taking risk

When will I become skilled at taking risk? last day when our SAD group had a quick chitchat (open forum) with our SAD professor about our proposed system and as expected, he keep on asking us that “is it worthy?” Last time, we are asked if the system we proposed are ‘kindda’ worthy of our four years learning at the university. If I will be asked, I would really say “yes” (for some reasons) but on the other side it’s not really worthy. I am a USEP student. I am known to be one of the intellectual giants in the institute of computing. But why is it hard for me to please my self that I can do better than what they think of me?
Upon dealing with challenging proposal, I never really open my mind perhaps because I am not ready to accept failures. I can always think of better ideas, far more challenging than we are proposing now. But I can never deny the fact that when time comes that we will be in the point of implementation, we can’t finish it completely ---- far more than an intellectual giant do.

What am I supposed to do? I need to take a night to reflect. How sad. As far as I know as regards with what I am, I will really need lots of whole night for me to think and reflect before I can realized what am I doing and what I need to be doing.
Not taking risk affects me self-confidence, self-worth, what I do and what I do not do in life. Maybe I am so stupid not to trust my own intuition, capacity and thoughts.

I am struck, not just once but twice. Do I need to hear another one before I will be able to realize what I need to realized? Its time to wake up now and I now I can always do better. Maybe it is just a matter of self-possession and a lot more trust in what we can do.

But HOW? Or maybe the right word is WHEN?