Over the past six months I've had a steady income. Overall, I'm down 6k, probably more, of my own money. The problem is, I'll win probably 50%+ of the time, but flush it all away. I'd say out of the 5k I've wagered I've easily won 15k. I remember a few months back taking $50 and for six hours before work I got it to an amazing $2200. AN HOUR before work I decided to gamble on a slot, $2000, little blackjack, $1500, slots, $1200, little blackjack $900. Not even realizing IT'S STILL $900 I go to a slot I always do pretty well at and decide to do $7 spins. I watch myself throw it down the drain.

When I'm winning it's great. If I begin to go too far down some alarms go off. It all becomes relative to the peak of what I had won, not what I have the moment; so that $300 balance that used to be $500, all on a $50 deposit, somehow is in the red. I'll do weird gambler math on why I should keep betting, or depositing. Other than losing because of that, it was losing because of using sites that don't let you cashout for quite some time.

I'm making assumptions, but I'll guess that some of this might apply to you. I actually gambled today, but I used a bitcoin site where I could take it out within an hour. I didn't go crazy (well, I always bet pretty high on things), and FOR ONCE, I listened to myself on my cutoff amount on my winnings.

Your OP isn't saying anything about an addiction or even constant gambling. I think it takes a certain person to flush that money down the drain. Some people will feel like shit after losing $50. It's disconnecting your mind from what that money could have bought, it's being in that moment and only thinking about the loses/winning it back. I think you need to do find ways to put the brakes on future betting because it's always harder once you actually have a constant stream of extra money.