eyes when we come before HaKadosh Baruch Hu on the Yamim Nora’im. We want to make bold promises and pledges, but they’re often not realistic. It’s like the gym in January: You have to wait 10 minutes for a treadmill. By February, there’s no line, and by March, the gym is half empty. What happened? People set goals that were too ambitious to sustain.
The same principle applies to personal growth. Whatever mitzvah you want to take on, whatever positive change you hope to make, or negative behavior you want to leave behind, don’t set the bar so high that your goal becomes difficult to maintain. Choose something modest and commit to it over time.
For example, you might think, “I didn’t do enough learning this year. I’m going to start Daf Yomi.” If you can devote an hour to it every day, great. But if that isn’t realistic, choose something more manageable: “I’m going to learn for 15 minutes a day,” or set another modest goal you know you can maintain.
The Gemara says, “tafasta meruba lo tafasta — If you grab onto too much, you may end up with nothing.” That’s a very important message. Small changes, sustained over time, take us much further than dramatic changes that don’t last.
Rabbi Mark Wildes is the founder of Manhattan Jewish Experience (MJE), a highly successful outreach and educational program that has reconnected and engaged thousands of unaffiliated 20’s/30’s in Jewish life and provided a venue in which 402 couples have met and married. He received his smicha from Yeshiva University, and holds a JD from the Cardozo School of Law and a Master’s in International Affairs from Columbia University. Rabbi Wildes is the author of Beyond the Instant: Jewish Wisdom for Lasting Happiness in a Fast-Paced Social Media World, The 40 Day Challenge: Daily Jewish Insights to Prepare for the High Holidays, and The Jewish Experience: Discovering the Soul of Jewish Thought and Practice.