There are no positive connotations when it comes to the word bragging. To brag means to talk boastfully and roughly translated that basically means “To blow smoke up your own ass.” One of the most commonly used words in English conversation is the word “I”. We tend to spend a lot of telling others how we feel and what we think and there is a fine line between sharing information and bragging. If you have this desperate need to talk yourself up to others and make yourself seem important it means that you have the bragging bug and unless you actively stop yourself from boasting you are going to be that person who no one really wants to be around… Even if you can back up whatever it is you are bragging about there is another life skill you should probably teach yourself; humility.
We all want to share our achievements and accomplishments, but do it in a tactful, tasteful way. The best way to explain why bragging can make you look like a dumbass is to take a look at the example on Urban Dictionary. If you are that person who brings up random accomplishments just to change the conversation back to you and back to something you did ages ago then be prepared to be labelled “that jackass.” The only pearl of wisdom I can offer is that your achievements should be for yourself and they should, above all other recognition, make you proud of who you are and what you have done. When you start using those achievements to talk yourself up then you have lost the point of great accomplishments.