That's a deep and complex question! I try to make a conscious decision every day to stay focused on what I consider my own personal definition of success to be, and I imagine that everyone has their own version of what they would consider success to be.
As a society we are definitely geared toward some picture of success, in my opinion too often determined by the media and what others deem successful. I think people do this to gain acceptance, and also because success in and of itself is addicting and gives many people a sense of self worth, importance and belonging.
I have always been one to look at the "why not?" side of things and side with the person who is not in the limelight but showing great character or potential versus the popular choice. I like to look for potential and possibilities and build on that rather than follow along with the crowd.
I am not afraid to go against the flow for something I believe in. I don't put much stock in what some would consider indicators of success. I'm pretty unimpressed with the superficial indicators - I look deeper. And I have learned through life experience that how a person appears, the amount of formal education they have or amount of money they have has little bearing on my opinion of, and interest in the individual. It has no bearing on the respect I afford the person.
Oh - and to answer your question - yes I have been successful in the past by a variety of measures. I don't think about being a "successful person." I don't rest on my successes. I keep putting one foot in front of the other. Like Kenny Rogers said in his song about the gambler, "There'll be time enough for countin' when the game is done."