As the questions says, when do you stop? your point of no return?
Usually, I'll stop when I've doubled my money, but sometimes it's the opposite.
As a player, I've definitely been in a position where it's hard to stop, and I'm pretty sure everyone has experienced the same thing.
For me, it's not a problem as long as we don't do it continuously, because it's not easy to always be consistent with what we have set.