Teshuva Re-examined

It’s not fixing what’s broken. Rather, it’s coming back to our true selves in our relationship with Hashem.

Elul. Teshuva. They are words that stir up a whirlwind of emotions in many of us; or, if we’re being honest, sometimes they stir up nothing at all. What are we really supposed to be doing this time of year? Should we be feeling scared? Timid? Regretful?

For me, one question always stood out: What’s the point?

We go through the motions every. single. year. We promise not to repeat our mistakes, we rehearse the four steps of teshuva our teachers drilled into us, and then…we wait for the last shofar blast of Yom Kippur, holding our breath until the whole uncomfortable mix of guilt and pressure finally passes. Then we can move on to the “good stuff”—decorating the sukkah, dancing, celebrating.

But if we know we’re just going to slip back into our old patterns anyway, does teshuva even count?

What’s the point?

A few years ago, I came across an answer that completely reframed this for me, and it’s one I return to again and again.

Look at the word teshuva. Lashuv. To come back.

We often think of teshuva as “repentance” or “penance,” but those are actually Christian concepts. The Hebrew root—lashuv—means to return.

And here’s the biggest misconception out there: Yiddishkeit is not a religion.

Take a minute to let that sink in. And yes, I know- I just jeopardized years of Bais Yaakov education. But stay with me.

Yiddishkeit is not a religion. It’s a relationship.

It’s our relationship with Hashem. In fact, our sole purpose in life is to nurture and nourish the deepest connection to Him that we can.

And in a world full of illusion, dichotomy, and distraction, it’s so easy to forget that. Just like in any relationship (marriage, anyone?), we forget why we began in the first place. Who we’re in relationship with. And why this connection matters so deeply.

So Hashem gave us a gift: teshuva–the ability to return, to come back to closeness. That’s why the concept of teshuva was put in place even before sin existed (another Christian word, by the way)—because closeness was always the goal.

Now, about those four steps we all learned. Yes, there are four parts to noticing where the crack in the relationship appeared and making a commitment to repair it so we can stay close going forward.

But let’s look at the word a bit more closely. Teshuvah. Tashuv and the letter Hey. Come back to hey, to five. What does that mean? We only talk about 4 steps, where’s the 5th?

The number 5 is pretty special. It’s a number that represents coherence, wholeness, and the human-divine connection. 

We have the Chamishei Chumshei Torah, the five levels of soul, the five senses, the five expressions of redemption. 

What these all have in common, is that they represent a unity and cohesion amongst them. And what’s more, we often find that it is a fifth element that binds and completes a set. 

Like four legs that are useless without the seat that creates the chair, or the four posts that are meaningless without the talis that makes the chuppah. Or your four fingers that are helpful but your opposable thumb that is the real deal breaker. 

So, if teshuva asks us to return to this truth; the secret of five, there must be more to it than just the 4 part process we’ve always known.  

The “fifth” element is the step that binds the other four together:

It’s about asking ourselves the question:

Why did I do this in the first place?

What was really going on? What was I needing? What did I hope to gain by acting that way? How is my relationship with Him doing?

We already know what we’re supposed to do or not do. The question is deeper: What drove me in that moment? How can I understand myself better so that I don’t need to repeat it again?

“Da Es Atzmecha”, know yourself–it’s not just a nice idea meant to make us feel good. It’s real. If we don’t take the time to know ourselves intimately we will keep stumbling over the same trip points and keep wondering how we got there. 

That’s teshuva. Not a cycle of guilt and release, but a return—to Hashem, to ourselves, and to the essence of the relationship we were always meant to nurture.

So, how to go about this?

The real truth is, it takes time, intention, and mindfulness to really integrate an idea like this. But, what if we could simplify it to help us begin. To make that first step just a bit easier. 

Think of something in your life you would like to work on. A trait, a behavior, a belief, something you would like to see shift and create more connection between you and Hashem. Once you have that, try these five steps (of course it has to be five!).

Step 1—Clarify

What does this particular aspect of your life look and sound like? How do you act, what do you do, what do you say? In what way does this have an impact on your life—in a very literal sense. If somebody else was watching you, what would they see/hear etc. Describe this in as much detail as you can. 

Step 2—Introspection

When you consider this, what does this make you think about yourself or your life? What does it make you believe about yourself or your life? (this can be something like—I am…., I should…, I am not…, I am so…, my life/spouse/kids/family is…., life is….., or anything that comes to mind (there is no right or wrong answer here).

Step 3—Feel

Take a few minutes of quiet (Yes–I know what time of year it is!) and consider these thoughts and beliefs. Notice what you begin to feel in your body as you consider this.  Is it an emotion? A sensation? Numbness? Whatever it is that comes up for you, write it down (or record it in a voice note), and any details that you notice (like the name of the emotion, where in your body you feel it, how strong/weak it is, what quality it has, etc.). 

Step 4—Dream

When you stop and take time to get to know yourself better, underneath the thoughts, the beliefs and the emotions, what is it that you truly desire for yourself? At its essence, what are you hoping for? If you weren’t held back by anything, or limited by anything–what do you most desire? 

Very often this will be something simple and basic yet profound. Like acceptance, or love, or support. 

Step 5—Consider

When you’ve found your desire, allow yourself to consider with honesty:

How does my current way of doing things benefit me and does it truly help me achieve my desire? Even when we self-sabotage there is always an upside somewhere in the bargain, and very often, until we don’t know what that is, it’s hard to move on to something else. We don’t even realize that we aren’t ready to lose out on whatever benefit the current state of affairs offers us. 

Is there a  better way or other way for me to do things that will invite this desire into my life–perhaps in an even stronger way? And if I’m successful, how will my life benefit from it? What will be different? 

How’s that for getting to know yourself better? Isn’t it different when you take the time to understand who you are and where you’re coming from. Now, I already know what your next question is–but, what do I do now?

And the answer is–nothing. You’ve already done it. You know now. This awareness will escort your movements now, and don’t be surprised if you find yourself thinking about it here and there. Or when you’re about to make a decision. Or while you’re peeling the vegetables for that one more extra side dish. 

You’ve completed something magnificent–a process of return to the One who loves you more than you understand what love even is.  And that’s the beauty of teshuva. It isn’t about climbing a mountain in one day or reinventing ourselves overnight. It’s about coming back—slowly, honestly, tenderly—to who we truly are, and to the One who already holds us there. With every step of awareness, with every layer of honesty, we return. Not with guilt. Not with pressure. But with love, with curiosity, and with the quiet knowing that we are never too far to come home.