“A man of crooked mind does not prosper”: “Crooked mind” is literally “crooked heart,” the same Hebrew expression used in 11.20 and translated by Revised Standard Version as “perverse mind.” See the comments there. “Does not prosper” is literally “does not find good” and is used in 16.20 without the use of “not.” See there for its sense.
“And one with a perverse tongue falls into calamity”: “A perverse tongue”, as in 10.31, refers to a liar, someone who does not speak the truth. “Calamity” refers to “trouble,” “misfortune,” or “distress.” To “fall into calamity” means to be ruined or to meet with disaster. For a model translation see Good News Translation. A rendering that displays more of the parallelism is: “A person whose heart is rotten will never succeed. A person who lies will surely find disaster.”
Quoted with permission from Reyburn, William D. and Fry, Euan McG. A Handbook on Proverbs. (UBS Helps for Translators). New York: UBS, 2000. For this and other handbooks for translators see here .

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