My dad supports his sibling with monthly payments. I think my wife and I need that money more.

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

Dear Pay Dirt,

About five years ago, before he died, my father arranged to give a large amount of money each month to an ill sibling. This sibling and his wife have never been good with money. But they not only have a house that is twice the cost of mine, they sent their son to an expensive out-of-state university, whereas mine have gone to in-state schools. The sibling’s son has now graduated college, and my wife has what is usually a terminal disease. Between what the sibling is getting and his wife’s income, they make more than we do.

My father left no indication of his desires with regards to this arrangement. My mom says she is unhappy with the arrangement, but is afraid of confrontation. My wife and I do her taxes, insurance, take care of her house, and pick up the pieces after she gets scammed. This is becoming really hard to swallow.

—Getting Tired of This

Dear Getting Tired,

I get why you might be feeling overwhelmed and resentful. When you’re already struggling, it can be hard to sit by and watch someone else get a windfall when they’re already living better than you.

If your father didn’t leave a will or any formal instructions, this “arrangement” is in your mother’s hands. Clearly, he intended to help your sibling during his illness, but if their circumstances have changed—your sibling earns more than you, their son graduated, your own wife is facing a serious illness—it’s hard to say what your father might have wanted to do. You’re carrying a lot—emotionally, financially, and logistically, and you’re allowed to speak up about it.

It’s time to call a meeting and talk about this in detail with the rest of the family. You can hear everyone’s take on the situation, then leave it up to your mom to decide what’s the best way forward. This doesn’t mean you’re demanding that your sibling’s support be cut off, but you can express to them how this situation affects you and your wife. You might say something like, “We want to support you, but it’s hard to watch money go to someone who’s in a better financial position than we are — especially now  — and I think we should revisit how to share this money.” The conversation will be a lot smoother if you focus it more on your own circumstances than feeling envious about theirs. And you can all agree to leave it up to your mother to decide the best way to handle the situation.

Don’t think of it as a confrontation. This is just about fairness. You’re not wrong to feel the way you do, and you’re not asking your family for anything unreasonable. You’re simply trying to make sure that the support reflects everyone’s current reality, and that might mean shifting the inheritance. It’s a hard conversation, sure. But it sounds like it’s also a necessary one. If you approach it with compassion and honesty, there’s a good chance it could lead to a solution that feels good for everyone.

Dear Pay Dirt,

I’m 58, my wife is 54. Our three kids are grown and self-sufficient. We are debt-free and own our home which is worth around $400,000. We have a little over $1 million in our retirement accounts and roughly $100,000 in high yield savings accounts. In addition, I receive a small pension of $600 per month. Our problem is that it is likely I will lose my job next summer shortly after I turn 59. I would like to start working part time at that point and believe we will be ok as I can take my wife’s insurance and think we have enough in savings. My wife is worried that it will not be enough. We are moderate spenders with modest tastes. Our only goals in retirement are to enjoy some traveling and hopefully leave our kids a modest inheritance. Am I right that we should be OK?

—Too Early to Retire?

Dear Too Early, 

It sounds like you’re in a decent financial position. You own your home outright, you don’t have debt, and with over a million dollars saved, there’s a reasonable chance you’ll be able to reach your goals and live a pretty comfortable, if modest, lifestyle in retirement.

That said, your wife has a point. Let’s look at the math. Using the four percent rule as a guideline—a rough rule of thumb for retirement withdrawals—you could withdraw around $40,000 annually from your retirement savings, and with your $600 monthly pension adding another $7,200 per year, you’d have approximately $47,200 in annual income before factoring in any part-time work or Social Security payments. That said, you’ll also want to think about taxes, depending on the type of retirement accounts you own. You might not be living a life of luxury, but you can probably still afford a bit of fun, like travel.

But that’s if nothing major goes wrong—like big home repairs, medical issues, and so on. You might also live longer than expected, and you don’t want to run out of money. The point is, your wife is right to get ahead of all of these risks, so I would consider increasing your savings now, while you can, or looking for more income next year, or finding ways to reduce your lifestyle expenses so you can, again, up your savings. Chances are, yes, you will be okay. But I also understand your wife’s concern about living a bit too precariously in the face of things outside of your control. It would also be helpful to talk to a fee-only financial planner to help you run detailed projections and stress-test your plan against those unexpected expenses.

—Kristin

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