My problem with understanding the opposite

Initially, what I was interested to learn about is about democracy. Ended up I learn something additional which incidentally very useful to me, especially when doing my job here. In the carrier that I pursuing right now expose my vulnerable "me" to the outside world, which I can say a messy world that operate in orderly structured system. It is either I become a victim of the society or I have capability to impose control over it. I always keep on struggling to find the answer why I can't cope myself into the corporation as others did, and I all I get is self-destructive replies which like "don't try change things that is out of your locus of control!, look into stoicsm and keep on living!". It really true that Stoicsm, had reveal some of the painful truth to me, and all I need is to digest all of the information and have different perspective in life. Ya, I'm very lucky that I'm being born in a loving ordinary family, where need not face any hardships as others did. Stories reminded me that I much fortune that I have right now and I have no reason to complaint. Still, I feel something is not done, something within me remain incomplete here. What is that? 

The more I learn about theory in philosophy, the more my thought become so messy. I learn about existentialism, nihilism, and freedom. Maybe all I can't see in the theory dept like what philosophers did, which makes me doubt more. People can always challenge my thought, which I fear the most. Maybe people did not challenge my thought, it is me myself that did so. I don't like the feeling of uncertainty, no matter whether it is related to my working life or my personal life. Uncertainty kills my confidence, stopping my progress. At the same time, uncertainty keeps my curiosity going. Haiz. Damn it. 

Maybe it is more rational to leave everything vague behind and treat all I have learned as an entertainment. Ya, why give a fuck on those meaning of life at first place as you are not one who choose to born into this place?(my mother will definitely feel very sad if she heard that.) No matter what the world trying to tell me about what I'm going do with my life, I should just let it be. Somehow I saw a quote from my colleague:" Have faith and go with the flow". Go with the flow, and don't question too much.