25 Sep REGRETS OR NO REGRETS?

“No regrets” is a
popular motto, a badge
of honor, and for some,
a way of life. It is even
a popular tattoo, a
slogan people literally
engrave on their skin.
Despite its appeal, it turns out living the “no
regrets” life isn’t really possible; we are
actually hard-wired to experience regrets and
that is a good thing. You see, regret doesn’t
just make us human, it can also make us
better. Brene Brown, the popular professor
and author, puts it well: “No regrets’ doesn’t
mean living with courage, it means living
without reflection.”
A few years ago, a group of researchers put
up a chalkboard on a New York City street
and asked random passersby to write down
their biggest regrets. The respondants were
from different walks of life, but their regrets
all had one alarming thing in common: the
word “Not.” They were primarily about
chances not taken, about words not spoken,
about dreams never pursued. By the end of
the day the chalkboard was completely filled
with tales of regret.
We aren’t in New York City and there is no
chalkboard here, but make no mistake, we
are here today on Yom Kippur to express our
regret, what we wish we could have done
differently, mistakes we made, things we
want to retract.
Rabbeinu Yonah writes in Shaarei Teshuva:
עיקרי התשובה: העיקר הראשון – החרטה. יבין
‘לבבו כי רע ומר עזבו את ה
The first primary component of the
repentence process is regret. One must
recognize in his heart the sinfulness and
bitterness of departing from Hashem.
What is charata and what role does it have
in teshuva? Are we meant to beat ourselves
up, knock ourselves down, be racked and
riddled with shame and guilt, or does charata
serve a different purpose?
Last year, Daniel Pink published a book
called “The Power of Regret” in which he
writes: “The conclusion from both the
science and the survey is clear: Regret is not
dangerous or abnormal. It is healthy and
universal, an integral part of being human.
Equally important, regret is valuable. It
clarifies. It instructs. Done right, it needn’t
drag us down; it can lift us up.”
Pink found that to make our regrets work for
us, we must respond systematically by
neither avoiding them nor perseverating over
them. He says there are three critical steps
that corelate with what the Torah has already
taught:
1. Reframe your regret. Does what you
regret deserve kindness or contempt? Does
the regret represent a moment in your life, or
does it define your life? We ask Hashem
yitamu chataim, eliminate mistakes, but not
chotim, those who make them. Even as we

spend today confronting what we have done
wrong, it is critical that we recognize they
need not define us.
2. Disclose your experience and regret –
Pink argues that using language, whether
written or spoken, forces us to organize and
integrate our thoughts. Instead of those
unpleasant emotions fluttering around
uncontrollably, language helps us analyze
them, limit them, learn and ultimately grow
from them. The Rambam sees vidui, verbal
confession, acknowledging mistakes and
shortcomings, as an indispensable, perhaps
the most critical, element of teshuva.
The Alter Rebbe connects the word charatah
with charitah, engraving. We have to admit
what we regret so that we can engrave what
we learned and ensure we don’t repeat it. We
cannot correct and repair ourselves without
articulating our regrets. Only when we
disclose it, confront it, and analyze it can we
learn from it and move on from it.
3. Extract a lesson. – Lastly, Pink says don’t
marinate, perseverate or get stuck. The
subtitle of the book is, “How looking
backward moves us forward.” The Rambam
says the step in teshuva after charata is
kabbalah al ha’asid, extracting a lesson for
the future, giving the regret meaning by
turning it into positive action. Like the Alter
Rebbe, the Alexander Rebbe links charata,
regret, to charita, engraving, as in the pasuk
in Yeshaya (8:1) b’cheret enosh, man
engraved. Charata is an invasive process
where we scrape away our most detestable
and despicable traits until they are gone.
For the Alexander Rebbe, charata, regret, is
not about the past, it is about knowing what
to purge and cleanse and repair in the present.
We can’t undo what we regret but we can
learn and grow from it by changing our
behavior now.
In his formula for return and repair, the
Rambam delineates the importance of regret,
only he uses a different term.
ּומַה הִיא הַתְּׁשּובָה.- הּוא שֶׁ י ַּעֲזֹב הַחֹוטֵא- חֶטְאֹו
ו ִיסִירֹו מִמַּחֲשַׁ בְּתֹו -ו ְי ִגְמֹר בְּלִּבֹו שֶׁ לֹּא -י ַעֲשֵׂהּו עֹוד
…ו ְכֵן- י ִתְנַחֵם עַל שֶׁ עָבַר- …ו ְי ָעִיד עָלָיו יֹודֵע-ַ
תַּעֲלּומֹות שֶׁ לֹּא י ָׁשּוב -לְזֶה הַחֵטְא לְעֹולָם …ו ְצָרִיְך
:לְהִתְו ַּדֹות בִּשְׂפָתָיו- ו ְלֹומַר עִנְי ָנֹות אֵּלּו -שֶׁ גָּמַר בְּלִּבֹו
The word “ִםֵחַנְת “is often translated as
“regret”, but it shares the same shoresh as the
word for “console”. When Hashem is
saddened by the behavior of humanity after
ו ַי ִּנָּחֶם ה‘ כִּי- says Torah the world the creating
is Hashem When .עָשָׂה אֶת הָאָדָם- בָּאָרֶץ
worried we will regret leaving Egypt, he took
כִּי׀ אָמַר אֱלֹקים פֶּן־י ִנָּחֵ֥ם ,route circuoutous a us
הָעָם בִּרְאֹתָ֥ם מִלְחָמָה ו ְשָׁ ֥בּו מִצְרָי ְמָה׃
Hashem is perfect, infinite, and omnipresent.
How is it possible for Him to have “regret?”
It must be םָחָנ doesn’t mean regret in the way
we clasically think of it, but it means to pivot,
to redirect. When performing nichum aveilim
we aren’t assisting the mourners in regret, we
are encouraging them to pivot and redirect

their lives, now without their loved one. In
the context of Teshuva, םֵחַנְתִמ isn’t merely
recalling the past and feeling bad and sad
about it, but rather it is a process wherby we
pivot from those decisions, actions, or
feelings and redirect our priorities, focus, and
choices.
In the process of teshuva, regret isn’t merely
an emotion, it is a dynamic process whereby
we replace the remorse-worthy act with an
active commitment to “remove the mark” of
that mistake currently embedded within us.
It was 2005. At 53-years of age, Eugene
O’Kelly was full of life. As the chairman and
CEO of KPMG, one of the largest U.S.
accounting firms, O’Kelly was the
consummate global jet-setter. His successful
career brought him into the presence of
Warren Buffet and other business giants.
Gene spent days, nights, and weekends
planning the firm’s continued success. He
described himself as feeling, “vigorous,
indefatigable, and … near immortal.”
In the spring of 2005, Eugene’s wife,
Corinne, noticed that the right side of her
husband’s face was sagging. He went to see a
neurologist and within a week, Gene was
diagnosed with inoperable, late-stage brain
cancer. He was given three months to live.
With this sudden and shocking diagnosis,
Gene had to quickly determine how he would
spend his remaining 100 days on earth. He
made an immediate decision to make every
minute of his life count.
Gene wrote that he wanted “every calculated
step to be filled with truth of purpose.” Gene
struggled to live in the moment as he began a
process he called “unwinding.” Bidding
farewell to friends and loved ones not only
spurred Gene to recall happy memories but
kept his “focus on life, not death.” They
guaranteed that he was “almost always
thinking about what mattered.”
For those considering taking the time
someday to plan their final weeks and
months, Gene had three words of advice:
“Move it up!”
The gemara in Shabbos (153a) says:
רַבִּי אֱלִיעֶזֶר אֹומֵר–: ׁשּוב יֹום אֶחָד– לִפְנֵי מִיתָתֶָך.
שָׁ אֲלּו תַּלְמִידָיו– אֶת רַבִּי אֱלִיעֶזֶר: ו ְכִי אָדָם יֹודֵעַ –
אֵיזֶהּו יֹום י ָמּות? אָמַר לָהֶן: ו ְכׇ ל –שֶׁ כֵּן, י ָׁשּוב הַּיֹום,–
ׁ.שֶמָּא י ָמּות לְמָחָר–, ו ְנִמְצָא כׇ ּל י ָמָיו בִּתְׁשּובָה
Rebbe Eliezer says “Repent one day before
you die.” His students asked him: “But does
a person know which day he will die?” He
responded: “Therefore he must certainly
repent today, for maybe he will die tomorrow
– in this manner all his days are spent in
repentence.”
Don’t wait to unwind your life – move it up!
Tell friends who have enriched your life,
thank you. Ask those whom you have hurt or
disappointed for forgiveness. Identify your
regret, reframe it, extract a lesson, and make
a correction by redirecting yourself.
Gene did one more thing in those last three

months — he wrote a book called “Chasing
Daylight.” It’s a moving and humbling
narrative describing Gene’s search for a
better way to die. He opens the book by
saying, “I was blessed. I was told I had three
months to live.” He writes that he worked
hard so he could spend retirement with his
wife — a goal that suddenly vanished with
his diagnosis.
Chazal tell us that on this sacred day, Sifrei
Chaim and Sifrei Meisim, the book of life
and the book of death, are open. We typically
think of Hashem sitting before these great
ledgers and determining where to put our
name. However, the Koshoglover, Rav
Aryeh Zvi Frimer, writes in his Eretz Tzvi
that Hashem isn’t the only author in these
books. On this special day, we decide what
we want to write into the book of death,
things that we want to let go of, destroy, put
behind us. And we decide what to write in the
sefer ha’chaim, what we want to give life to,
learn from, grow from and build a future
from.
Regrets guide us in this editorial process as
we choose the relationships, habits, and
experiences that need unwinding and those
that we need to lean into in order to lead a
meaningful life. Regret is not a time machine,
we can’t undo the person, parent or spouse
we were, but we can still determine the
person we will have yet to be.
Gene spent many precious hours writing his
book fully cognizant of his fundamental
limitation — he would be unable to write the
final chapter. In finishing the book that her
husband began, Gene’s wife, Corrine,
reflected on how Gene was so concerned
about how to say goodbye to their teenage
daughter: “He worked so hard to find the
perfect trip or gesture or gift for her to have
the rest of her life… but how is that ever
possible? How do you unwind a relationship
with your child who is only 14?”
In his final days, Gene had one profound
regret: “Had I known then what I knew now,
almost certainly I would have been more
creative in figuring out a way to live a more
balanced life, to spend more time with my
family.”
At the end of the experiement in Manhattan,
the researchers wiped the chalkboard clean
and wrote “Clean slate” across it. Today, we
aren’t writing regrets on a chalkboard but as
we feel charata, we can practice charita –
engraving our regrets on our hearts as we
klop al cheit shechatanu lefanecha. If we
properly edit our books of death and of life
and pivot accordingly, at the end of today,
we, too, get a clean slate, a fresh start, as
Hashem promises us: Salachti Kidvorecho.