Hey Adam!
Knowing that you’re an Enneagram 5/6, as well as an ISTJ/ESTJ, it makes a LOT of sense why you struggle with over-analyzing your choices. Those personality types are particularly known for that! And I’m guessing, because most of us experienced this, that you were likely rewarded for being logical and analytical throughout your life; which then makes it harder to break free and use our other discernment abilities (like emotions and intuition). And it’s really those latter two things that we need to build up if we’re going to make decisions that actually FEEL good, not just sound good or look good on paper. Excited to help you do that! 🙂