There is nothing more imprudent than excessive prudence.
— Charles Caleb Colton

The only guide to man is his conscience; the only shield to his memory is the rectitude and sincerity of his actions. It is very imprudent to walk through life without this shield, because we are so often mocked by the failure of our hopes and the upsetting of our calculations; but with this shield, however the fates may play, we march always in the ranks of honor.
Winston Churchill imprudent quote

We, perhaps, have corrupted our children and our grandchildren by heedless affluence, by a lack of manliness, by giving the younger generation more money and liberty than their youth can handle, by indoctrinating them with sinister ideologies and false values, by permitting them, as young children, to indulge themselves in imprudence to superiors and defiance of duly constituted authority, by lack of prudent, swift punishment when the transgressed, by coddling and pampering them when they were children and protecting them from a very dangerous world
— Taylor Caldwell

So long as the law considers all these human beings, with beating hearts and living affections, only as so many things belonging to the master -- so long as the failure, or misfortune, or imprudence, or death of the kindest owner, may cause them any day to exchange a life of kind protection and indulgence for one of hopeless misery and toil -- so long it is impossible to make anything beautiful or desirable in the best-regulated administration of slavery.
— Harriet Beecher Stowe

Every one goes astray, but the least imprudent are they who repent the soonest.
— imprudent quotation by Voltaire