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[quote=Anonymous]I drafted an extremely long message but it wouldn't let me post the first time

I'm from a family that's almost billionare status and spent time around a few different billionaires.
Attended elite N.E. prep school and was in private school before boarding school (and had a team of tutors around the clock to make sure grades were good).

Growing up, there's so much staff constantly around you that these people begin to fade away and become like art on a wall. Security, drivers, groundsmen, housekeepers, butlers, nannies, and a chef just kind of blend in since they're around so much as a kid.

At boarding school I had a great time and there were a few secret groups like the Diamond Club (this is beyond niche so if you don't know don't worry).
That world is small. Gossip spreads like a wildfire and everybody knows everybody, even if you think there's no way, there's some connection.

There's always some type of connection. Whether through family, business, boarding school, vacation, etc. it seems as if everyone tends to go to the same places and knows the same people and rightly so.

I have a hard time making friends with people in my age group who I didn't grow up with / know from other wealthy friends. I have to either hide my wealth and limit the type of conversations I have to be more inclusive and if they do find out about the wealth they make it awkward and try to get me to pick up tabs or feel as if I can sponsor events (I can I just don't want to).

Furthermore, I work an entry level job since I'm fairly young and the people in the company aren't familiar with the amount of wealth (they do know I have some money though since my boarding school is listed on my resume) and again it's weird since I probably have more in assets at an entry level position than the entire company / my bosses.

The best is when a manager offers to pay and says one day I'll be able to afford paying them back or when I walk around DC and the strivers try to gauge you based on your outfit and the plethora of personal questions they ask which I will probably lie about. While may seem wealthy to a lot it's not. There's few real money here and a lot of UMC people here making 250k to a million a year think they're rich but really that's an inconsequential amount in the grand scheme of things.

I don't live off family money and don't really tap into it unless it's for medical or housing. I work a nice entry level job and live a pretty middle class life and the vast majority of people in my social circle and my day to day life in DC don't know / think I have money, but it's nice to know that barring a black swan event I'll be comfortable for my entire life.

I'm writing this because I feel trapped, I don't have anyone I can really talk to and open up about this and have a hard time even interacting with people in DC. I end up keeping in touch with a lot of high school / old friends and spend an enormous amount of time with family. There's so much strivers in DC that it's obnoxious and off putting. 
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