Should I give up? Judaism gave me an interesting answer.

I thought the question was whether to hold on or walk away. Judaism taught me the deeper question is whether I am willing to evolve before I try again.

photo: Salvatore Favata/Unsplash

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This is a guest essay by Vanessa Berg, who writes about Judaism and Israel.

You can also listen to the podcast version of this essay on Apple Podcasts, YouTube Music, YouTube, and Spotify.

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I have to admit, I am struggling with something: when to let go and move on, and when to keep on keeping on.

When is persistence a virtue, and when is it just stubbornness dressed up as courage? How do I know whether another attempt is an act of faith, or simply a refusal to accept what reality is trying to tell me?

I wanted to know how Judaism would guide me through this psychological and emotional maze — because I don’t think “keep on keeping on” means doing the same thing over and over again and expecting different results.

Indeed, parts of Judaism advocate for moving on. Kohelet (Ecclesiastes) tells us: There is “a time for embracing and a time for shunning embraces … a time for seeking and a time for losing … a time for keeping and a time for discarding.” Apparently there are things we are supposed to fight for. And there are things we are supposed to release.

But Judaism is not a culture or philosophy of giving up, at least not easily. Our patriarch Jacob spends an entire night wrestling with a mysterious being. Dawn comes. Jacob is injured. His hip has been wrenched from its socket. The being tells him to let go. Jacob refuses, saying: “I will not let you go unless you bless me.”

And then something remarkable happens: Jacob receives a new name, Israel (Yisrael), because, he is told, he has “striven with beings divine and human” and prevailed.

Think about what that means. Thousands of years later, the name we still call ourselves (Am Yisrael — the People of Israel) and the name of our country were born in a wrestling match. We are not named for serenity or acceptance. We are named for struggle.

And there is another part of the story that matters just as much. Jacob does not walk away from that struggle unchanged. He walks away limping. He walks away with a new name. The man who entered the fight is not exactly the man who emerges from it. That, to me, may be the Jewish definition of perseverance: Hold on, but allow the struggle to change you.

There is also a stupid kind of persistence. I know it because I am capable of it. Try something. It doesn’t work. Try it again. It still doesn’t work. Push harder. Explain better. Give more. Want it more. Then become frustrated that reality has somehow failed to respond to the sheer intensity of my efforts.

But maybe the problem isn’t that I haven’t fought hard enough. Maybe I haven’t fought intelligently enough.

There is an incredible teaching in Pirkei Avot (Ethics of the Fathers) from Ben Bag-Bag, a rabbinic sage and disciple of Hillel the Elder. He said: “Turn it over, and [again] turn it over, for all is therein.” He didn’t say stare at it harder. He said turn it over. Look again. Change the angle. Interrogate assumptions. See something you couldn’t see from where you were standing before. And then turn it over again.

That is entirely different from doing the same thing repeatedly. In fact, one medieval commentary on this teaching explains that if you do not find what you seek the first time, you may find it on the second or third examination — because each return can reveal something the earlier one did not.

There is persistence in that, but there is also humility. To turn something over means accepting the possibility that my first interpretation was incomplete. My first strategy may have been misguided. My first instinct may have been off. I may have been wrong.

And yet Judaism doesn’t therefore say: Walk away. It says: Turn it over again.

Rabbi Akiva’s life offers another version of the same idea. He was 40 years old and had never studied Torah. One day, standing near a well, he noticed that dripping water had carved into stone. If something as soft as water could penetrate something as hard as rock, he reasoned, perhaps Torah could penetrate him too.

So he began learning — at 40 years old, from the beginning. He sat down with children and learned the alphabet. The man who would become Rabbi Akiva, one of the greatest sages in Jewish history, first had to accept being a beginner. That is persistence too. Not merely working harder, but being willing to start differently, being willing to look stupid, being willing to admit what you don’t know, being willing to trade ego for progress, and then continuing long enough for water to reshape stone.

Judaism seems deeply suspicious of the idea that failure means something should automatically be abandoned. Proverbs tells us a righteous person falls seven times and rises again. Rabbi Yitzhak Hutner made a beautiful observation about this notion. We often imagine that a righteous person becomes great despite falling repeatedly. Hutner suggests something more radical: The rising comes through the falling. The failures themselves become part of the person’s eventual greatness.

In other words, falling is not necessarily evidence that you are on the wrong road. Sometimes falling is how you learn to walk the road.

If I fall seven times in exactly the same hole, for exactly the same reason, and learn nothing each time, I am not sure Judaism would call that perseverance. But if every fall teaches me something — about myself, about another person, about fear, self-control, about discipline, about communication, about patience, about what I thought I knew but didn’t — then attempt number eight is not really attempt number eight. It is the first attempt being made by the person who survived and learned from the previous seven. That is a very different thing.

And perhaps no Jewish idea captures this better than teshuvah. We usually translate teshuvah as repentance, but the word literally means return. The Rambam says that complete teshuvah occurs when a person encounters essentially the same situation in which he previously failed, still possesses the ability to make the same choice, and chooses differently. Same situation, different response.

That may be one of Judaism’s most important insights into human change. The goal isn’t necessarily to make sure I never encounter the struggle again. The goal is that when I encounter it again, I am no longer exactly the same person. That requires reflection, taking responsibility, and asking painful questions.

What did I do wrong? What was I afraid of? Where was my ego involved? What did I misunderstand? What skill did I lack? What would I have to adjust or change before trying again?

There is another extraordinary passage in the Talmud that goes even further. King Hezekiah is sick. The prophet Isaiah tells him that a decree has already been issued against him. In other words: It’s over. Hezekiah refuses to accept that conclusion. He tells Isaiah that he has received a tradition from his ancestors: Even when “a sharp sword rests upon a person’s neck,” one should not stop seeking mercy.

Rabbi Yohanan and Rabbi Eliezer repeat the same teaching. Even when the evidence looks terrible, even when you think the outcome is already decided, don’t surrender hope prematurely.

That does something to me — because Judaism seems to warn us about declaring things impossible too quickly. There is reality, and then there is our interpretation of reality. Those aren’t always the same thing.

A setback is real; that does not necessarily mean the goal is impossible. A failure is real; that does not necessarily mean another attempt will fail. Something being extraordinarily difficult is real; that does not necessarily mean it isn’t worth fighting for.

Rabbi Tarfon puts the obligation beautifully: “It is not your responsibility to finish the work, but neither are you free to desist from it.”

I used to focus on the first half: You cannot control the outcome. True. But look at the second half: Neither are you free to desist. I don’t control whether I ultimately get everything I am fighting for. I do control whether I continue doing the work.

Maybe that is the answer I was looking for: Keep fighting. And after every failure, learn. Turn it over. Question yourself. Change the strategy. Acquire the skill I didn’t have. Develop the patience I lacked. Control the impulse that led to self-sabotage. Listen to what the last failure was trying to teach me. Become someone capable of succeeding where the previous version of me could not. Then return.

And if I fall? Rise. And if I fall again? Rise, differently.

Jacob refused to let go; he became Israel. Akiva refused to believe 40 was too late; he became Rabbi Akiva. The righteous person falls seven times; they keep rising. The Rambam’s penitent returns to the same place, but makes a different choice. Ben Bag-Bag advises us to turn it over and turn it over again. Hezekiah tells us that even with the sword at our neck, we are not entitled to despair.

Judaism’s message about when to let go and when move on isn’t so complicated after all.

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