I definately can relate to what you are saying. I find it difficult to tell people that I am in need so I get what I need on my own. to some people I seem like an independant person but really I'm too scared to ask for help. I feel guilty or I feel like I am annoying the person by asking for too much. For example: I wanted to have higher grades in highschool, I wasn't able to ask my teacher for help because h was very intimidating, so I got his attention by riting him an email about how he hurts my feelings, and then finally he was able to get down to why I had really written the email. It was because I admired him and wanted him to help me in his class.
All I can advise is that in the workplace you make aquaitances wih staff members so it's not too hard to ask them things
at school make friends you trust so it is easy to askthem for help.
just be confident in yourself
It's kinda hard to describe what to do but I hope this helps or at least makes you feel better
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"...I still haven't found what I'm looking for..." (U2) 
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