I don’t believe one can plan too much. When I say that, I’m saying that it is always possible to be more thorough in your approach.
However, it is possible to be too obsessive in your approach.
There is a distinct difference: Being obsessive means that doing what you’re doing degrades the long-term quality of your life.
Sure, it would be great to consider every single factor; to count every calorie, to account for every dollar going through your business, to know how you’re going to optimise every minute of your time, etc. In fact, if you manage to do that, your objective results may be better.
But life isn’t objective. Therefore, we should try to be as thorough as possible, and push for the finer details insofar as we can handle the consequences. The real question here is, “Do you know what the consequences are?”
Once you’ve answered that, you’d likely have found the line between dedication and obsession.
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