I recently asked a congregant to share a personal reflection during the High Holidays. The response:

“Rabbi, when I examine myself, I realize that I come up with the same short comings year after year. It’s not that I don’t see any improvement at all, or that I have unrealistic expectations.

I just experience myself struggling with the same exact issues every year. And of course, they all have to do with interpersonal relationships— how can I be a better mother, a better wife, a better friend. It gets…disheartening.”

Erev Rosh Hashanah 5772

I’m sure each of us can relate to this struggle.

A year ago, we probably acknowledged the same frustrating missteps,

resolving not to repeat them.

Now, as we discover that we have similarly missed the mark,

do we again pledge not to err in the future?

In a year’s time, will we stand once more before the Eternal,

in this moment of introspection, and confess precisely the same lapses?

These questions and mounting impatience with ourselves goad us to define the Jewish concept of chait, or error.


Understanding our chataim, errors, is part of our process of turning inward,

bettering ourselves and our relationships: teshuva.


Every time chait appears in the Tanakh, it means “off target,” “missing the mark,” “mistake,” and “unintentional error.”

A chait is not intentional wrongdoing. A chait does not imply eternal condemnation.

A chait does not require endless guilt.

In the Book of Judges, shooters from the tribe of Benjamin are described as being so good with their weapon that they can “aim at a hair and not chait.[1]

The text means to aim at a hair and not “miss,” i.e., not land off target.

Another example comes from the Book of Kings. King David is on his death bed.

His wife, Bathsheba, comes to him saying, “If Solomon does not become king after you, then Solomon and I will be chataim,[2] meaning that Solomon and Bathsheba will not measure up, will not reach their potential.


Being “off target,” “not reaching the mark,” “mistake,” and “not reaching potential”

all distinguish chait from “sin.”

The Jewish response to those chataim, errors, is teshuva—turning and returning.

Turning inward, examining our thoughts and deeds, so we may return to our truest selves.



Maimonides, our great medieval theologian and philosopher declared,

“A person should TRY to perform teshuva…”[3] Try??! Isn’t teshuva is a mitzvah,

a commandment, and not merely a recommendation?

Maimonides is referring to a specific type of teshuva

a comprehensive effort to improve one’s attributes,

not just focused repentance for individual deeds.

Maimonides is wise enough to make this an invitation, not a demand.


Teshuva for chataim is also addressed when the prophet Yeshayahu, Isaiah, declares, “Let the one lost from their path abandon their way,

and the iniquitous person their thoughts. “[4]

When repenting, we can disown our misdeeds,

and even our thinking to change our life’s direction, to forsake the path of our mistakes.


Repairing character flaws and changing the course of one’s life – these big undertakings are what Maimonides urges us to “try.”

In Judaism, the endeavor is critical.

A person’s efforts to achieve righteous conduct have status and value.

Intention is the first critical step in teshuva.

This energy, not just the result, is a moment of holiness in our tradition.  

Abandon self-criticism for a new path to follow.

The focus of teshuva is not a result, but rather the adjusted path, the aspiration, the effort.


Once we observe ourselves realistically and commit to trying,

where do we go from there?

First, we recognize our misdeeds and make a wholehearted resolution not to repeat them. This decision implies knowing the more desirable path from the less desirable one.


But how can we, realizing that a habit is deeply ingrained, resolve not to err in the future, when experience shows clearly that we will likely lapse again?

Contemporary Rabbi Dovber Pinson teaches that remorse over the past

indicates an acute awareness engraved upon our hearts.

The Hebrew word charatah, “remorse,” is related to the word charitah “engraving.” Once remorse is engraved,

we stand a better chance of not forgetting our history and slipping.

Our deeds and engraved remorse enable us to choose wisely in the future.[5]

Rav Pinson may be optimistic about results,

but his comment also shows Judaism’s high regard for even initiating teshuvah.


There are two ways to raise the probability

that teshuva will follow remorse and impel us to change.

First, articulating what went wrong in the past and verbally committing to change in the future.

Speaking clarifies our thoughts, crystallizes and structures them.[6]

Articulating those conceptions unveils a deeper understanding.

Thoughts solely in the mind remain elusive and unstructured.

However, when we are able to declare these same thoughts, they become more coherent.


As Rav Pinson continues, not only do thoughts become clearer and more defined when spoken aloud, they create our reality.

The human mind depends on language. Something verbalized is more real.

The spoken or written word enables our thoughts to attain permanence.


We have eight days remaining until Yom Kippur. How can we voice desires for teshuva? We might confide in a respected friend or family member,

or speak to the Eternal through prayer. We might write a list or a letter.

                                    *           *           *           *

The second way to make teshuvah is called teshuvat ha’geder

literally teshuvah “of the fence.”

We erect additional barriers, restrictions on our behaviors,

so that we may not be tempted to transgress.

We set guidelines so that we will not inadvertently cross over the line and fail.

For me, the absence of teshuvat ha’geder explains why we return to the same struggles each year.

We find ourselves with the same teshuva each High Holy Day season

because we fail to build the fence.  

We are so plugged into technology—

to our Smartphones, to email, IM’ing, GChat, Twitter, Facebook, Linkedin.

We don’t have time to reflect, to connect with our best selves,

the individuals we commit to be each High Holiday season.

Whenever I ask someone how they are, they say, “Good, but busy.”

We are not a society that champions reflection and wholeness.

Those rewarded put in 80 hour weeks, never see their families,

and bring their Blackberries on vacation with them.

And I am just as guilty of this. My Smartphone charges by my bed.

First thing in the morning, right after I say Modah Ani, I look to see who has emailed,

my ticker tape to-do list already spinning through my mind.

Perhaps, we return to the same teshuva each year

because we have not made time to connect with our souls.

How can we challenge existing character flaws?

How can we make time for what is important?

How can we nurture ourselves and create new paths?


Teshuvat ha’geder. Building a fence for ourselves,

so that we are less tempted to transgress.

What would it be like not to check our phones during dinner?

Not to look at work email once we’ve left the office?

With all these externals claiming our attention, we need “muscles” to resist.

It requires healthy boundaries, but how powerful to be truly present with others, with ourselves?


The other day I was on a walk, strolling with a friend around Greenlake.

She mentioned a good restaurant she had been to, and I asked where it was.

Immediately she whipped out her Iphone to look up the address.

In that moment, the character of our time together changed completely.

It wasn’t about the sunshine on our faces, the baby ducks paddling through the water,

the simple joy of shared conversation without intrusion.

Her phone didn’t have a good signal. She fiddled with it as we walked.

The glare of the sunlight obscured the display.

Instantly, our time became about the phone, instead of about each other.

                                                            *           *           *           *

Each week we have an opportunity to practice teshuvat ha’geder…Shabbat.

Twenty-five hours to reflect on the person we were this week

and the person we seek to be.

Twenty-five hours specially devoted to enjoying family time,

to making a day of menucha, rest, for ourselves—setting aside time for kedusha, holiness, by simply being.

Not creating, not rushing, not dominating. And it’s so hard. I know; I’m a do-er.

It’s a great challenge to just be. Not to think about what comes next; not to think about how to be more productive,

not to puzzle over all our responsibilities demands a strong fence.

What would it be like give ourselves the gift of a true Shabbat?

                                                            *           *           *           *

If once a year on the High Holy Days is the only time we practice teshuvat ha’geder,

we will probably be unsuccessful. We will likely return to the same chait each year.

We will not have the muscle to do teshuva.

If we want to build our teshuvat ha’geder, this is the time.

What fences do we need, to be wholly connected to our truest, most beautiful selves? How can we sanctify the precious time we have?

                                                            *           *           *           *


Elijah finds God in the still small voice.

God is in the quiet, in the stillness, in the “just being”

because we are most receptive in silence.

In those moments of reflection we exclude the intrusions outside us.

Moments of perception won’t just happen without kavana, intention.

We have to give ourselves and our loved ones this time and protect its sacredness.


Resist becoming disheartened.

Resist being daunted by the process of teshuva.

Teshuva itself is about optimism and genuine opportunity.

We have the power to reorient our moments

and to overcome external obstacles and old habits.

Rosh Hashana is a gift.

We liberate ourselves from the past and begin anew.


L’Shana Tova Tikatavu.


[1] Judges 20:16.

[2] I Kings 1:21.

[3] Rambam, Hilkhot Teshuva 7:1.

[4] Isaiah 55:7.

[6] https://iyyun.com/teachings/practices/the-way-of-teshuvahreturn.