Avi Steinberg thinks Philip Roth gave Talmudic Advice to Julian Tepper

In New Yorker we learn that Avi Steinberg ("IS WRITING TORTURE?") thinks Philip Roth gave Talmudic Advice to Julian Tepper.

Steinberg describes a literary storm between Elizabeth Gilbert and Roth wherein Gilbert defends writing as a happy profession, contrary to Roth who allegedly did the following to Tepper:
Julian Tepper published a piece describing an encounter with Roth at an Upper West Side deli. Waiting on his hero’s table, Tepper tremulously presented Roth with “Balls,” his first novel. Roth warmly congratulated him, and then offered: “I would quit while you’re ahead. Really. It’s an awful field. Just torture. Awful. You write and you write, and you have to throw almost all of it away because it’s not any good. I would say just stop now. You don’t want to do this to yourself. That’s my advice to you.”
Steinberg thinks he knows that Roth really loves writing but was pushing away the young writer to test his dedication. This reminded Steinberg of the Talmud.
...[Roth's] newest message, we are told, is: “Don’t write. Get out while you can.” But what did he really mean by it? My guess is that he was joking. Which isn’t to say that he wasn’t serious. It was a serious joke. Roth’s cranky advice for the young writer is an old Jewish chestnut. The sages of the Talmud offered the same piece of advice to anyone who wanted to join the faith: don’t do it, it’s seriously not worth it, it’s just an objectively bad idea. The ancient rabbis suggest that you ask a potential convert, “Are you not aware that today the people of Israel are wretched, driven about, exiled and in constant suffering?” It’s a rhetorical question. But if the person replies that he or she indeed embraces wretchedness and constant suffering, you explain to him or her how taxing it is to practice the religion. You mention the gruesome punishments for breaking the Sabbath and other laws. You try very hard to dissuade any would-be applicants. You mess with them—and that is how you welcome them. Joining, in other words, happens through a process of opposition, irony, and dissent. If you’re going to join a messed-up club, you have to pass the messed-up entrance exam. You enter into the sect only when you push back, when you finally say, Listen, I don’t care what you tell me. I know it’s a bad idea, but I’m determined to do it, and I will do it.

That’s the kind of a person it takes to be a writer: someone who’s zealous and ready to argue, someone who has Philip Roth tell him, “It’s torture, don’t do it,” and replies, “You had me at ‘torture.’ ” You don’t enter into it because it’s a great lifestyle decision—it isn’t—you do it because, for whatever reason, you believe in it, and you believe in it because, for whatever reason, you need to believe in it. Roth was messing with Tepper; he was testing his faith and strengthening it. He wanted the guy to earn the title: author of the novel “Balls.”

My guess is that Tepper was heartened to discover that even the great Roth, it turns out, hates his life. For struggling writers, wretches that they are, that is inspiring.
If Steinberg is right then Gilbert was wrong about Roth when she, "launched an earnest defense of the scribbling life, declaring that writing is a “fucking great” job. This is a classified piece of information, she claims, kept secret by vain, jealous older writers."

Turning the question back on the rabbis, is it true that the conversion to Judaism must always be preceded by a Rothian "messed-up entrance exam"? If the answer to that question is always yes, we are sad. Surely there must be some rabbis who (like Gilbert does for writing) are willing to tell people that Judaism is a “fucking great” religion.

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