Machiavellian Problem in Politics

Central to Machiavelli's approach to politics is the idea of dissembling. How much of that dissembling becomes an invalidation of democracy itself? And is it useful to have a guilty conscience about dissembling so you don't do it too often or do it as little as possible? I come to the conclusion that it's good to have a sense of dirty hands, that you have to put on a mask and dissemble.