Teshuvah (תשובה) means turning yourself around. Recovering. Realigning. Getting back to who you truly are, to your inner soul, to the purpose for which you were sent to this world. And yet higher.

Teshuvah is often mistranslated as “repentance.” That’s misleading. You can repent and never do teshuvah, just as you can do teshuvah without repenting.

Repenting means feeling you are bad and that the only way to become good is by punishing yourself. You could sit in such penitence and self-affliction your entire life.

Teshuvah means you recognize that the person you’ve become is not the real you. The place you’re stuck is not where you belong. You are good, this place is bad. So you turn yourself around and reclaim your true place and your true identity. You behave, think, and feel differently. You transform.

Remorse for the past helps you do teshuvah, but it’s a very different sort of remorse than repentance. If the remorse of repentance is a persistent ache, the remorse of teshuvah is a hot spice to a delicious dish. It’s not a place where you get stuck. It’s something that pushes you further ahead.

Teshuvah and Purpose

We can’t explain teshuvah without explaining purpose.

Everything the Creator made, He made with purpose. He doesn’t program his creations with an algorithm, as we do. Rather, each creature emerges out of His wisdom with a particular nature, a soul, and a body, all in sync with the purpose He has in mind.

Water flows. Fire burns. Wheat stalks produce kernels of wheat, while date palms produce dates. Sheep graze on grass, while wolves prey off sheep. They all follow their nature to create one, grand, divine symphony, each one playing its vital part without a single extra note.

You are the exception. You are a human, endowed with a very peculiar sort of intelligence and self-awareness. Following your natural urges and instincts alone is a road to self-destruction. You are meant to know your nature and transcend it, to engage your human oversized brain in the task of alignment with your divine purpose.

That gives you a great advantage over all the other creatures. They do what they do because that’s what they were created to do. You fulfill your purpose out of a deliberate choice. That puts you in an intimate bond with your Creator, a partnership, a deep relationship with the infinite, loving Creator of all things.

That’s why humans like you are the only creatures that can actually improve on this amazing creation and bring it to its ultimate fulfilment.

Psyche Alignment

How do you know you’re on track—that you’re aligned with your purpose in life?

Because the Creator, in His infinite kindness, transmitted our instructions to us through Moses at Mt. Sinai. And He continues to send us wise men and women, pure souls, to guide us along that path.

In His Torah, He tells us what we need to do, to speak, and to think about. He teaches us what attitudes to acquire—like humility, optimism, happiness, patience, and concern for others—and what attitudes to avoid—like arrogance, pessimism, sadness, anger, and callousness to others.

What if you get off track? You get back on track—and do all you can to catch up and fill in what you missed while off track. More importantly, you learn from your mistakes so that you won’t fall back off track again. You do teshuvah.

That may sound simple. Until it isn’t. Because here’s the snag:

When you get off track, your whole psyche falls off track—your mind, your emotions, all of it. In fact, it’s your mind and heart that took you there. You’re like the sheep who has discovered the neighbor’s garden, or the lion who has tasted human flesh. You’ve been rewired.

That’s a problem, because, left that way, your mind and heart can no longer be trusted to keep you on track. In fact, they will keep taking you off track if you follow their directions.

So your teshuvah can’t be about action alone. It has to be filled with action, words, and cognitive immersion that reach back into who you are, how you think, and what feelings come out of those thoughts. Just as the bad track infected all those things, so the good track has to reach even deeper to wipe them clean.

But that’s also not so simple: You can’t just switch back to how you were before the mess. There’s no return. You have to switch back to something way beyond that.

The basic rule of teshuvah, then, is: If you fall down, bounce back higher.

How to Do Teshuvah

A man came to Rabbi Menachem Mendel of Kotzk. He told him, “Rebbe, I sinned!”

The Kotzker told him, “So do teshuvah!”

The man said, “I don’t know how. I have no one to teach me.”

The Kotzker asked, “Did you know how to sin? Did someone teach you?”

“No,” said the man. “I didn’t need anyone to teach me. I just did it.”

“So just as you sinned, in the same way, do teshuvah,” replied the Kotzker.

How you fall off, in the same way, you get back on. No one just slips off the track—you get pulled there seeking gratification. All living things seek gratification, and when they get it, they absorb that experience into their repertoire. We call that “learning.” Your brain, your nervous system, your muscles, and more, all learn a new stimulus-response.

Now, you have to put that process in reverse. You need to reset your stimulus response.

There’s two elements involved here: Pain and pleasure. That makes for two possible routes back:

One route is to switch out your newly acquired pleasure-response node for pain. That’s the remorse-route. Remorse rewires your system to associate that stimulus with pain rather than pleasure. Some classic works of Jewish ethics (called mussar) appear to be suggesting this route.

Then there’s the pleasure route: You replace one pleasure with a different, deeper pleasure. You put your head in a good space, filling it with lots of inspiring thoughts, stories of tzadikim, wisdom-teachings, and inner Torah. You contemplate these deeply. And you carry them into action.

Eventually, you’re so enraptured by this experience that any reflection on the culprit stimulus is painful—because you feel it’s blocking your total immersion into this new, beautiful mindspace.

This is the route the Rebbe directed people towards in many letters and in public talks. As you can see, the pleasure-route also involves pain, but only as a spinoff. It’s not the focus. That’s key.

Because when pain is the central focus, you’re putting yourself at peril. Your head is in a dark and gloomy space. You’re thinking about bad, not good. It’s almost inevitable that you’ll start thinking about why you did the things you did—and how much pleasure you derived from doing them. Instead of pulling yourself out of there, you’re in danger of pulling yourself further in.

The pleasure route of teshuvah, on the other hand, is like a ride in a hot air balloon. You sail upward to a magnificent, panoramic view. You crave for more, a yet greater vision. You realize there’s weight on board that’s holding you down. So you toss the sandbags overboard. And you soar higher.

So too, when you put your head in a good space, you feel pulled towards the light—and with the ecstasy of that pull comes excruciating pain. Your tears erase the muck and grime that conceal the light—and you open your eyes to find yourself within its very origin.

That’s the real teshuvah, because it’s a route of self-transcendence, leaving that false self that did those ugly things behind. You’re fresh and clean in your Creator’s eyes—because you are no longer the person that did those things. You can’t be held accountable for things you never did.

Don’t Regret Your Sins

This is a common trap. There’s a major misconception out there that teshuvah is all about regretting what you did and resolving not to do it again. That’s absolutely not so.

Imagine someone insulted you at a public meeting. They apologized, saying they will not insult you again at a public meeting. Umm—is everything okay now? Or is there something vital still missing?

Like, why did they do that? Where is that attitude coming from? Has that been resolved? Or is it just going to surface in some other altercation?

The same applies between you and G‑d. You don’t do teshuvah for what you did, but for why you did it. Imagining otherwise can get you in worse trouble than you started with.

For one thing, why are you regretting what you did? Is it because you feel stupid for doing it—that a bright guy like you shouldn’t do something so dumb? All you’re doing, then, is reinforcing your ego—which was the principal culprit that got you into this mess to begin with.

Or maybe you’re afraid of the consequences—that people may find out about what you did and not like you. Or you figure that G‑d knows about this and is going to get you for it.

Either way, you’re not really regretting what you did—if the consequences wouldn’t be there, you’d be fine with it.

So, no, teshuvah is about who you were at the time. You went in the opposite direction than your Creator intended and became the opposite of who you really are. That’s what needs to be fixed.

You don’t do teshuvah when you say, “I was bad for doing that.” You do teshuvah when you say, “I have a wonderful partnership with my Creator. We have an amazing bond with one another. He trusted me to do my part, and I trusted Him to stand with me every step along the way. How could I possibly have pulled myself away from that bond and that partnership? How could I bear to stay apart even one more moment?”

And in that moment, you’re back with Him again. He was waiting for you all along.

How Long Does It Take?

As soon as you reach that complete resolve, that sense of “I can’t bear another moment of separation,” you’re back again.

But then there’s stuff to fix. There’s soul-cleansing to do. There’s catch-up work. The system needs rewiring. Behaviors have to be relearned. That takes time.

G‑d helps. “Open to me just a pinhole,” He says, “I will open up to you like the entrance to a great hall.”1

He helps by placing challenges in your life. These are your teachers, your friends, and your scrub-team. If you accept them with love, that accelerates the process by orders of magnitude.

He helps by giving you Yom Kippur. You experience a little hunger. You stay in shul for a day. You say the al chet (“for the sin that I did before You….”), because saying to G‑d out loud how you turned away from Him is a great way to throw those sand bags overboard. And you sing songs of love and longing to Him. If you do it right, you come out transformed and cleansed.

He helps by providing you opportunities to help others. You accept by giving large amounts of tzedakah. Few things cleanse the soul as does tzedakah.

And He helps by giving you a new heart and a new mind in which the words of Torah can shine and illuminate your path to Him.

The Unfair Deal

Then there’s the unfair part of teshuvah: The guy who messed up ends up in a place the guy who always stays on track can never reach to.

How does that work?

It works because you don’t really understand where you’re going and you haven’t really touched your innermost self until you’ve fallen off the track and gotten yourself back on. Ask a recovering addict. Ask the guy who hit rock bottom and pulled himself up from there—with a little help from his friends and a lot of grunt work from himself.

You get in touch with your inner fuel. Beforehand, it was habit. It was what your parents and teachers taught you. It was what your community did, and so you did it too. Now, it’s you doing it, you from the very core.

And you have the power of all those ugly messups. You have that precious memory of how distant you placed yourself, how you ripped yourself away from the most valuable thing you could possibly have—your intimate bond with your G‑d. It’s a precious memory because it snaps back like a cosmic-size elastic band, catapulting you into a whole new orbit, a whole new intimacy with the divine.

Indeed, someone who does teshuvah and now does mitzvahs just like any tzadik who was always on track is wasting all those juicy sins.

Teshuvah for Tzadikim

Nevertheless, to you tzadikim out there who never failed we say: there is still hope. The Zohar says that Moshiach will come to teach the tzadikim to do teshuvah.2

Because, in truth, all of us are distant. G‑d is infinite. Yes, He’s there in every mitzvah you do, every word of Torah you learn, every meaningful act of your life. But you can never get enough of Him. And so, there’s always closer and closer to come.

Make every moment of your day a moment of teshuvah. Never be satisfied with where you stand. It may have been the highest summit you could reach yesterday, but it’s the valley compared to where you can reach today.

Always be turning yourself around, spiraling upward.