Our advice columnists have heard it all over the years—so we’re diving into the Pay Dirt archives to share classic letters with our readers. Submit your own questions about money here. (It’s anonymous!)
Dear Pay Dirt,
I’ve decided to basically cut off my daughter once she’s finished with high school, which will be just over five months from now. She didn’t do anything wrong, I’m not eager to be rid of her, and I could easily continue to provide for her basic needs, but I won’t. I myself lived with my parents into my 20s, but I feel like this did me no favors, and I’ve come to believe in “sink or swim” and “hard knock” life philosophies. So please don’t argue about this decision.
My only question is when and how to deliver this news to my daughter. I don’t want to ruin her birthday or the rest of her senior year, so I may wait until after graduation to tell her she’s on her own. I’ve been trying to instill frugality, budgeting, and saving, but my daughter doesn’t yet know how important that will soon be for her. If she knew now, she might be better prepared, but I can see how the stress from this might actually be detrimental overall.
My daughter and I have a tender, loving relationship, and I’m sure she will be surprised to find out she’s being turned away. Or maybe she will surprise me and fly the nest without being pushed. She actually told me months ago that I shouldn’t pay for college; that is actually what got me started down this road. I hope to still have a (non-co-dependent) relationship with her after this, but I will understand if she doesn’t speak to me for a while. Should I continue to gently lead my daughter toward independence without letting on that it will be forced? Or do I need to inform her now that she will be on her own come summer? Again, my decision is firm in that regard, so please don’t argue there.
—Tell Her Now Or Later?
Dear Tell Her Now Or Later,
A hazard of writing to an advice columnist is that you may not get the answer you want to hear, but a corollary to that is you can’t tell the columnist what kind of advice to give you. So here’s something you don’t want to hear: You’re creating a situation with your daughter that will absolutely harm your relationship with her, and potentially indefinitely. You seem to be aware that this isn’t going to go well, but you naively assume that it’s going to be a temporary rift, which means you misunderstand the nature of what you’re doing and also what sort of relationship you might have once your daughter is out of the house, and can never speak to you again if she chooses.
The issue is not that you want your daughter to be independent; that’s great. It’s that cutting her off abruptly with little or no warning makes some insulting assumptions about her—one of which is that if you don’t cut her off, she’ll be incapable of being independent. Maybe this was true of you when you were her age, but your child is not you. You are different people, and that should be clear to you because she’s volunteered that she didn’t want you to pay for college.
What you should do is have a conversation with her about how she plans to become independent once she graduates, and help her plan it. That is actually helpful, and you don’t risk making her feel completely abandoned by you for no reason other than your own guilt about living with your parents when you were in your 20s. As for sink-or-swim tactics: They work for some people, but they traumatize others, and sometimes when you throw someone into the deep end, they just drown. You have no way of knowing how your daughter will react. (Sometimes even despite their best efforts, people flail and drown.)
Throwing someone abruptly into a situation they may not be prepared for isn’t tough love, it’s just an unwillingness to do the work of helping them prepare. Even if she comes out of it OK, she will probably resent you for it, because it is a harsh tactic, and often deployed punitively. Why create that resentment when there are plenty of healthy alternatives that would make your relationship stronger? This is the kind of thing people talk about to their therapists years later, not because financial independence was too big of an ask, but because pulling the rug out from under someone with no warning is a breach of trust. As parents, we try to make our children feel safe while they’re with us so that they have the confidence and skills to live as adults, and psychologically that sense of safety is important, even if it’s illusory. If your daughter does have a good relationship with you and trusts you, imagine what it does to her for you to abruptly say, “By the way, you’re on your own, and I am not going to help you if you need it.”
It’s fine if you don’t want to support your daughter after high school, but don’t pat yourself on the back for good parenting, because this isn’t that. You need to actually talk to her and do it in a way that makes her feel like she still has a safety net, at least psychologically, if she tries and it doesn’t work out. Go ahead and tell her now, so she can mentally prepare. The longer you wait, the less prepared she will be, and if you do love her, surely you don’t want her flailing dangerously in the deep end.
—Elizabeth Spiers
From: I’m Going To Cut My Daughter Off The Minute She Graduates High School. (January 5th, 2023).
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Dear Pay Dirt,
My mother passed away five years ago and left her small estate equally to her four children. Her estate consisted of a house and about $40,000 in cash.
My mother had a long-term partner she never married. In her last few years, he moved in with her and helped care for her. For years, my mother supported her retirement by renting out rooms in her five-bedroom home. It was her hope that he could continue living in her house and rent out rooms. This would pay for maintenance, property taxes, and insurance and give her partner a place to live, as he has never really worked and lives on disability payments.
Unfortunately, this person is a hoarder and since her death has filled the house with piles and piles of stuff. The front yard is also full of stuff now. The house is so full he is only able to rent out one room, and he uses the rent from that room to support himself. The minimal payments we have asked for my mother’s surviving partner to pay (only $400 a month, just enough to slow the drain on the estate) have been paid less than half the time. The $40,000 that was originally in the estate’s account has dwindled to less than $20,000. The house, which my mother always kept clean and organized, desperately needs repairs and paint. Very soon we will no longer be able to cover the insurance and taxes, and there will be nothing left for repairs.
We are very fond of this person, and he has many wonderful qualities. We don’t want him to become homeless. However, it is not sustainable for him to continue living in the house without renting out rooms to cover the expenses. And I do not think that this person is capable of cleaning up to the point where the house can sustain itself with roommates. How can we address this in a way which treats our mother’s long-term partner in a humane way, but also protects our inheritance? He doesn’t have enough income to live on independently but also isn’t doing his part to sustain the arrangement.
—We’re Stuck Here
Dear We’re Stuck,
I say this with respect and love: Just because your mom wanted to take care of somebody doesn’t mean you have to. I’m sure he’s a nice guy, and your mom had her reasons, but that doesn’t mean you have to take him on, especially if he isn’t holding up his end of the bargain and is trashing the place. So you have two options. You can allow him to live there, with stipulations put in place, or you can evict him, but both of these options require you to meet with a real estate attorney, stat.
If you allow him to stay, you need to have a formal landlord-tenant lease agreement put into place. This is to protect you, your siblings, and him, whether it seems like it or not. He must abide by the rules put in place per this agreement or face eviction. This might be enough of an impetus for him to start cleaning the place, but it’s hard to say if it will work—it sounds like this person has a lot of mental health issues, as well as some physical limitations that may make this difficult. If you want to extend kindness even further, you might offer to help him do some of the initial cleaning—make it a project, while also making it evident that this is a transformation that has to occur, and represents the last stop on the way to eviction.
If you choose to evict him now, I wouldn’t blame you. Real estate laws are different in every state, and instead of taking this on by yourself, please consult an attorney. He has rights, due to having lived there for as long as he has, and the lawyer will need to walk you through the formal process to make sure this is taken care of in the right way. Godspeed, friend.
—Athena Valentine
From: My Mom’s Hoarder Boyfriend Is Ruining Her House. (May 4th, 2022).
Dear Pay Dirt,
My partner and I purchased a fixer-upper in December. The purchase price for the house was about $200,000 under our budget, but we estimated it would need about $200,000 of renovations to make it livable, so we figured it would all come out roughly even. We’re extremely lucky that a recent inheritance meant we could pay for the renovations in cash, but our plan was to get a home equity loan or construction loan for the renovation costs, given the super low interest rates.
Unfortunately, once we started the renovation process, it was clear that the timelines weren’t going to work. We needed to start paying for renovations in February to get the project at least somewhat finished before our move-in deadline in April, but when we started reaching out to home equity loan providers in January, we were told the loan process would take at least four months. We paid for the renovations in cash. While I’m grateful we had the cash to make the work happen on schedule, I’m bummed that the inability to get a loan for the work means that in the long run, we’re taking a substantial financial hit (I had planned to invest that $200,000). When we started the homebuying process, we made a spreadsheet with various purchase/loan/cash options, and we literally ended up with the worst long-term option.
At this point, is there any way to retroactively get a loan or something else to recoup those losses?
—This Is Fine, but Not Great

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Dear This Is Fine,
My Boss Asked a Question About My Potential Promotion. Uh, the Answer Is Obvious.
I Just Found Out That My Wife’s Aunt Has Been Lying to Us for Years. I’m Not Sure My Kid Is Safe Around Her Anymore.
I Did Some Good “Parenting” While Babysitting My Nephew. My Sister Is Furious.
I completely understand why you are in your feelings about using your cash reserve to make home improvements instead of a home equity line of credit, or HELOC, loan. You are lucky to have had the cash, but that doesn’t mean it stung any less. I might be missing something, but I believe you are asking if you can take out a loan to invest to try to get your money back in the market.
You can get a HELOC loan anytime after you purchase your home if you have enough equity and good credit. But it doesn’t take away from the fact that a loan is still a loan and it will need to be paid back. I do not advise you to go into any more debt than is necessary. Do not borrow against your house to invest. Any time you are investing, you need to be committed to keeping your money in it for as long as it’s needed to make a return. This can be up to 30 years.
I would chalk it up to a badly timed mistake and instead create a bare-bones budget to free up cash. Then once a month, make a deposit into a brokerage account with whatever you’ve saved.
—A.V.
From: My Entire Credit History Disappeared Overnight. (May 31st, 2022).
Classic Prudie
My husband and I have been married for a year and have a new baby. We were talking about abortion in the context of news this week when my husband casually asked me if I had ever had an abortion. I changed the subject. The thing is, I have had two abortions, both when I was a teenager. My husband is pro-choice, as am I, and I’m neither ashamed of nor regretful about my decisions. I’m not sure why, but I just really don’t want my husband to know. It was during a tough time in my life, and I would rather put it behind me forever. I know this is a big thing to keep from him, but would it be OK if I kept that part of my past secret?
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