Why Do We Say Vidui on Erev Yom Kippur?

Something about Erev Yom Kippur seems really out of place.  

Let me explain.  Over Yom Kippur, we said vidui, the confession of sins, nine times.  But what seems out of place is that one of those times is during Mincha before we eat our final meal before Yom Kippur.  

We don’t shake our Lulav before Sukkot.  We don’t eat matzah on Erev Pesach.  In fact we’re forbidden to eat it before the Seder.  So why are we performing the essence of Yom Kippur before the holiday even starts?  

A common explanation is that we say vidui before Yom Kippur in case something unexpected happens, like choking on a bone at our meal and not having said vidui even once. 

But why is Erev Yom Kippur different from any other day? After all, the unpredictable can happen at any moment.

The difference is what we’re about to do. We are on the cusp of something incredibly powerful. 

The Satan knows this. 

The closer we get to a moment of profound spiritual growth, the harder the Satan works to stop us. And on Erev Yom Kippur, the stakes couldn’t be higher. 

The Satan Attacks When the Stakes Are High

The teshuva, the repentance, we do on Yom Kippur has the power to change worlds. The Satan knows that, and since he has no power over us on Yom Kippur itself, he throws everything he’s got at us the day before. The Gemara (Yoma 20a) states that the numerical value of השטן – hasatan is 364—one day short of a full year—because on Yom Kippur, he is powerless.

This struggle isn’t unique to Yom Kippur. It happens before every big spiritual moment. 

Erev Shabbat is often filled with stress and frustration because the Satan works overtime to diminish the peace and joy of Shabbat. The bigger the opportunity for holiness and greatness, the more resistance we feel.

My Personal Struggle

I feel this on a personal level too. I believe deeply that Hashem has huge plans for me.  This journey I’m on that I’m sharing through my content, is leading to something huge. 

It hasn’t been easy. For a long time, I thought that my struggles might have been a direct result of my past mistakes—that the suffering I experienced was a necessary part of my atonement.

In Gemara (Yoma 86a), we learn that different types of sins require different levels of atonement based on how serious they are. For example, if someone violates a positive commandment, doing teshuva is enough to be forgiven. But for more serious transgressions, like breaking negative commandments, it can take more—sometimes teshuva and Yom Kippur together, and in some cases, even suffering is needed to fully clean the slate.

I used to think that this might have explained everything I was going through—that my pain was part of my necessary journey of teshuva.

I think of the story I previously shared of Rav Saadiah Gaon visiting an inn away from his home and learning the lesson that each day as he got closer to Hashem made him realize that he didn’t treat Hashem properly on previous days and needed to do teshuva for it.  

Maybe I was hard on myself.  Maybe too hard.  Maybe it was all in my head.  

Hashem Forgives Us When We Knock

Hashem is full of mercy.  We just said on Yom Kippur the beautiful piyut of  “V’chol ma’aminim”, where we say that Hashem is “הַפּוֹתֵחַ שַׁעַר לְדוֹפְקֵי בִתְשׁוּבָה” – Hashem opens the gate to those that knock in teshuva.

It hit me this Erev Yom Kippur: Hashem forgave me a long time ago. 

But even though Hashem had forgiven me, on some level, I hadn’t forgiven myself. I was holding myself back. I was letting the Satan’s voice keep me from moving forward, from stepping into the life I’m meant to live.

Maybe It’s Us…

I’m not alone in this. How many of us carry around guilt, blame, and regret long after Hashem has already forgiven us? 

We tell ourselves we’re not good enough, that we don’t deserve to live joyful, fulfilling lives. Instead, we get stuck in cycles of anxiety and self-doubt. 

But that’s not the truth—that’s the Satan speaking, trying to stop us from reaching the great things Hashem has planned for us. As we said earlier, the Satan works hardest when we’re on the verge of something big, and this is no different.

Let’s Forgive Ourselves

It’s time to stop letting the Satan win. It’s time to forgive ourselves.

The Ramchal teaches in Mesillat Yesharim that after teshuva, we are meant to serve Hashem with joy—Simcha. But how can we serve Him fully if we’re weighed down by guilt? 

Teshuva wipes the slate clean—so shouldn’t we do the same for ourselves? If Hashem has already forgiven us, we need to let go of that guilt.

Just like Ya’akov Avinu fought the Satan before receiving his new name, Yisrael, we too must confront that inner voice that tries to convince us we don’t deserve happiness. The greater the potential, the stronger the resistance. It’s time to face that voice head-on and show the Satan the door.

Hashem Sees the Greatness Within You

Hashem believes in us far more than we believe in ourselves. Hashem sees the greatness within each of us. It’s time we start seeing it too. 

Yes, there’s a time for regret, a time for teshuva—three times a day in fact.  For the short moment in the Amida when we beat our chest and ask for forgiveness with the words “סלח לנו אבינו כי חטאנו” – “Forgive us Father for we have sinned”.

But beyond that, it’s the Satan who tries to drag us down and convince us that we don’t deserve to be completely joyful. When we’re weighed down by guilt or sadness, how can we serve Hashem with our full heart?

The tochecha – the curses for not following Hashem – we read just a few weeks ago teaches us that one of the reasons we were punished wasn’t for not doing mitzvot, but for not doing them “בְּשִׂמְחָה וּבְטוּב לֵבָב” with joy and a full heart. Hashem doesn’t just want our service—He wants our service to be full of joy.

Now, Let’s Enter Sukkot Filled With Simcha

So as we leave Yom Kippur, and approach Sukkot, the holiday of Simcha – joy, let’s commit to taking our teshuva to the next level.  Let’s commit to forgiving ourselves, to letting go of the guilt that no longer serves us. Let’s commit to seeing the greatness Hashem sees in us and to living joyfully, fully embracing the life we’re meant to live.

Sukkot is a time of pure joy, a time to bask in the closeness we’ve built with Hashem over the past 40 days. Let’s carry that joy forward and use it to fuel the amazing things Hashem has in store for us.

Forgive yourself.

Show the Satan the door. 

Be B’simcha, serve Hashem, and step into the greatness you were put on this earth to achieve.