but when is the best time to stop gambling and take a break?
1-when you lose?
2- when you win?
It will be foolish to take a break from gambling when you win, the only issue here is when the gambler continues to gamble due to overconfidence and greed, then it's time to take a break. But there is no problem if he has a plan and sticks to it, winning should never be the barrier. However, such a gambler is not taking the break because of the "win" but for the emotion that has taken hold of him.
As for losing, it's better you also take a break if you are becoming increasingly desperate to gamble, especially if it has turned into a revenge quest that has led to addiction.
there's nothing wrong if you choose to take a break from gambling after hitting a certain win. There are a lot of people that want to hit a big jackpot and exit gambling or go off gambling for a while. If after winning you still continue gambling at that pace, their is an high probability that you might likely loose most of the money back to gambling if care isn't taken which is the reason why some feel when you've won you should take some break away from gambling. For me, the amount you've won determines if it's necessary to take a break from gambling or you should continue gambling. If it's the regular amount you've been wining in most of your games, then it's not reasonable to quit when you're on the winning side but if you've hit a jackpot, it's totally not wrong to slow down at such point. So as not to find yourself in this mix where you aren't sure of what to do at these different circumstances, it's best to have a routine you're to stick with so even after you've won a jackpot to get tempted to still continue gambling, you're certain you're never going above your range.
Gambling isn't about money, it's about control. Winning big? That's not a prize; it's a test. Your discipline is on the line. You have to reason carefully. You are indeed at disadvantage from the odds. A lucky streak shouldn't cause you blindness. Hit the jackpot? Step back. Re-evaluate. It's about your whole damned life, not only about the next bet. It's about equilibrium. The excitement of victory against the discipline to turn away. You need a schedule, a structure. Let not the game rule you. You rule it
Discipline. Routine. Reflection. That's how you change the game