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The Mashgiach in one of the yeshivos I went too (can’t say which but it’s a biggie) once told me that he is actually two Mashgichim – the ‘PR’ Mashgiach and the personal Mashgiach. The ‘PR’ Mashgiach gets up and gives shmusen on staying in learning, the personal one tells individual bochurim, in private, what he thinks they should be doing. He told me that I would be surprised at how many bochurim he’s told to go to university and even more surprised at who these bochurim were. Having said all that, he did once give a series of shmussen on business ethics and chemdas hamomon which he prefaces with a statement along the lines of “whilst many boys here will be surprised at me giving these shmussen the truth is that maybe 5 or 10 bochurim in this room are ra’ui for staying in learning long term. Everyone else needs to know how to do work when they get there.” Those weren’t his exact words, I know (it’s coming on for 6 years since I heard the smooze…) but it’s a pretty fair representation of them…