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I tend to ask myself questions every day, but I'm still learning how to answer them. The question I have been asking myself lately is if I'm on the right path to becoming who I want to be. I'm finding out the answer isn't as simple as yes or no. We don't know what obstacles we'll have to face to get there. Sometimes we have to work through those challenging days to make it to the other side. We can sometimes see an ugly day as a setback or getting off track of our path to where we're trying to get. However, all this can be a blessing in disguise.
I'm getting more and more okay with not knowing the answers to many of life's mysteries. Since life is full of questions, I think the point is to try to answer them through experience. Good or bad, the more experiences you have, the more knowledge you get about life. The more knowledgeable you are about life, the more likely you are to live the life you desire.
Whatever questions you're trying to answer right now about yourself/life, don't try to resolve them right away. There might be an experience that helps you answer it, good or bad.