Anyone who gambles with a feeling of "I am going to regret this" might not have a good time even if they win. It is too much stress.
You should
gamble if only you are in an unstressed mindset. This is why some people prefer to drink alcoholic drinks, although too much and the next morning will be a feeling of regret again

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That just means he can’t really afford to lose what he’s staking. With that kind of mentality, even if you win at the start, you’ll still end up losing in the long run. You only will not feel confident about the money you risk, and deep inside you’re always thinking it might be gone. So instead of having fun, you’re just playing with fear. I think the better mindset is to accept early on that losing is always a possibility, even if we’re aiming to win. That way, it won’t hurt as much when it happens.