I think that it's good that you've recognized this is an issue in your life. I tend to err on the side of TOO cautious, so it's hard for me to think of any ways for you to let your cautious side solve things. Maybe it would help when making decisions to seek out other people's reviews and advice on specific things. Like especially when it comes to colleges, there is usually a lot of things you can find online about the college, its reputation, and stuff about different programs and services you want or need.
"Whoever fights monsters should see to it that in the process he does not become a monster. And when you look long into the abyss, the abyss also looks into you."-Nietzsche
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