I met one of my very best friends in the lobby of the Newark airport hotel 21 years ago.  We had both just graduated from college and it was day one of our adventure with Project Otzma, a program that sent new college graduates to Israel for a year of learning, teaching and adventure.  They would eventually divide us up by region, but that first day, we were all gathered together at the airport, nervously searching for someone who looked like they might be a possible friend.  Was it their clothing, or their confidence, their swagger, that made them seem like a potential ally on this scary journey?

For me, Sara was just the right combination of grungy and aloof to draw me right to her side.  She had long hair with one dreadlock at the back, and she was wearing an oversized hoody with lots of patches on it.  Just my kind of girl.  Cool, challenging, seemingly secure in who she was.  She had that “I’m clearly Jewish but I don’t care” attitude that was like a magnetic force to my nervous soul.  I knew a strong girl when I saw one and I attached myself to her like glue.

We spent that first night at the hotel bar together, drinking beer and sharing our most personal stories.  On the airplane, we made each other hemp necklaces—not kidding!–and exchanged simple silver rings, sure that those symbols of friendship would bind us to each other forever. We were not wrong about that.

When we landed in Tel Aviv, side by side, ready to take on anything if we had each other, we promptly learned that her region, New Jersey, would spend the entire year across the country from my region, San Francisco.  I was starting in the Negev, way in the south, and she would be as far away as possible from me, all the way in the north. When our kibbutz time was over, we were going to swap places, and so it would go, for the entire year.

Can you have a midlife crisis when you’re 22??

After a few brief moments of panic, we decided that this would not be an impediment to our budding friendship. We thought of a solution right away.  We wouldn’t see each other, so instead, we would write.

And thus began one of the most wonderful, creative, romantic, soul-nourishing times of my life, when Sara and I spent a year writing each other letters across Israel.  Israel is not a very big country, and we were passionate, lonely, searching girls, so we wrote to each other furiously, using the letters like a diary of our time abroad. I can still remember the moment when a letter would arrive, several times a week, in her distinctive handwriting.  I would resist the desire to tear it open, and wait until I could sit on my little single bed in my dusty kibbutz room, to get lost in her funny storytelling.  There is no doubt that the art of letter writing is disappearing with the whirlwind of technology that has taken over our world.  Getting a long-awaited email is great, but it just can’t replace the swell in your heart when a letter appears in your mailbox, hand-written, so familiar, with the promise of closeness by being able to touch the ink written by their hand.  I miss those letters immensely.

Imagine my surprise, then, when a few months ago, a hand-written letter appeared in my mailbox at CBT, neat and interesting hand-writing, not from Sara, but from someone I didn’t know.  The return address had a name and a number, and at the bottom was written:

Indigent Inmate Envelope Generated at Calipatria State Prison.

I hesitated before opening it.  Who??  State prison?  Where is Calipatria?? We looked it up in the office and discovered that Calipatria is in southern California, by San Diego.  I definitely don’t personally know anyone in a state prison near San Diego.  I opened the letter.

What I found was a friendly, eager letter from a Jewish man who is incarcerated and looking for spiritual connection outside of prison.  He had somehow read some of my writing online and was reaching out to make a connection, to learn more about Judaism.  “Please do not turn a blind eye to my letter,” he said, “I’m just seeking a pen-pal, someone of Jewish background with a good heart to write to from time to time…if you don’t mind being a supporter of knowledge of Judaism, please feel free to write back.”

“If you don’t mind being a supporter of knowledge of Judaism, please write back.”  How could I NOT write back??  Isn’t that what I was put here on this earth to do, to encourage people to seek out learning, to engage with their doubt and struggles, to help them connect with God?  I’ve never met this man with the clean, slanted handwriting, but I do know what it feels like when I’m supposed to step onto a path, and this was one of those moments.

So once again, I found myself with a pen-pal, albeit an unexpected one.  I began by sending him some more of my writing, on topics that I thought would resonate with him.  He always writes back right away, eager for more information and sharing bits and pieces of his life with me.  He asked for books, paperback only, so I sent him my favorite book at this time of year, This is Real and You are Completely Unprepared.  I tucked a note inside, wishing him deep refection around this season of teshuvah.  And then…he didn’t write back. For much longer than usual.

I realized as I waited for a return letter that I had begun to look for his letters when I walked in, from this unusual friend of mine.  But weeks went by and nothing.

Finally, a letter arrived, and he told me that the book came, thank you so much, but he wasn’t allowed to keep it, because it wasn’t sent directly from Amazon, so would I mind trying again?  The Torah says in Leviticus 19, “You shall not insult the deaf, or place a stumbling block before the blind. You shall fear your God.”  Here is a man trying to make the most of a terrible situation, trying to learn and grow.  If I can remove the stumbling block from his path, to help clear the way for his spiritual journey, then I will most certainly do that.  Back to Amazon I went.

In the last letter I received, my pen-pal told me that every year, he tries to put together tsedakah funds for Rosh Hashanah and Hanukkah, so that he and his Jewish brothers can feast and enjoy the Jewish holidays.  Last year they raised $300 for a beautiful meal and made care packages for each and every person. “Tsedakah is given,” he wrote, “because as human beings created in God’s image you have the responsibility to take care of your fellow human beings.  It is not an option, it is an obligation.” He is taking care of the people around him and has reached out to ask for someone to take care of him.

As I sat down to write my reflections for this service, I found myself trying to focus on other topics, but my mind kept wandering back to my incarcerated friend.  I don’t know what he did to end up in jail.  I don’t know how long he will be there.  I don’t know if I can trust him.  I don’t know if he will use the tsedakah money for good.  But I do know that it is not my place to sit in judgment of him as he tries to make the most of what seems to be a very hard life.  I do know that my work in this world does not only extend to the people in this room.  I do know that as much as we are each struggling for forgiveness, for peace, for release, so are he and his fellow inmates who are on their own spiritual journeys.

This is the first year that I have ever spent time imagining what it must be like to spend the high holidays in prison.  Every human being feels imprisoned by their own particular struggles, by the ways that it is uniquely painful to be alive, no matter your circumstances.  But how many of us take up pen and paper and reach out for help?

It’s hard to imagine that any of us need forgiveness for anything as significant as what would land a person in jail.  Some actions are definitely harder to forgive than others.  But that doesn’t minimize our pain or our need for teshuvah.  For me, this year at least, the experience of having my eyes opened by the reflective journey of a Jewish prisoner has made me more appreciative than ever of how our tradition offers every one of us eternal opportunities to redeem ourselves.  When I first started writing to him, I threw away many drafts of letters because I didn’t know if my messages would be useless to an incarcerated person.  Does he want to hear about honoring Shabbat?  Would it be insulting to him to hear my perspective on forgiveness, if I have no concept of the things that need to be forgiven by the people surrounding him?  What can I actually offer to a stranger whose life I cannot even begin to imagine?

And underneath all of those questions, the secret question that I didn’t want to admit to myself: what if he did something so awful that it isn’t forgivable?

As I have spent time with that last question, I have retuned over and over again to my belief that teshuvah, return must be possible for each and every person. If the desire for teshuvah is present, then it is ours for the taking, because we are at our core creatures of transformation.  I can’t do the work I do or walk through this world as a person of faith if I don’t believe that.  In the words of Rabbi Jessica Kate Meyer, “Even if you have broken your vow a thousand times, you carry within you the capacity to grow, to reprogram neural pathways. These holidays provide the scaffolding for that metamorphosis and the conviction that it is possible.”

That is not to say that it won’t be scary, or painful.  The real work of this season is terrifying, even if you know that forgiveness lies on the other side of the work, because the closer you get to authentic, honest transformation, the louder the voice within you screams to just stop it already and go back to pretending that we don’t need to face the ways that we have failed this year.  But we do.  It is the only way to the light.

We are about to hear in the Unetaneh Tokef not only the many ways in which we will fall this year, but also, that the handwriting of every person, chotam yad kol adam, will be inscribed in the book of life.  We each with our beautiful, unique, handwriting, will be called upon to do a cheshbon hanefesh, an accounting of our soul, and to pick up a spiritual pen and choose life.  It’s like a teacher asking you to write your own report card.  Only you know what hides in your heart and only you can write your name in your own hand.

As we move into this difficult section of liturgy, I invite us all to learn from the lost art of letter-writing that has been unexpectedly returned to me:

Forgiveness is possible.  Renewal is possible, no matter how dark it gets some days.  And above all, we are not alone on this journey of broken humanity.