Knowing when to cut your losses on a trade depends on what your strategy is. If you're trying to top fish a stock with a short, then you would want to cut your losses if the stock were to break through its recent high—that's the point at which you know you didn't top fish at the right moment. Some traders may give more wiggle room with their stop-loss orders than others, but many trading strategies depend on either resistance or support holding. When it comes to cutting your losses as a day trader altogether, you may want to consider quitting if you are building debt or noticing negative impacts on your mental health.