Toddlers and Lighting Technicians

I'm applying for jobs, because there's now only five months until my current one ends and it took much longer than that to get this position. It's annoying, because the time elapsed between applying to work for the British Council and starting the work far, far outstretches the amount of time I will be working for them. I'd kind of like to be paid in retrospect.
That's not going to happen.
Anyway, job applications mean not only updating the old Curriculum Vitae but also writing personal statements, cover letters and just general boilerplate. I actually have to admit a slight passion for writing about myself (imagine that); especially when I get to make it sound like my own Wikipedia article. Case in point:

I am an active dramatist, humorist, journalist and poet.

I actually wrote that in an application yesterday. I guess what I enjoy about writing such things is the opportunity it affords me to pomp myself up: in certain circumstances in social interactions, we are allowed to admit to a particular strength or flourish that we believe we possess. However, more than one at a time and what was once confidence begins to feel like boasting or, worse, arrogance. I'm not saying I want a society where everyone is suddenly allowed to go around declaring themself God's gift or even just a particularly adept human being- I've spent too much time around toddlers and lighting technicians to know how irritating that gets- but I do wish that my parents hadn't instilled in me such a disdain for pomp. I wish I knew how to take a compliment, which is not something I was ever taught, despite doubtless being praised far too much as a child. See? I don't feel like I can even write about this subject without throwing in a healthy dose of self-deprecation just to show that I'm not arrogant.
I think arrogance and dullness were the two things I was raised to be most vigilant for: I remember very clearly my mother telling me I was being boring and to stop talking if no one wanted to listen to what I had to say. And I can recall word for word Mrs. Sharpe berating me for boasting. The thing is, I know that a lot of contemporary acquaintances will be rolling their eyes as they read this, and muttering how I've never seemed too bothered about being tedious or concieted, and I feel I have to acknowledge this because otherwise I'm not admitting the flaws that I have.
I feel I'd be a lot happier if I didn't care about such things. Certainly, I'd be less self-conscious and that could only be a good thing (yet again, I feel compelled to acknowledge the folks who would say I've never been conscious of anything in my life and to simultaneously acknowledge that constantly acknowledging these things is boring for you to read). I spend almost all my social interactions, except those with the people around whom I'm absolutely, completely comfortable wondering if I'm holding up my end of the conversation, if I'm coming across as too self-interested or banal and if the other person has picked up on the fact that only half my brain is dedicated to this conversation because the other half is desperately monitoring my even action.
I don't know why I'm writing about this, other than writing my personal statement made me pensive and I haven't updated this thing in a while. I don't believe there's an answer to this, other than alcohol- although that doesn't really silence my self-conscious side so much as take its hands away from the reins of my body and mouth. I also now feel that I must mention that I don't dare think I'm unique in this situation: although, like a lot of middle-class children, I was always told that I was special, I was somehow also simultaneously discouraged from believing this.
How does that even work?