Pay Dirt is Slate’s money advice column. Have a question? Send it to Kristin and Ilyce here. (It’s anonymous!)

Dear Pay Dirt,

My wife and I grew up in solid lower middle class homes. We had food on the table and clothes on our back, but not much more. After we got married we decided financial security was a priority. Made a budget based on our take home pay, any overtime/bonus I got went into our emergency fund to make extra payments on our house or car loans to pay them off early. No loans? The extra money would go into savings. My wife’s second job was for “fun” money, like trips and vacations. We decided to wait on kids until we were financially secure. We paid off our first house, rented it to pay most of the mortgage on our second house, and did the same with our third and fourth houses. So now, at around 60, we have four paid-off houses, three of them are rental properties, no debts, about $500,000 (increasing) in savings/investments, plus our 401(k) savings and a pension.

The problem is our three kids (and their spouses), despite our best attempts, are financial idiots.

Our oldest bought a house a number of years ago based on his and his wife’s income including overtime. We got into a heated discussion with him about not doing this and the repercussions as overtime isn’t guaranteed. He told us to shut up and he would ask for financial advice if he wanted it. His company then added another shift and so no overtime and yes, they lost the house. He was upset with us that we didn’t help with by making their house payments. They untimely filed for bankruptcy as they also had a ton of credit card debt.

Our youngest has no kids but she and her husband are always buying the “latest and greatest, trips, dining out, and I think have no emergency fund, and despite having good jobs I think they are living paycheck to paycheck.

Our middle child, in early December, wanted an “advance” on their Christmas gift (we give each child $2,000) so they could afford Christmas gifts for their two kids. We said “no” and he didn’t speak to us for two weeks. Yet his son plays on a travelling hockey team and his daughter takes riding lessons.

After this last incident, my wife and I are really thinking twice on passing down all this money and assets to our kids. They don’t want our advice, have no interest in learning how to manage the rental properties (applications, maintenance, permits, etc…), and financial security doesn’t seem to be a priority with them. We have a feeling if our kids inherited everything it would be like the stories of lottery winners who are poor, and after winning they blow the money in a few years and are back to being broke.

All three were in good financial positions when they went out on their own as we paid for all of their community college expenses and half the tuition and all of their housing expenses when they finished at a four year school, so they were debt free when they graduated.

So, is there an expectation or requirement to leave our kids this generational wealth? If not, we would leave them something, but nowhere close to what they are expecting.

—Financially Foolish Kids

Dear Financially Foolish Kids,

It sounds like you and your wife worked hard and made smart, disciplined decisions. I get that your kids are making some questionable financial choices  — ones that you certainly wouldn’t make  —  but remember: The world they’re navigating is a lot different than the one you started in. Housing, wages, debt, childcare…everything adds up differently these days. It doesn’t excuse their mistakes, but it does make it a lot harder to recover from those mistakes and probably a lot easier to make them in the first place.

When it comes to inheritance, it doesn’t have to be all or nothing. And if you’re worried your kids will burn through a big lump sum, there are ways to build in structure without cutting them out entirely, like putting the money in a simple trust so they gradually receive funds over time, or keeping certain assets (like your rentals) in a managed setup so they get steady income instead of one giant check.

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So no, there’s no requirement to hand over all your wealth. It’s not like there’s some moral code that says parents have to fork over everything they’ve built to their children. But you don’t have to entirely cut them off, either. You can find a middle ground that reflects your own values, protects what you and your wife have built, and still gives your kids some support. Generational wealth only works if the next generation is ready for it. If they’re not there yet, you’re not failing them by being cautious. But it might be worth a conversation. It doesn’t have to be a dramatic confrontation (I would avoid calling them “idiots,” for example) but you can be clear and direct. Frame it around your values rather than their shortcomings. Something like, “We’ve worked hard to build this, and we want to make sure whatever we leave behind actually helps you rather than puts you in a difficult position. That means we’re planning to structure things in a way that protects the assets and gives you some long‑term stability.”

This way, you’re simply letting them know that your estate plan will reflect what you believe is responsible. They may not love hearing it, but it’ll be better to have clarity now, and it might help them start thinking differently about their own financial habits.

—Kristin

More Money Advice From Slate

Nearly four years ago, I found out my husband, “Chris,” was having an affair, and I filed for divorce. He sold the house (it was in his name), avoided me, and used a bunch of legal tactics to make sure I couldn’t afford to live there. He had family money and a high-earning job. I was working part-time to stay home with our kids. Chris wouldn’t even divorce after I asked for minimal child support. After we separated, I relied on family, including my cousin “Victoria,” who helped with childcare while I worked full-time. She had her own kids at home and generously watched mine, too, at no cost. Since Chris and I were technically still married, my income didn’t qualify for any type of federal benefits. I thought I was going to be stuck in this legal limbo forever. Then, last year, Chris and his girlfriend were in a car accident.

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