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Dear Eric
As I see it, it is not your decisions that are the problem. Until you have dealt with the anxiety and overthinking that appears to run your life, the peace, contentment & happiness that you are constantly chasing after will always elude you.
Staying grounded in the moment instead of second guessing past decisions and worrying about hundreds of different possibilities of the future especially the negative ones. The practice of mindfulness ,tai chi, yoga etc are designed to bring you back to the present and allow your mind to rest from the torment of being dragged into the past and future. The zen story on you tube good bad who knows?, may also help.