The Sochotchover makes a guarantee: any Jew who has a true “teshukah,”a thirst and desire for G-d, will not end up in gehenom. That desire will carry them out of there.
The Shem m'Shmuel uses his father's yesod to answer Ramban's question on Rashi in our parsha. In Parshas Mishpatim, after the giving of the aseres hadibbros, Moshe was told by Hashem that he is going to send an angel to guide Bnei Yisrael (23:2). Moshe goes back up the mountain for forty days, and at the end of those forty days we have the events in our parsha, the making of the eigel and the destruction of the luchos.
Hashem again promises to send an angel (33:2), but this time, as Rashi explains the pasuk, Moshe objects, “Im ain panech holchim al ta’aleinu mi’zeh,” you, G-d, need to personally attend to us. If you are sending an angel, don’t bother, as that’s not good enough.
Ramban asks: how does Rashi’s reading here makes any sense? In Parshas Mishpatim, before Bnei Yisrael made the eigel, Moshe didn’t speak up or object when G-d promised to send an angel. Now, after Bnei Yisrael did wrong, after Moshe had to plead with G-d just to spare their lives, now he voices his objection to an angel and makes demands for more?! Moshe is certainly not in a good position to bargain here!
Maybe this is not a good mashal, but I'll try anyway. In many if not most jobs these days there is an annual performance review. I want you to imagine a guy who has been a slacker the whole year, who barely kept pace with his colleagues, who is the worst producer on the team.
The boss asks him, “So what are your performance goals for the upcoming year?”
“I want to become the CEO.”
The boss nearly falls out of his chair laughing, but then he sees that this guy is serious. The guy really no longer wants to be the slacker – he genuinely wants to make something of himself.
Who would you rather have on your team – the guy who racked up the best numbers last year, but is content to stay at that level and coast, or the guy who, even if he hasn’t done it in the past, is hungry to make something of himself now?
The difference, explains the Shem m'Shmuel, between the promise of an angel that Hashem made in Parshas Mishpatim and the promise he made now after cheit ha’eigel boils down to one pasuk: “Va’yishma ha’am es ha’davar ha’ra ha’zeh va’yisabalu.” (33:5) Klal Yisrael heard that Hashem was angry and would only be sending an angel and they mourned over the loss of the presence of the Shechina (Rashi). Klal Yisrael had been on the highest of high levels, they had just received the aseres hadibbros, but at that time they had no problem with being led by a malach. They were happy with where they were. Now, even though they were on the lowest of lows, having just done cheit ha’eigel, the news of the malach, the news of the loss of the Shechina, bothered them. They yearned to reconnect with G-d. It doesn’t matter where you are holding, even if it is in gehenom mamseh – what matters is where you want to be holding.