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 family grew up relatively poor, no fault of my parents, just the way it was. They are now both deceased. As an adult I (and my wife) have tried to be more financially responsible, living within our means and having a budget with some money set aside for an emergency fund and also a vacation fund which we use for our yearly trip to visit my wife’s cousin down south over spring break.

My 30-year-old sister is a spender, maybe to make up for what we missed growing up. Her marriage ended after not even a year when her husband found out the amount of credit card debt she had and that she was adding to it; he wasn’t going to be dragged further into debt with his name attached to it. She filed for bankruptcy a few years ago so her credit is shot, yet she spends, spends, spends, without saving anything.

She regularly gets in a bind with bills she can’t pay. She asks us for money, which we loan (not give) her with a signed promissory note and no more money is loaned until the previous one is paid off, which she has never failed to do so. Usually these loans are a few hundred dollars at the most.

Last week her 25 year old vehicle finally died, not surprising as it had been nickel and diming her for the past several years and her mechanic had repeatedly told her that with the rust and other issues the car was at the end of its life. So you would think she would have been saving for another vehicle, right? Nope. She went to the dealerships to find another vehicle, and she can’t get any financing due to her credit rating and having no down payment, so she can’t buy anything. She is borrowing a friend’s ca,r but they made it clear that it was only for a few weeks because the friend’s husband had surgery and can’t drive for two weeks.

She is now asking for a $5,000 loan from us to buy a car, or $2,500 for a down payment. We told her no, because any money we had available (our vacation fund) was already “spent” for our upcoming trip and we were not going to touch our emergency fund to make a loan. Plus, it would take years for her to pay us back. She said she will be out of a job if she doesn’t have a vehicle so it is an emergency (she works in another town so no public transportation is available). Plus, she said, it would be no big deal if we skipped vacation this year because we have went every year for the last six years. Again we told her no, and there was no way we were going to co-sign a loan when she asked about that.

My wife and I made a decision that we would absolutely never loan her money again, no matter how small the amount. I feel it is time she hits rock bottom financial wise, even if she ends up out on the streets because she lost her job and can’t pay rent. Am I too cruel in thinking this way? Do you think her inability to manage money is similar (though not as serious) to a drug addiction were I need to quit enabling her and she needs to hit “rock bottom” before she decides to improve her situation? I have heard of “tough love” when it come to drug addiction, can this be applied in this situation?

—Spendy Sister Hits Financial Rock Bottom

Dear Spendy Sister,

It’s incredibly frustrating to watch someone make the same mistakes over and over, and I understand why you’d draw parallels to addiction. However, there is an important distinction between addiction and bad money management, which is that there are entire industries built on nudging people toward financial ruin, from fraudulent bank practices to predatory lenders and other debt traps. I’m not saying addiction is free from its own systemic challenges, just that the forces pushing people toward poor money decisions are everywhere.

Your sister sounds like someone who never got a lesson in basic financial literacy. You’re right that some tough love may be necessary, and I agree that you should refrain from forking over yet another loan. She is ultimately responsible for her choices, and you and your wife have every right to protect your own financial stability.

The point is, sometimes it’s hard to make good choices in a system designed to steer you toward bad ones. So if you do want to help, I’d nudge her toward support that could actually help her change course rather than just temporarily fix her problems. She could probably use some help building a realistic budget, for example, or maybe you could help her look into a nonprofit debt counselor, like the Financial Counseling Association of America (FCAA) or American Consumer Credit Counseling (ACCC). Or maybe help her research cheap used cars or look into ride‑share or carpool options. The point is, there are ways to help beyond just giving her money.

But the reality is that she’s deep in a financial mess, and there will always be another “emergency.” She does have to learn how to navigate these situations on her own, and if people keep rescuing her, she has no reason to figure it out for herself. But you can point her toward resources so that even if she does hit rock bottom—the way many of us do when it comes to money—she at least has some direction to climb her way out.

Dear Pay Dirt,

I am having a financial conundrum. I am 43, and I make a reasonable income that is solidly middle class. I am married with three kids. One child is just a few years from college, and the youngest is in kindergarten.

My problem is that I am really just lost when it comes to how much I need to have saved. There are so many resources on the internet that I’m lost. Before kids, it seemed so basic. But now I am concerned about helping to pay for college and balancing retirement. We have saved some money for college, but not enough to get them out of college debt-free, and I feel guilty about that. There are also all of the costs of home ownership that I am balancing as well. Our roof is about to be replaced, and our two cars are 17 and 20 years old.

I just feel really overwhelmed and want a plan to follow. Can you point me towards a book or website I can trust that will give me milestones to hit and an actual plan? A resource that will tell me how much to save for college and retirement and a house repair fund?

—Middle Class Mayhem

Dear Middle Class, 

You’re in the same boat as a lot of us right now—doing our best to juggle multiple savings goals and priorities while we constantly feel squeezed in every direction.

To answer your question about resources, I find Vanguard’s retirement planning guides to be pretty straightforward and helpful, and they also have a very basic guide for juggling multiple financial priorities. I’d be remiss not to plug my own book, which I wrote for people just like you, but there are so many other great options out there, including The Index Card if you’re looking for a short and practical guide that covers some basic money rules that stand the test of time.
Generally, though, what you’ll find in your research is that your two big priorities should be retirement and household stability. Retirement comes first because most of us end up playing catch up in our later years, and that can lead to so many big picture financial problems down the road. I’m not suggesting you ignore college savings altogether, but you can relieve yourself of the pressure that it has to come at the expense of everything else. Most families don’t fully fund college, and if you’re going to put yourself in a precarious financial position to pay for it, that might just create more stress for your family in the years to come. There’s no shortage of rules of thumb for college savings, and a popular one is the 3 percent rule—aim to save that much of your household income per year, per child.

For home and car expenses, it might help to treat them as predictable rather than emergencies. Roofs wear out, cars need repairs, HVAC motors overheat. Set up a sinking fund where you put aside a set amount each month for that kind of thing. A common rule of thumb for a home maintenance sinking fund, for instance, is to set aside 1 percent to 2 percent of your home’s purchase price each year. Depending on where you live, that might seem like an outlandish amount, but of course, all of these rules are a ballpark, and there is no single magic number to save for each goal, because that number depends on your income, spending, and budgetary needs. The point isn’t to get it perfect, but to simply set up a system: save a fixed percentage for retirement, contribute what you reasonably can to college, and build predictable funds for inevitable expenses. Once you follow that structure, you can adjust the numbers over time. But the overwhelm tends to ease because you’re no longer trying to do everything at once.

—Kristin

More Money Advice From Slate

My partner and I are in our late 30s and have been together for a year. As we begin to talk about the future—living together, marriage, etc.—I am starting to think about our financial life, and I have some deep concerns. My partner has significant college debt, as well as a new car they are paying off on a zero-interest loan. They currently earn very little, as they are completing an education program (for which they took on a small amount of additional debt). They have no savings and no family they can turn to for financial assistance of any kind.

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