Everything happens for a reason?

Has anyone ever wanted to really do something but found themselves doubting their judgement? How about, have you ever really wanted to do something but had all types of obstacles and bullshyt get in your way- preventing you from doing what you want or feel you need to do? Well I have. I'm going through that shyt as I type! Sometimes it feels like no matter how much I throughly plan out shyt that I want to get done, there is always a bump in the road or obstacle I must get over. That itself results in me second guessing myself, plans, and actions. I am honestly afraid of failure and doing the wrong thing. I've made so many bad decisions in my life that I often find myself second guessing my decisions and judgement. So how can I resolve this issue that I have within myself? Being afraid and never taking risks seems like the fire proof way to go. But then I wouldn't be living my life, They say God has a plan for us and that if things are meant to be they'll happen. But I'm still wondering what my plan is. Should I just do my regular thing everyday and go to work, come home, hang out with some friends, and talk on the phone all the while hoping that one day, just one day something will just up and happen that will change my life on its own? OR should I MAKE shyt happen and take the risk of failing or losing out?