Your doctor just called. The procedure is set for 40 days from today. Chances of success are not high. Plan for the worse. How will each day count and matter?

Your lawyer says the court date is set. 40 days from now. Prepare everything and be ready to defend your life. Chances are good but you got to work on it. Go.

Your fiancee found the perfect place for your wedding. Just 40 days away. So much to get done. Let folks know. Choose a diet.

Your rabbi writes a blog, tells you, “In 40 days we will be standing together in the presence of what’s most sacred to our lives.” How will we get ready – body, mind, and soul?

Yesterday, sitting in a busy restaurant in San Francisco’s Chinatown, mid travels, I cracked open a fortune cookie:

“Someone in your life needs a letter from you.”

All through dinner I was thinking about the High Holy Days ahead and how to prep for this annual journey of introspection. How do I make this life more present, happy, and helpful? The fortune cookie, of all things, gave me the key: write love letters, one each day for the 40 days leading up to Yom Kippur, to the who and what that matter most in my life.

“Dear Me,” I scribbled on a napkin, “It’s that time of year again and you and I are about to review life…this is the first of 40 letters, love and remorse and high hopes and best wishes. Ready? Let’s go. Love, me.”

So here we go. Again. The high and holy days are coming, and with them a brand new year and a brand new invitation for an annual check-in of what matters most. Not with fear but with love. What is blessed? What is in need of fixing? I’m excited for this journey.

I started this Prepent digital-blog-journey seven years ago because I wanted to begin the new year with as much intention and alignment as possible, and I knew that committing to it publicly would help me stay the course. Many have joined me over the years to reflect, perfect, and return to center.

“Repent” is just a loaded word for “take charge of your life.” It is, for me, a human-spiritual task more than a religious chore that implies faith or specific religious practice. Perhaps this process can be attempted and completed in just a day or two while fasting, but like all great art and acts of transformation, a longer and fuller process sustains a smoother ride and better impact. The “Pre” of Prepent is about extending this process of reflective change, so core to the Jewish life I lead. Our ancients came up with the notion that Elul, the month which wraps up the Jewish year, is our period for making peace and progress, coming clean and coming home. 40 days is just enough time to break a habit. Or make a new one.

I’ve come to really cherish this annual tradition. 40 days to look, honestly, in the mirror. 40 days to review the year that was, the relationships that need mending, the blessings that need counting. 40 days to plan for the next 365 days, the challenges ahead and the changes needed. 40 days for a better year, a better me, a better world. One love letter at a time.

Change is possible. It’s all about realistic and doable goals.

Just ask my life coach. I’ve been working with Laurie Gerber this past year and her spot-on, no-nonsense approach to the art of living has been immensely helpful. Laurie will be sitting on my shoulder as I write these daily letters, with some tips and links to help guide the process. She’ll even join me in NYC later in September for a LIVE Prepent event as part of Lab/Shul’s High Holy Boot Camp.

Laurie recently wrote a post “Designing Your (Spiritual) Life” on the differences between our spiritual yearning and our discomfort with typical organized religious life. But the article fuses both, focusing on the basic building blocks of human growth. “Designing your life,” she writes, “is an enormous act of self-love. And putting in daily spiritual practices can change everything about how you relate to yourself and your life, and they lay the foundation for profound wisdom unfolding in your life.”

So let’s do this together. One love letter at a time.

Starting on the first of Elul, Sunday, September 4th, I’ll post a short love letter, a personal reflection on change, that will hopefully inspire you to write your own and travel into this new year with more intention.

You can get the daily blog in your inbox by subscribing for free to our mailing list below by checking “Prepent” as a special interest, or you can follow Lab/Shul on FacebookTwitter, or visit my page over at The Forward.


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As seen on Lab/Shul :

Ready to re:love? Lab/Shul's video launch of the High Holy Days 5777!!!
Prepent Day 1: Let’s Fly