KDL,
I understand what you're talking about and yes...isn't it the ultimate Catch-22? You've committed to only making clear and rational decisions, but have been living in addiction so long that you have no way of knowing what constitutes a clear and rational decision. And it seems that you're like me in that you want a simple and practical way to figure it out.
I can't tell you a perfect answer to this, but I can tell you what I did. First, I started talking to other people, friends, family, and most importantly a licensed mental health professional, about the decisions I was facing. I quickly learned, from trial and error, whom I could trust to help me make good choices, and I started sticking my toe in the water of life and making some decisions. Small ones at first, like starting to ride a bike with training wheels. After a while, I got comfortable with making bigger and bigger decisions, and finally I got to the point where, most of the time, I am confident that I know how to make good choices. I still ask for help and for the opinions of others when I need them, though. None of us is perfect and has all the answers all the time. It's never a bad thing to get a reality check from a trusted person.
I believe it's important though, when "trying on" new behaviors after quitting an addiction, to be gentle with ourselves. It sounds to me like you have perhaps walled yourself off a little bit from life, in fear of making imperfect decisions. That's being really harsh with yourself, IMHO. Perhaps you'd be more comfortable if you took it slowly and made a few decisions, giving yourself permission to be wrong sometimes.