Teshuvah Beyond the High Holidays

A man walks into a bar and orders a shot of whiskey.

He swallows the whiskey and immediately throws the empty glass at the bartender’s face.

The bartender is furious. The man begins apologizing profusely. He says he does not know what came over him. He begs for forgiveness and asks for another drink.

The bartender reluctantly pours him another shot.

The man drinks it and, once again, throws the glass directly at the bartender.

This happens several more times until the bartender finally loses his patience, throws the man out, and tells him not to come back until he has dealt with his problem.

A full year passes.

The man returns to the bar and orders a whiskey. He finishes the drink and promptly throws the glass at the bartender.

The bartender stares at him in disbelief.

“I thought you took care of your problem!”

“I did,” the man replies. “Now I’m okay with it.”

It is a good joke because it touches on a serious question: What does it mean to make peace with ourselves?

Does teshuvah mean learning to accept our misdeeds? Does it mean coming to terms with them? Or must we live with guilt, continually berating ourselves and stewing in the misery of our failures?

We sometimes imagine that the more terrible we feel, the more sincere our teshuvah must be. If we remain miserable long enough, perhaps that proves that we really understand what we did.

Chassidus offers a more demanding and ultimately more hopeful approach.

Earlier generations of Chassidim sometimes practiced forms of asceticism. They fasted, deprived themselves of physical comforts, and used bitterness as a way of breaking through the hardness of the heart. For those people, in those generations, this could be a necessary part of their avodah.

The Rebbe teaches that this cannot be the central path of teshuvah for our generation. In the maamar Margela B’pumei D’Rava, the Rebbe explained that the deliberate cultivation of bitterness is no longer the avodah our generation requires. Our path must emphasize bitachon, positive action, Torah, mitzvos, and simcha.

This does not make teshuvah softer or less serious. It changes where we place our energy.

Regret can awaken us, but it cannot be where we live. Guilt may tell us that something needs to be repaired, but guilt itself does not make the repair. Feeling terrible is not the same thing as becoming better.

Just before the conclusion of Rosh Hashanah, a man from shul came over to speak with me. He happens to be a psychologist and a coach, and he told me about a book he was reading. One of its ideas was that thinking positively about oneself can make positive change more likely. When people continually beat themselves up and focus entirely on their negative qualities, they often find themselves repeating the very behaviors they are trying to escape.

The conversation stayed with me.

There is something deeply Chassidic in that insight. Chassidus teaches that the mind can guide the heart. When we use our seichel, our intellectual faculties, to direct our thoughts with clarity and purpose, we can begin to change our emotional and behavioral patterns as well.

This is not positive thinking as denial. It does not mean pretending that we did nothing wrong or excusing the pain we caused. Teshuvah demands honesty. When another person has been harmed, it demands accountability, apology, restitution, and changed behavior.

But accountability and self-hatred are not the same thing.

In my own experience, teshuvah brings guilt, shame, and regret. Those feelings are real, and perhaps unavoidable. They can force us to confront parts of ourselves we would rather not see. But they are intensely personal feelings, and they cannot become the substance of our entire spiritual lives.

The real avodah begins when we decide what to do with them.

Can I acknowledge what I did without deciding that it defines everything I am? Can I remain accountable without surrendering to despair? Can I believe that I am capable of becoming better, even when I have evidence of my capacity to fail?

There is a crucial difference between accepting what I have done and accepting it as something I will continue to do.

The man in the joke learned to feel comfortable throwing glasses. That is not teshuvah. Teshuvah would mean recognizing the damage, apologizing to the bartender, paying for the broken glasses, and then learning how to put the next empty glass quietly on the bar.

We are now in the Aseres Yemei Teshuvah, the Ten Days of Repentance between Rosh Hashanah and Yom Kippur. These days ask us to look honestly at our lives. But honesty does not require hopelessness.

Perhaps the highest form of teshuvah is the decision to believe that we are more than our worst actions, while accepting full responsibility for them.

That belief is not an escape from accountability. It is what makes accountability sustainable. If I believe that failure is my permanent identity, there is little reason to struggle against it. But if I believe that my deepest self remains connected to Hashem, then change is always possible.

Teshuvah, then, is not a moment of guilt confined to the High Holidays. It may not even be a process with a clear beginning and end.

It is an entirely new approach to living.

It is the practice of telling the truth, making repairs, and choosing differently. It is refusing to confuse remorse with paralysis. It is drawing closer to Hashem with the confidence that no matter how far we have wandered, the road home remains open.

And perhaps that is why the deeper teshuvah must be done with simcha. The joy does not come from what we did wrong. It comes from discovering that we are still capable of returning.