re: If your child self was friends with your kids would you think they were rich?

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So you didn’t do better than your parents even though you had all of those advantages?

Had I had just basic parenting, I would be a fricking mogul.

My kid lives a very privileged life, and I’m proud I could do that for her. She needs to move the ball forward and exceed anything I’ve done.

She has the ability and drive to do it.

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I do just fine, but my father struck lightning in a bottle with his career.

Everyone thinks if they had this or that growing up they'd be Elon Musk, but in reality outside of those that inherited a ton of money allowing them to take risks in their career, I don't think that's the case. The floor is certainly higher, but I don't think the ceiling is that much higher (outside of the inheritance situation).

And in some cases (not all), presumably like yours, the challenges you faced growing up allowed you to navigate adulthood with an edge privileged kids don't have. You might be rare in this regard, but that is a testament to you.

I have a couple of degrees (I paid for the second one) and my kids attend private school and get to do all of the sports and we have good vacations and they won't pay for college. But skiiing every year with international vacations mixed in and a full time housekeeper are not in our budget. Life is just more expensive now, even on a relative basis. It's wild how much those things cost now.

All that said, yes my dad made more money than I do, adjusted for inflation. But I am not some failure and think I used my privilege to set up my family just fine.