I think you're right, and there's definitely a balance to be had here. The first time I came across the notion that there might be a downside to keeping everyt

I think you're right, and there's definitely a balance to be had here. The first time I came across the notion that there might be a downside to keeping everything 'hypothetical' was in reading William James (I think it was in his Pragmatism lectures). He points out the opposition between 'thought' and 'action'. There is a tradeoff in continuing to think about certain subjects in that your ability to act on things related to the subject is impaired. If there is nothing left to question in relation to some domain in which you'd like to act, then the actions you take will carry force and generally be more effective. A more concrete example: let's say you're a tennis player and working on improving yourself. You can keep on questioning whether a certain technique for swinging is the best one or not, and if you keep questioning for a longer time, you have a better chance of finding the best technique. But, you're ability to execute that technique is another thing entirely, and if you're still questioning it while playing a game, you will perform worse than if you acted with conviction. In life, perhaps unfortunately, we don't get the clear distinction between when it's a 'game' vs. 'practice', and force of habit is a thing, so how to handle this for optimal results is not such an easy problem.