My recurring income right now is no where near what he was getting when he retired from the bench in 1998 (corrected for inflation.) He passed away in 2005 leaving several properties. I’m still mortgaging the only one I have. He left substantial cash both from savings and retirement benefits. I am one of seven beneficiaries, including our mother, and I have enough troubles raising just one kid.
Just taking a break from work.
I think you may be comparing apples and oranges. You say, “…when he retired from the bench.” So I’m assuming you’re early/mid career comparing with the end of a career. Also, it really depends on the job. I think my kids will have the same issue–I’m an engineer, they will both be teachers. They will not have the same standard of living at 50 as I now have. Its what they are happy doing. Both could have been engineers or accountants, but they would have had to work hard at it–the math and science didn’t come as easy to them as it did to me. My son enjoys history, my daughter enjoys working with small children. They won’t be pulling in the cash, but they will be doing what they enjoy
Good one. Still, I have to be honest with myself. I’m not as talented as our father. He was a muddy-footed farm boy and he made judge. We were raised in a middle-income environment, the advantage of which no kid can comprehend. Best we could do, as you pointed out, is to do what we like to do and be the best at it. And thank the old man while he’s still around (unless there are other big issues in the home.)
And we all know that money is the only important thing in life, right?
You said it.
There is another way to look at this.
He was rich, while raising kids and perhaps putting them through school.
But that doesn’t necessarily mean he was rich enough to set up all (seven?) of his ADULT heirs to be rich as well.
I had several friends who came from money - one from a LOT of money - and now that they are older, not one of them comes close to having the money their parents had. In part because they didn’t become doctors/lawyers (like their parents) and in part because the money they inherited set them up with a house and maybe some small investments, but nowhere near the lap of luxury they had been used to.
He retired from a bench?!
I hope to retire to a bench, hopefully one with decent padding. 
Well considering the salaries for even the bench-warmers in the NFL my guess is he made some pretty fair coin.
I think we mostly kinda assume we are going to do as well as, or better than, our parents. Often because our parents may have done a little better than their parents. And we tend to remember how we lived when we were in high school, when things were rolling along, rather than remember how things were when we were very young and our parents were maybe just starting out and struggling more. Like a lot of kids-of-some-privilege, we don’t have a sense of the work or struggle our parents went through to get to a comfort level. We just think that comfort is the norm.
Well, it’s not.
Just like a ball player who starts out “good enough”, then has a stellar year or two, and descends back to “good enough”, we always think that the stellar is the norm, and the good enough is somehow the anomaly. We attribute the early “good enough” to being a beginner, and the later “good enough” to the normal decline due to age. We over emphasize the success, and de-emphasize the lack of success. However, the real story is that “good enough” is the norm, and stellar is the anomaly.
It’s the same with life. Comfort is not the norm, it is the anomaly.