I'm not exactly sure of the point of your post, but you seem to be confused, so I thought I would reply with some of my observations.
Firstly, introversion and shyness aren't necessarily related. Introversion just means more interest in the internal world than the external world. This will be seen as shyness. Basically, introversion is when the person doesn't want to act. Shyness is when the person wants to act, but he/she doesn't (usually because of lack of confidence, anxiety, or internal conflicts). It seems to me you're confused if you want to move past introversion and be a bit more extraverted, but not sure if overcoming the shyness is worth it. Maybe you already see all this, but it's important to be definite.
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Originally Posted by Gilda
This does have an upside to it. It keeps me from saying or doing things that are stupid, foolish, offensive, and thus being embarrassed.
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I hope that you understand that this isn't necessarily an upside. It's only an upside due to your insecurity. If you were more sure of yourself you wouldn't care so much about what people think of you, and doing something stupid wouldn't affect you so much. Everyone does stupid things sometimes. I'm sure you know plenty of people who do stupid things all the time and don't let it get to them.
Think about what is happening: you want to do something, but fear what *other people* think of you if you do it. You are letting *them* choose what you do, giving them the power. Is this what you want? Or would you rather do what you want to do?
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Originally Posted by Gilda
And I think that most of the time, that's how it works. There's a downside, in that I tend not to have many friends, countered by an upside, which is that I don't tend to offend people and thus make enemies.
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Again, it's a downside because of internal reasons. If you change yourself (become stronger) then the downside is gone, and only the upside is there. I really hope that you understand that, since I think you'll be much clearer on what you want to do if you see that. Negative stuff happening is no big deal -- it's only if you let it affect you, that's bad. Other people are less shy because they don't let those things affect them, and therefore they are less fearful of them.
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Originally Posted by Gilda
Sissy doesn't understand how I can wrangle 25 12-year-olds or give a presentation to 200 colleagues, yet be afraid of telling the waitress I haven't been served yet. It seems obvious to me. In those situations, I'm the authority figure; it's my turf so to speak. I'm granted an automatic measure of respect as a result of my position. The same isn't true of a restaurant, or store, or any other public place. I have no power, no authority granted there to build on save whatever the particular people working there choose to grant me. There's no way to transfer from my professiion to personal life.
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Yes, it seems obvious to me too. You are letting other people decide the power. You act with confidence when you know other people will perceive you as confident; you act with shyness when you feel other people might perceive you as a dork (or whatever).
You keep talking as if being less shy will cause negative things to happen to you, but the things aren't negative in themselves; they are only bad if you let them get to you. You can choose to be embarrassed or not if the restaurant doesn't want you. Well, maybe not, but you can work up to it as you gain self-confidence.
You are a different person, but the differences you are referring to in your post are restricting differences that you will be happier without (too easily influenced by other people's opinions of you).
If you aren't sure you want to be less shy then don't try to be. You can't become more assertive without the motivation to change and right now you don't, so don't bother. I suggest work on your self-confidence: when this builds up, you will be less fearful of confrontation/embarrassment etc. and overcoming shyness will be much more attractive. Then you can use that motivation to do that. Build your self-confidence by learning more about yourself, and becoming confidence on who you are (and who you aren't). When you are confidence about who you are, you will be less concerned if people disagree with those conclusions. (Example: If you are confident that you are an acceptable person worthy of eating in that restaurant, you won't be hurt by people thinking you aren't; you'll just see that it says something about them, not you.)