First, my confession. And it comes with a slice of guilt. I never liked the High Holidays. In fact, as the thoughts of family and friend-filled Passover seders would start to fade each year, I would begin to think about the impending Days of Awe with a knot in my stomach and a distaste in my mouth that even the thought of sweet apples and honey could do little to relieve. What’s worse is that as a Jewish educator, I am charged each September to teach about the meaningfulness of these Tishrei days: The opportunity to reflect, to return, to become a better person.
What was really swirling through my mind was the idea of sitting through seemingly endless services, uninspiring sermons and a day of fasting and praying that had a sadomasochistic feel to it.
I would ask myself why the need for the hours on hours of prayers, many of which were repeated over and over. And wasn’t it enough to hear the words of Kol Nidre once? But three times? Really? All while standing and listening to musical notes dragged out for what seemed like days. And I was cynical of the whole spectacle, of synagogues having to move locations to accommodate larger-than-normal crowds (reminiscent of college days when on final exam day the lecture hall would fill up with students who had not shown up all semester for class). And of the fashion shows and maneuvering for the best seats that money can buy.
But all of these thoughts changed about a decade ago, when I was in my late 30s. The holidays were approaching, and I was anything but looking forward to them. Then a colleague introduced me to a work booklet called Where Are You? by Jael Greenleaf, subtitled The Inventory of the Soul in Preparation for the High Holy Days. Each page included a verse from the High Holiday prayer Ashamnu. Following the verse was a trigger for thinking and a half page for written reflection. Every night I would read the page and journal.
That year, as I reflected upon the High Holidays just past, I realized not only were they meaningful, but I actually felt refreshed and empowered. I reflected on it after the holidays and realized something that had never occurred to me previously: Every year until that year, I would walk into services on the holidays and expect to be somehow transformed. I would enter the sanctuary on the first night of Rosh Hashanah and unconsciously be thinking: Rabbi, Cantor, do your work. Make me a better person. Make me feel something.
Only that year, on the cusp of my fifth decade, did I realize that this was my responsibility. I couldn’t expect to walk into the final exam having not done the work and then expect to ace the test.
Every year since I have done my homework. Beginning the first day of Elul (traditionally the beginning of the days of preparation for the holidays) I have made a plan to get me into the mindset of the challenging work of reflection and self-transformation. One year I bought a book that included a reading for each day of the month preceding the High Holidays. One year I journalled each night, focusing on ways I hoped to do better in the year ahead. Another year I read a psalm traditional for this time of year each night.
A few years ago I decided to focus my preparations on a specific goal and aspect of my life that was troubling me. At the time I was feeling disconnected from friends and social relationships. It was taking a toll on my spirits, and I knew I needed to do something to repair this. I decided each day to call a friend with whom I had not spoken for a while. By the end of the month, having spoken with or left voicemails for 30 friends with whom I had been out of touch, I found myself feeling much less disconnected and significantly more whole. Walking into services on the first day of Tishrei I was ready to engage. I had done my homework.
This year I am feeling less charitable than I wish I were. I have decided that every day I will put a dollar in my tzedakah box. My hope is that I will make a concerted effort to carry this over for the rest of the year and beyond. And when I sit in services this year I know I will reflect on my active engagement in the Elul preparations.
This year, as I have these past several years   when I teach about Elul and prepare for self-transformation and when I journal with my students about this, it will be from my heart.
And when I walk into services on the first evening of Rosh Hashanah, I will be able to say, as Abraham and Moses say in the Torah and as the cantor chants on Kol Nidre evening, “Hineni, here I am. I am here. I am ready.”