Should You Miss Yeshiva After You Start Working?

This weeks episode sparked a debate. The conversation continues here.

Jul 10, 2025

This past week’s episode of Shtark Tank started a fascinating conversation, and I wanted to expand on it here. Our guest was Rav Reuven Berman, who was a mechanech before transitioning into the business world. One line that really stuck with me was:

“I still wish I could be in yeshiva full time.”

This was someone who had spent years immersed in Torah, planning to dedicate his life to learning and teaching. But life had other plans—or rather, other costs. By his 30s, he already had five kids and bills that didn’t match his paycheck from Chinuch in Israel. So he made a decision: pivot to a career in sales.

I asked him how he handled such a significant identity shift. His answer had a few layers, and some parts definitely raised eyebrows (including mine).

On a practical level, he found a few things to be crucial:

He didn’t get stuck in what could’ve been.
He made the most of every stage.
He found creative ways to feed his spiritual self—through teaching on the side, learning when possible, and connecting with the right chevra.

But even deeper than that, Rav Reuven introduced an idea he’s come to believe in over time—what he called two types of lechatchila. Here’s how he described it:

Working hard to support a family and raise children loyal to Hashem? That’s 100% lechatchila.
Sitting in yeshiva learning Torah all day? That’s lechatchila shebilechatchila—the best of the best.

In other words, this isn’t about compromise. It’s about reframing. A worldview that finds dignity and spiritual depth in both missions.

Can There Be Two Winners?

But here's the thing: is it really possible to have two types of lechatchila? Isn’t there usually just one gold medalist—one lifestyle that’s considered the ideal?

During the interview, I pushed back on this. Rav Reuven clarified: we’re not playing God. We strive to do what Hashem wants from us, and for many people, that means going to work to fulfill their halachic obligation to support a family.

Still, there’s something uniquely beautiful about the atmosphere of yeshiva. The energy devoted to learning. The slow davening where no one’s rushing out (even when the alternative minyan is full of people rushing to good, legitimate things). The presence of Talmidei Chachamim. He paraphrased Rav Aharon Kotler, calling this "peak Olam Hazeh."

This conversation struck a chord.

I think it's because this is one of the core tensions many Bnei Torah in the workforce struggle with. For those who thrived in yeshiva, it’s easy to view that period as the spiritual high point of their lives. But that leads to a painful conclusion: if that was the peak, then the rest of life feels like a slow decline. You used to be at your best, and now you’re just coasting—past your prime, washed up.

I’m glad Shtark Tank has become a platform for these conversations, and I wanted to use this space to share some of the thoughtful feedback this discussion generated.

A Message from God?

Rav Mickey Ellman messaged me after the episode with this perspective:

“I had a thought about how to define the difference between someone who’s working and someone who’s learning full-time. Obviously, both paths can be ideal—it depends on the individual. But here’s the core idea: if someone is sitting and learning all day but feels bored or is wasting time, that’s a sign he probably shouldn’t be learning full-time.”

He went on to say that if we look at life as an opportunity to resemble Hashem, then that resemblance can be expressed in different ways. For some, full-time learning is the clearest and most direct path. For others, they may fulfill that ideal more effectively through meaningful work.

Each person has to be honest about their own nature. For someone whose personality and strengths are better suited to the working world, forcing themselves to learn all day might not only be a waste—it might take them further from their true potential for resembling Hashem.

I appreciated this perspective and told Rav Ellman so. But I pointed out that it doesn’t fully address someone like Rav Reuven—a successful talmid and accomplished teacher who pivoted to business not out of boredom or underperformance, but because of financial necessity.

Rav Ellman responded that this brings us to the sugya of hashgacha pratis. Parnassah is one of the ways Hashem leads us to where He wants us to be. Even though it might look like someone is closing his gemara just for cash, that’s the wrong perspective. If financial needs force a lifestyle change, that might be Hashem’s way of guiding you to your next mission.

Torah Sources

Another thoughtful piece of feedback came from a LinkedIn comment by Yaakov Davis, which turned into a longer conversation via DM.

He raised a key issue: we don’t find the concept of lechatchila shebilechatchila anywhere in Chazal. Either something is lechatchila or it isn’t. From a textual point of view, he argued, we should be careful not to invent new terminology if it doesn’t exist in Torah sources.

He wrote:

“I do think this transition is hard for people because certain ideas have been drilled into their heads for so long. The evolution of those ideas is actually fairly recent. But I never see anyone quoting the actual Torah or sugyas that discuss this in depth. One day I hope people will get back to that.”

Yaakov continued:

“Echad hamarbeh v’echad hamamit, Hashem doesn’t desire quantity—He desires our attitude. And in His eyes, the two are equal. This is based directly on the gemara (Berachos 17). Rav Moshe in Derash Moshe even says that sometimes less can literally mean more! People like to put things in neat boxes, but that’s not how Hashem sees things. I just pointed it out because that kind of binary thinking damages how people see themselves and their spiritual potential.”

He also added a Torah source angle:

“If you look at the sugyos in Kiddushin and Bava Kama, according to the majority of Rishonim, ma’aseh—action—is greater than learning for oneself. Teaching others is the highest form, because it encompasses both.”

It’s interesting to note that even though we don’t find different halachic types of lechatchila, there are other similar concepts that are rooted in halacha. For examble, on chanuka, there is an obligation to light one candle, and there is also the mehadrin route of lighting many more candles. So we see that there can be levels that are all considered a mitzvah.

Rav Reuven Responds

I circled back with Rav Reuven Berman to get his take on these comments. Here’s what he wrote:

“In reflecting on the beauty of Yeshiva, I've also thought (as I had alluded to in the podcast with comments about the minyanim) that sometimes people fall into downplaying the other to make themselves feel better about their situation. You shouldn't downgrade the yeshiva life or kollel life in order to make yourself feel better about your place in the working world.”

He had a similar response to the point about the sources that Yaakov David quoted

“As I said above, I completely agreed with this. But we need to make sure we are building up and not downgrading. It is also true that a תלמיד חכם gets שלישי and certain כבוד and the like so we have to give that pursuit the כבוד it deserves. Even if in שמים the שכר will be the same, in עולם הזה we are supposed to relate to things differently.”

What Do You Think?

I would love to keep this conversation going. Does this resonate with your experience? And how do you define your own lechatchila? Looking forward to seeing your comments!