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It's not luck with meaning but luck that you gave meaning to isn't it? I mean if the same process was repeated but you instead gambled it more it probably wouldn't be called serendipity anymore because, well, you didn't do jack with the money to help you. So it's just luck with extra steps. At least from what I undestand anyway.
Personally it was just one time, the time when I won the biggest I had so I was able to go to a trip with my family outside the country. I didn't get a lot though so a lot of the other expenses were still shouldered by me but the win definitely helped jumpstarting us to actually being able to go on that small vacation. Still enjoy the memories I had of it really.
We all know that gambling depends on luck. So we cannot win again and again. If we win big once, we should definitely enjoy that win.
I really like the way you used your gambling winnings. You went on a trip with your whole family. We should also enjoy the money we win in gambling in a way that becomes a beautiful memory in our lives.