I remember in 2004 when someone from my high school graduating class friended me on Facebook. I was recently fired from a telemarketing job, which I took after I left an ice company after only making $21,000 in annual earnings after working there nine years. I think the job I had at the time was basically similar to collections, excepting arguing with people to get car insurance on their cars we had their loans for. He had just graduated from Rice University's law school and was working as a lawyer at a local law firm. I felt pretty small at that time.
Another guy I graduated high school with with is an assistant athletic director at Butler University. Another is on the PGA tour (he also went to my grade school and I played soccer with him for seven years). A guy that graduated a couple years before me is or was on the Cincinnati city council.
But none of these people were friends of mine. I have two close friends that work in financials, one at a company as CFO and the other at Fidelity Investments. Both are doing quite well for themselves career and wealth wise.
I've long since learned to not let these sort of things bother me.