I would fathom a guess that you feel middle class for 2 reasons: 1. Your life doesn't fit in line with your expectations of upper class. 2. 200k a year in the

I would fathom a guess that you feel middle class for 2 reasons: 1. Your life doesn't fit in line with your expectations of upper class. 2. 200k a year in the Bay Area is, in its weird, sad way, middle class. 3. The feeling of "killing it" is pretty difficult to obtain when you are an ambitious person. But you are doing well. You are probably doing better off than most people, even in the Bay Area. I hope that you can find some peace within yourself, because the only person who can make you feel successful is yourself. It seems to me that you need to learn how to set trajectories for yourself with success outcomes that resonate with you.