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Although I haven’t written in a diary for over thirty years, the urge to transpose feelings into words has never left me. A few days before Rosh Chodesh Elul, I received an email from the OU Women’s Initiative introducing a forty-day journaling project whose goal was to “delve into our past year’s experiences, and explore our future goals and aspirations.” I signed up immediately, lured in by the promise of accountability, structure, and a daily writing assignment.

After receiving my journal, I had the option of working on it online or printing it out. Although my handwriting is deplorable, I chose the printed version because I wanted to experiment with a modality called ‘stream of consciousness,’ a method of writing where you write exactly what you think, as you’re thinking it, without internal censorship. Intuitively I knew that if I worked on it online I would be tempted by the delete and backspace buttons. I wanted to eradicate my inner editor and see what would happen.


Day one: Identify one habit or behavior that held you back in the past year. How can you work on changing it? Easy, I’m a procrastinator. But unwilling and unready to confront my flaws, I leaned into my self-professed bad habit and started to look at the prompts for the upcoming days.

Day two was infinitely easier than day one: Describe a specific challenge or obstacle you faced and how you overcame it. Ha, there weren’t enough lines on the page for this one. I wondered if I should start day two before day one, just to get my brain in the right headspace. No, no cheating. I decided instead to take a little time and ruminate about my habits before I started writing. Part of the daily exercise was not just to respond to the prompt but also to create an action plan, presumably with the intent of attempting to eradicate, or at the very least mitigate, the faulty thought process or behavior that had been revealed on that day. It was the action plan that tripped me up – that revealed the lie, the lie I told myself, the lie that covered an uncomfortable truth whose raw and utter veracity made my heart stutter and my stomach twist. Identify one habit… (I picked up my pen and spewed my guts onto the paper.) … that held you back in the past year. I’m not sure if the behavior held me back, but it certainly made me feel ugly, petty and small, a flaw so much worse than procrastination, one whose revelation made me wonder if I even needed to finish out the rest of the journaling experience, since the remediation of this trait would require a considerable amount of introspection and most certainly could not be encapsulated in a three-line action plan.

When we think about teshuva, we usually think about repentance for specific, concrete transgressions. I lied. I stole. I was stingy. But repentance for personality traits? How do you repent for being yourself? The answer to this is simple but seemingly insurmountable: You need to transform yourself into a different person. The Rambam in Hilchos Teshuva (7:1) acknowledges that the teshuva journey for specific sins differs from the teshuva journey for undesirable aspects of one’s personality. Rav Aharon Lichtenstein commented that the Rambam’s language of “yishtadel adam laasos teshuva” (man should try to repent) is very curious. In reference to actionable sins, the Rambam is unequivocal about the necessity of a complete and total teshuva, but about teshuva for personality flaws, he acknowledges that this endeavor is no easy task, hence the use of the word “try.” We usually use the term baal teshuva to describe someone who abandons a secular life and becomes shomer torah u’mitzvos, but the truth is that since according to the Rambam refining our personalities is a lifelong journey, we are all considered to be baalei teshuva.

At the beginning of week two, my enthusiasm for the project waned and I wasn’t sure why. Maybe the scope of it was too large, its daily introspective demands too overwhelming. Maybe confronting myself daily was a skill that required me to wade shallow before I dove deep. I decided not to write in my journal that day, which made me hyper-aware all day long that I was not writing in my journal that day.

Describe a time when you were able to let go of perfectionism and embrace imperfections. How can you continue to cultivate self-acceptance and self-compassion? This is a very difficult concept for me, especially during Elul. If I embrace my imperfections, if I accept myself as the flawed human that I am, what drives me to do teshuva? A basic tenet of our belief is that Hashem is perfect, and we are not. We are commanded to walk in His ways, but His footsteps are too wide, too deep; we are toddlers attempting to fly. Ironically, it was this existential impasse that plunged me back into reality, into the reality of a world where I was a walking cliche – an eager beaver who had bit off more than she could chew. I decided that if a journal prompt didn’t immediately punch me in the gut, I would concentrate on something else that day.

My grandfather’s nineteenth yahrzeit was on the fifteenth of Elul. Days before this, his namesake, my nephew Elazar, put on tefillin for the first time, and our family gathered for a seudas mitzvah. My brother spoke about our grandfather, about his simchas hachaim, his unwavering faith in Hashem, even after what he had endured during the Holocaust.

Describe a situation where you had to make a difficult decision. How did you navigate through it, and what did you learn from the process? Even after coming to America, my grandparents’ life was hard. After losing his job every Friday in order to keep Shabbos, my grandparents moved to Lakewood and became chicken farmers. My mother, a beloved only child, attended the yeshiva day school there until eighth grade. Although it’s hard to imagine a time when Lakewood did not have a Bais Yaakov high school, my grandparents had to make the difficult decision to send my mother away to live in New York for high school.

My mother was born in a Siberian labor camp, her birth and subsequent survival were nothing short of a miracle. There is no doubt that my grandparents wanted nothing more than to swaddle my mother tight and keep her with them forever. But G-d called to them, G-d tested them; take your child, your only child, your child who you love more than anything. On the second day of Rosh Hashana, we read about akeidas Yitzchak, G-d’s unfathomable command to Avraham to sacrifice his son. This is a troubling and confusing request, one that seems antithetical to every single thing we believe in. The Rav, Rabbi J.B. Soloveitchik, explains this: We are not commanded to literally sacrifice our children, but we are called upon to lead a sacrificial life. Hashem gives us many gifts – children, money, good health. We think these things belong to us, we made them, we earned them, we deserve them. But nothing is ours, and we deserve nothing. Everything we are given is a tool to serve Hashem. My grandparents knew that my mother was theirs, but also not theirs. They sacrificed their parental desires for the sake of their daughter’s religious future.

I’m pretty sure neither of my grandparents had the luxury nor the inclination to think about how difficult this decision was or what they learned from the experience. They were cut from a different cloth, one that was stronger and stitched tighter than the one we were sewn from. We read the story of the akeida on Rosh Hashana because on our own, we are unworthy. We ask Hashem to remember the sacrifices of our Avos, of our grandparents, and in their zechus, to show us mercy.

On this day, my grandfather’s yahrzeit, I had a flash of clarity. There are multiple stages of teshuva, corresponding to past, present and future. I regret what I did in the past, I confess my sins in the present, and I resolve to do better in the future. Many years from now, our grandchildren’s grandchildren will be davening on Rosh Hashana. They will harness that eternal power of zechus avos, a power that can save us from ourselves. The teshuva that we do today directly affects the outcome of the teshuva of our descendants. We are the avos. We are the generation who needs to lead by example, we are the generation who needs to live a life that is worthy of emulation, a life of sacrifice, a life of virtue. When our children cry out in the name of their forefathers, will Hashem look at our lives and say “Yes, your parents followed in my footsteps, I grant you another year of life because of their merit.” While on one hand this is a terrifying and troubling thought, it is also very beautiful.

I started the journaling project with the anticipation that it would bring focus and accountability to the month of Elul. I didn’t anticipate, however, that my definition of teshuva would change, that what started as an intimate, personal pursuit would expand into a more global experience. Rav Kook explains that this is the natural progression of teshuva, that in Elul we concentrate on our private journey back to Hashem, and on Rosh Hashana we broaden our outlook to that of the community and to the universe at large. This concept is further reiterated by the shape of the shofar itself, narrow at the beginning and wider at its end. Only when the narrow concerns of the “I” shift into the wider concerns of the “we,” only when we stand together as a klal, focused on the same goals; only then are we ready to sound the shofar and declare Hashem our king.

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Dr. Chani Miller is an optometrist and writer who lives in Highland Park, N.J., with her family. She is a frequent contributor to The Jewish Press.