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I have an older sister and brother. We have a civil and loving relationship, but we are not super close. Recently, I've been getting the sense that behind the scenes there has been some jockeying regarding money from my parents. It bothers me to think that my siblings are doing this jockeying behind my back and I get upset and a little depressed about it every time I think about it. They are definitely more comfortable with the subject of money and more hungry for it. I have, over time, become a bit of a "hippie" and could see them using the excuse that I don't care for the money anyway, since I'm not as materialistic as they are. I don't know if I could leave it in my parents' hands to be fair about things: They are pushovers. Do I have to stoop to their level and start advocating for myself, beat them at their own game? Should I bring this up with my parents?


I think this is a question that is going to come up a lot in the drawing rooms and antechambers of the nation in the next few years.

I've read that there is a world-historical, intergenerational transfer of money about to happen.

Roughly, and anecdotally, the baby boomers are sitting on a massive, unprecedented stack of dough/real estate/other assets.

And of course anyone in line to inherit those stacks – well, it's kind of hard not to picture them like one of those old-timey cartoon wolfs: tongue unrolling onto floor, eyes popping out on springs, steam coming out of ears, "cay-oo-ga" sound in the background.

But that's not a good look for anyone. Personally, I feel it's sad, tragic, even pathetic to sit around waiting for someone to kick the bucket so you can inherit their bucket of cash.

I don't think my parents have much of anything – and even if they did, I wouldn't think about it. I want them both to live to 100, burn through all their money and leave nothing behind but a bunch of unpaid bills.

(Though, I will definitely hide behind the curtains when whatever bailiff/collection figure comes to my house looking for payment of said bills.)

The goal of life, I've often said, is to be a mensch (which doesn't sound like it but is in fact a gender-neutral term) and it is definitely un-mensch-like to be what one person I know calls a "waiter," i.e., someone waiting for their parents to die so that anvil of cash will drop down on you.

Having said that – you don't want to be a sucker. I've seen cases where one sibling has somehow wrested "power of attorney" over their parents' semi-substantial estate and suddenly starts sending their kids to private school, going on European vacations and so forth – while their siblings scratch their heads in puzzlement and poverty.

You don't want that. "Hippie" you may be and more power to you on that front. But "sucker/chump" you do not want to be, "sticking it to the man" while your fat-cat capitalists light their cigars off inherited hundred-dollar bills.

I would go to your parents. Sad to say, in older years, some parents King Lear-ify a little and can't always tell the difference between the Cordelias (loyal but less effusive) and Regans and Gonerils (treacherous but honey-tongued) in their lives.

So you may have to say something a little uncomfortable to them, to the effect of: "Mom and Dad, you know we love you to pieces and hate to bring this up, but have you considered what you're going to do with your money/real estate/other assets when you're gone? The last thing I'd like to see is a war brewing over something so mundane, which would sully your memory, and potentially tear this family, so painstakingly built, apart."

And I don't use the word "war" lightly. I know/have heard tell of so many cases of family who have gone to war over, say, the family cottage. One sibling winds up with it, but effectively loses all contact with the other siblings.

Which I think we can all agree is a crying shame.

So: yes. Approach your parents. It's not "stooping" to anyone's level. It's just being practical and think of it this way: Convince them, first, to draw up a crystal-clear will, making whatever arrangements they deem suitable and then perhaps convince them to announce whatever is the upshot of those arrangements to all and sundry so there is no further unseemly jockeying going forward, while they are still alive and everyone can relax and just enjoy each other's company without dollar signs in their eyes at family gatherings.