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Is it normal to always think way too deep and depress yourself in the process? I always see the downside even when I recently won the lottery it caused me to then question if my new found riches would make me unhappy.
That's called being pessimistic. It's not an insult. Just means you see the glass half empty instead of half full. But changing your perspective is easier than you think. You just have to remind yourself that nothing is ever as bad as it seems and think about what's good in your life instead of what's bad about your life.
Some people are just like that and it gives me the shits, because it's possible to change your perspective.
A former lover of mine recently inherited a very valuable house after her mother died: she already owns one house and two cars and all she can do is whinge about the selling agents having put up the wrong signs and that she has to empty the house before settlement in 4 months time, but won't accept any help to do it.
I'd be happy just to have a secure roof over my head I didn't have to pay rent for, then I wouldn't have to do the stupid job I do to support myself.