One of the big questions you have to ask yourself when you play blackjack is when you are going to leave the blackjack table. This is as getting down is a lot easier than getting up. But unless you are playing free blackjack losing money is an issue and even if your Blackjack strategy has been paying off and you’ve won money - when do you stop and call it a night.
Only you know the question to that. If you are playing well and on a hot streak why would you stop? Then again you never know when the streak is going to end. It would be poor Blackjack strategy to turn a night where you are up $15,000 finish up to a night where you made $2,000. And even though you made money you won’t be able to stop feeling like you threw away $13,000 at the blackjack table. When you are playing Blackjack for free none of this matters but the fact that real money is on the line is what gives the game the edge.
Regarding of whether you are winning or losing, one of the first things you should appreciate when you learn how to play blackjack is that you need to keep your emotions in check. Don’t try to get back what you’ve lost all in one go. Stop and take a break. Blackjack is a cruel game and knows no emotion so at the blackjack table you can’t afford emotions either.