I have become self conscious and it scares me

When you said "Now I have this feeling that people are wondering what this round bellied middle aged man is doing taking a photo of that...." it says to me that this isn't a photography issue. It's a general life issue that's effecting your photography. In other words, it sounds to me like you're lacking in self esteem. So I would start by addressing that. Maybe start an exercise program. Those are great for your self esteem on so many levels. They help you to control your appetite, which combined with the exercise, improves your physical fitness and helps you to lose weight. That improves your body image and gives you more energy. Feeling physically tired can make you mentally tired which can make you depressed. Exercise also helps to regulate your hormones, like testosterone, which can fight depression on a chemical level. Falling testosterone levels as you age usually have a negative effect on your self esteem.

In the short term, buy a photographer's vest. It should change your image of yourself and make you less self conscious. With a photographer's vest on, you'll look more like a photographer hard at work than a "round bellied middle aged man" with a camera, creeping around.

Yes, this has always been an issue on the street. I adapted a shooting style for humans in the street that includes not putting camera to my eye until I'm ready to snap. That means everything is set before and I'm waiting for the right moment...however, standing still on the street corner is also problematic...so I tend to watch the street around me while walking around, spot a scene, set camera, and proceed to walk through the scene pausing briefly to compose, snap, smile like a fool, and keep walking...I think Winogrand did something similar... I avoid that which looks dangerous (young punks with guns, Hasidic men in packs of 4 or more) I find waist level finder point and shoot, any old folder avoids suspicion. When I have been confronted I gauge my response based on their level of anger. For angry people I assert my rights and reassure them I'm an artist by explaining the "project" i'm working on and perhaps I'm a student or professor from the famous art college 10 blocks away.

jim10219 said:

buy a photographer's vest

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Thanks for your comments. Yes, like many people I probably have a self esteem issue. I have often called myself an anti ego.

But a photographers vest? You might as well draw a big arrow and say "look over here".

Saganich said:

Yes, this has always been an issue on the street. I adapted a shooting style for humans in the street that includes not putting camera to my eye until I'm ready to snap. That means everything is set before and I'm waiting for the right moment...however, standing still on the street corner is also problematic...so I tend to watch the street around me while walking around, spot a scene, set camera, and proceed to walk through the scene pausing briefly to compose, snap, smile like a fool, and keep walking...I think Winogrand did something similar... I avoid that which looks dangerous (young punks with guns, Hasidic men in packs of 4 or more) I find waist level finder point and shoot, any old folder avoids suspicion. When I have been confronted I gauge my response based on their level of anger. For angry people I assert my rights and reassure them I'm an artist by explaining the "project" i'm working on and perhaps I'm a student or professor from the famous art college 10 blocks away.

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Oh yes, we all know that Hasidic men in packs of 4 or more are known for acting gang members with guns.

I have issues in crowds, I always show up for my client shows, but I absolutely hate small talk and always end up in a corner by myself pinning to go home. I think I too would have a very
difficult time walking up to people and photographing them.

But what is weird I have zero problems doing talks in front of larger groups, I have always been amazed at this contradiction.

Self-esteem and self-conciousness are different, however complementary and probably linked things.
The former: Guard your integrity and know your strong and weak sides, the latter helps to correctly place yourself in a given situation (well, a bit too simplified).
I sincerely sympathise with Bob Carnie and like-minded contributors: In deed, why would I (we) invade the private sphere of a stranger to take a snap? I mean, whithout a declared genuine motive (but that of a thieve)? In deed, the normal sequence would be that a situation or person catches my interest, I'd judge whether time and context support "a closer look" or involvement, and the opportunity for a "good" picture may arise. With "good" I mean that it conveys the photographer's emotions and involvement in the situation besides info on the subject... (- for some types of documentary, other criteria may apply.)
Being sure about yourself and your right place in this endeavour certainly helps.
BTW, I find that nearly all "stolen shots" are less than interesting (from an emotional point of view, they may be funny/sad etc. but not really engaging the viewer), all good portraits I am aware of are based on an "agreement" between subject and photographer.
Thus, again, the "good picture" conveys the (emotional) involvement of the taker or maker, his/her interests and compassion, or sometimes loneliness etc. Interests and passion may even apply to documentary and scientific topics.
Just some short thoughts...

TheRook said:

Remedy:
Alcoholic beverage.

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Yes, but that always makes my photos blurry.