Hard but Sure vs. Easier yet Questioning

When you have a problem in life I've noticed there are two main types of things that happen. Now when I say problem, I don't mean what to wear to school. I'm talking about a problem that will affect you fairly strongly. One situation is knowing what is right, but knowing it is a hard task. The other is having options that may not be as difficult in the first situation, but it is not clear which option will make things better for you.
In the "easy yet questioning" situation, I find things harder to deal with. If you don't pick the right course of action you might end up losing something or someone you really care for. Situations like this create the weekends where I wake up thinking about it, sit around all day talking to people about it, and go to bed still thinking about it. I always think about it for as long as possible and go back and forth about 13 trillion times before my decision is made in the moment it has to be made based off where I am at that moment. While it may not be hard to do whatever the decision is, the decision could mean failure and hurt. I am the type of person who cares a lot about each thing and especially each individual person in my life. This leads me to analyze these situations for so long that it drains me and no matter what happens, the situation will have hurt me.
The "hard but sure" situation is the one that I would almost always rather have. I like having the directions laid out for me, even if they are difficult ones to follow. Yes these situations make me think and talk to friends about it too, but in the end I know what I must do is for the better. I've had friends come to me saying, I know that I can't talk to him right now, that waiting like he said will make things alright, but I just can't do it. I tell them to fight. That's mostly what these things take, is fight. That's something I have pumping through my veins and something that lives in my heart. I'm the kid who plays until the clock says 0:00 no matter what the score. That's why the situations are easier for me. I do believe that everyone can through any hard time, it just may require more outside motivation for some. At least in this you have a sense of what will make things right.
Some problems in life are just not easy. It's plain and simple. But for me at least, I would rather have directions that require a lot of fight than to leave it up to lengthy thinking about what could possibly help.