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I can most definitely relate to what you are talking about, because this has happened to me more than enough times when am trying be very careful and be selective of the games I want to bet on probably due to the fact that I want to maybe use bigger funds than normal to actually bet on the selection and if there is anything like being too careful it's most definitely this particular feeling.
Such things are not entirely wrong and I think in some cases can save you from a big loss. When gambling has no extra consideration, then you may lose more than if you analyze more deeply. There are times when you need to lower your expectations of winning, there are times when you double your bet, it doesn't have to be the same all the time.
I also understand that when we think more than once about certain things, then in the end we will only be hesitant. In gambling I think this is good, it means you can control your greed rather than risking everything in one bet. It's lucky if you win, but if you lose, then you will definitely regret it very much.