I think when I was younger, I sometimes managed to bluff my way through certain situations, because I knew I wasn't up to the task and played to my weaknesses. For instance, with women, I never tried to be macho, or attempt the typical male attitude about ANYTHING, because I knew I didn't have it in me. Not even a little bit. No swagger, no smoothness, no confidence in my natural charisma, because I had none. I was kinda cute, but it took me years to figure THAT out and even when I did, I had no clue how to use it to my advantage.
So I made the most of what I was - intelligent, funny, creative. I was Chandler Bing on the outside, and Ross Geller on the inside, and once in a great while, that worked for me. The rest of the time, it was boyishly attractive, yet repellently pathetic and needy. But dammit, I put myself out there and tried.
Now, that I'm older, I still underestimate myself, I just do it at home, cowering in a dark, lonely corner.
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"I don't mean to sound bitter, cynical or cruel - but I am, so that's how it comes out." - Bill Hicks