Dealing With Success Guilt

[Andrew Hendrickson]

So I've always been the so-called "golden child" in my family — well that's what one of my friends says. Always planned to be the one to break out, I'm the one with the flashy experiences, the wide open opportunities, the one with ambitions.. And it's not just my family, but my friends are generally underambitious, under accomplished, not really going anywhere. 

In the last year do to well chosen stocks on a very aggressive strategy (after a decade of data collection I finally made a decisive move) I've increased my net worth from being slightly negative to being more than 1.5x my work income for the year, which was already higher than most of the people I know. That particular run hasn't fully played itself out yet (oil stocks, not GME, just if anyone was wondering), and then I plan on transitioning into other growth strategies including real estate. The point is, this year "made" me, in a way that life will never again be the same. I was already trying to chart a course towards financial independence, but this year moved me up a solid 5 years at least. 

My friends and family don't downplay my ambitions, they don't try to hold me back, and I can't just dump them because they are important to me and were there for me through my difficult experiences, and they're a part of me. 

But at the same time the experience gap is widening, and it's hard for me to say that it's because I work harder — because I'm as lazy as they come, just clever and lucky — or that I somehow merit it — because between us all, I'm the one with criminal record, etc. Even if my friends don't care on the large (which I assume most of them don't), I find myself feeling guilty for the way I seem to have "short circuited" the game, for leaving others behind, for being the standout.  

I'm curious if anyone else is able to relate to this experience at all, and if so how you've dealt with it.