Background: I grew up lower-middle-class. Had low paying jobs after High School. Always got along okay by being very frugal. Eventually went to college. Became an Engineer. Married a professional (No, not that kind of "professional"... a Nurse). Stayed a low-roller through all the years. I would collect gaming coupons and play them all and I would be disappointed if I didn't pay for the entire trip with the proceeds. Most times I was not disappointed. Now: I'm making a good salary and wife is making an even better salary. This last trip I decided that I would try to break from my low-roller ways and put some more money at risk. I was a complete failure. I had some good luck for the first two days but with only betting $5-$10 a shot at blackjack that only came out to about +$250. At this point I'm afraid to increase my bets for fear of wiping out my gains. I know I can afford to lose the gains and more but I simply hate the idea of losing money. Sadly, if I had been losing I would have done the same thing because I would be in fear of having a large loss at the end of the trip. Losing $300+ would be a large loss to me, psychologically, not financially. So... I really wish I could become comfortable with losing a bit of money so I can also see the potential of larger wins. Any ideas on how to do this?