Are you going to heaven/equivalent?

It seems like there are a lot of passages in the Bible that say it is tough to get to heaven, yet I keep hearing people say they are saved and definitely going. Is that an evangelical thing or a Christian or religious thing more generally? If you have that certainty, is it OK to use it to pass judgment on others or is charity still the #1 virtue? I sometimes wonder if religious figures would come back and pat their followers on the back or if they'd come in here and upend the metaphorical tables and tell people they were missing the point.

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