Pay Dirt

I Want To Take My Friends on Free Vacations. But I Have One Big Worry.

They don’t know how wealthy we are.

A woman looks fretfully at her credit cards.
Photo illustration by Slate. Photo by SIphotography/iStock/Getty Images Plus. 

Dear Pay Dirt,

My spouse and I both work well-paid full-time desk jobs. We are both naturally savers, and have lived under our income for two decades while minimizing lifestyle inflation. We make 10 times the median household income of our city, but we are not generally flashy spenders. I drive a 17-year-old car and shop at local thrift stores. Our friends probably suspect we are well-off, but they don’t know the details. We are fortunate to have a significant amount of disposable income monthly and would like to spend it on travel and entertainment. We can easily afford to bring our children’s friends, or our adult family friends, along on our monthly mini-vacations. Examples would be a weekend at the local amusement park with platinum-level passes, or a short stay in a pricy tourist town a few hours away. It’s more fun for our kids to have friends there, and we prefer to have other adults along too.

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I truly want to have our friends enjoy these experiences alongside us. But I know the other families cannot afford to reciprocate in kind. I don’t want or expect them to! How can I invite them in a way that would encourage them to come along without creating an awkward imbalance in our friendships? (We are debt-free; donate generously; and have covered college, retirement, and other major expenses. This question is about disposable income.)

—Multimillionaire Next Door

Dear Multimillionaire,

I think your friends may already have an idea of your generous personality—but you’re right. There is a difference between picking up a dinner tab, versus picking up a vacation. I think starting small, while coming from a place of excitement, will go a long way.

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Share that you guys were able to grab a great deal on passes at the local amusement park, and would love to treat them if they can join you. If they hesitate, say that you value their friendship, and you would love to share this opportunity with them. If they agree to your generosity, allow them to contribute however they see fit. Whether that’s picking up a lunch tab, or watching the smaller members of the group while others ride a roller coaster, allow them to do it. This is their way of reciprocating their love and friendship back to you.

If they decline, share that the invite is always open, and then move on to suggesting another activity that is lower cost or free. Your friends will see that you want to spend time with them no matter what, and it will lessen any awkwardness that may pop up. You can always invite them to more pricey events later on down the road, and who knows? Maybe one day they’ll take you up on it!

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Dear Pay Dirt,

My father died in 2016. After he and mom divorced, our relationship was extremely strained; I was only 8 years old at the time. We had an on-and-off father-daughter relationship, and at the time of his passing, we were not on speaking terms. I was actually very surprised to know that he left me anything in his will. My older half-sister, who I had a great relationship with, was the executor. My older half-brother was not happy that he was not. It made sense that he wasn’t—he constantly used my dad as a piggy bank, always with his hand out claiming he was “owed” everything that my dad gave him.

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My dad had two houses, a piece of land where he once ran a used-car dealership, a classic car, and some personal items. He left one house to all three of us, one house to my sister, the land to my brother and myself, and all remaining property and car left to all three of us.

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My brother wanted to reopen the business; I did not. I didn’t have the money for the taxes and repairs to the building, nor would I ever want to go into business with my brother, who couldn’t rub two pennies together. He cried about how that was what he wanted to do, that was going to be his retirement. So I allowed him to buy me out. The ink wasn’t even dry on the contract before he put the property up for sale for triple what he bought me out for, so he could collect all the money for himself. That’s the person he was. As heartless as I may seem, I did not cry with the family when my brother then died; because of this, my family disowned me.

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Now, the classic car and my dad’s personal belongings are still in the possession of my sister. According to the will, everything was to be sold and all proceeds split between us. With my brother gone, the will states that all remaining proceeds are now 50/50. What hurts is that I did nothing to my sister—I defended her when my brother was talking trash about her for “kissing up to dad” to make her the executor. I am lost at this point because I have other family members saying I need to pursue what is rightfully mine in the will, but I know this will also cause further tension with my sister, and our relationship may not be mended. What do I do?

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—So Very Lost 

Dear So Very Lost,

Grief is different for everyone. While you did not publicly grieve for your brother, that doesn’t mean you are heartless. I think the harder part of this whole decision for you is not asking for what is yours—it’s having your once-great relationship with your sister dissolve before your very eyes. What we resist, persists; until your father’s estate is taken care of, the situation will cause you additional stress, which you don’t need.

Instead of taking her to court, write her a letter and send it certified mail. This may seem like a perfect time to remind her of everything you’ve done for her, but it’s not. Instead, you could say that you are sorry your relationship is currently in this state, and that you are open to trying to make something work, after you both have had your space. But add that in order to give you both the space you need, the estate must be settled, so that you are no longer feeling forced to interact. You can then ask her how she would like to proceed, and you can suggest an  alternative dispute resolution (ADR), which is a way to dispute legal issues without having to take someone to court.

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One popular way to participate in an ADR is to hire a mediator. A mediator is a third party that will bring together all parties involved in a professional setting to discuss the matter at hand. Once both sides have given their uninterrupted account of events, the mediator can recommend a resolution so that both parties can settle outside of court. If your sister does not agree to move forward with an ADR, it would then be best to consult an estate attorney in your area to figure out your next steps.

Dear Pay Dirt,

I am a single mother of two, and I have lost a career job once a year, every year, for the past three years. In 2019, the company I worked at for a decade closed my division and gave us all two weeks’ notice. I picked up the pieces with contract work and struggled to find another career position. Then COVID hit, and I lost all my contract work. In late 2020, after living on food stamps and placing everything I could into forbearance, I got a position that lasted less than a year (again, due to COVID). During this three-year stint of repetitive unemployment, I have accrued nearly $20,000 in credit card debt and another $9,000 in tax debt due to incorrect withholding for self-employment. That’s on top of a $159,000 mortgage, student loans, and a car loan.

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Finally, after months of looking, I have a new career job that makes $71,000 per year. I am ready to address my horrific financial state, but I do not know where to begin. While I know how to do a monthly budget, I do not know how to begin paying back everything I owe in a way that doesn’t leave me destitute. I want to get to the point where I can handle an unexpected bill without having to fall back onto a credit card that I can’t pay off in full. Where, and how, do I begin to put my financial life back together? Is there anyone who can help?

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—Picking Up the Pieces

Dear Picking Up The Pieces, 

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Kudos to you for staying resilient. None of this sounds easy to handle, and you’re handling it while being a single parent. Feeling overwhelmed at where to start is valid, but I am a firm believer that you can do it.

If you are looking to streamline, you can consider a debt consolidation company. A debt consolidation loan is a private loan that is given to you by a bank to pay off all of your individual debt. So instead of owing ten different financial institutions a monthly payment, you now are only responsible for one. But depending on your situation, debt consolidation may not be worth it, because your credit score can tank in the process. You may also not be able to consolidate as many debts as you may think.

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Instead of debt consolidation, you could do the following. First, you need to make sure you have a place to live, groceries, utilities and a way to get to work. Then we need to create a way for you to have a buffer, so you can stop using your credit cards. See if you can refinance any of your debt for a lower monthly payment. If you’re not able to, call your lenders to see if they will provide any additional relief or assistance while you get back on your feet. Allow your student loans to be in forbearance while you work on making sure your basic needs are met and your housing and transportation is covered. If your budget can allow it, make sure you are making minimum payments on your credit cards so that you are not hurting your credit score.

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Start looking for another contract job that you can do during the evenings when your children are asleep. Every additional dollar you bring in can be put towards an emergency fund to help break the credit card debt cycle. Once you have a month’s worth of living expenses saved, I would then start throwing money towards your credit cards. Use the debt snowball approach— financial wins will keep you motivated to keep going. I believe in you, Mama Bear. You got this!

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Dear Pay Dirt,

Shortly before the pandemic started, my sister and I bought a vacation house together, as an investment and as a way for us to have a “family house” to gather for holidays. This turned out to be good timing in one way, as the real estate market in the area where we bought the property has since gone through the roof. The house is already worth a lot more than we paid.

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The pandemic has also meant that nothing else about our plan for the house has worked out. We’d originally planned to rent it out 50 percent of the time, to help cover the mortgage payments, and then split the remaining time between us. But my sister ended up being out of work for 15 months, and had to give up her expensive apartment in the city and move in to the vacation house full-time. Most of the renovation work has had to be put off, though we did manage to upgrade the exterior. I’m grateful that she had a safe place to land—she’s my sister and I love her! But as a result of her living there, I haven’t been able to use the house the way I’d hoped to. I’m paying for half the mortgage every month, and it’s starting to become a burden with no real upside for me. I’m also starting to resent the whole situation, which hasn’t been great for our relationship.

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My sister now says she wants to live there permanently, and buy me out. She doesn’t want to move again, and she’s fallen in love with the house. I don’t think she can really afford to do this. She says she can refinance, and give me a lump sum, but her income has been so low for the last year that I can’t imagine she’d get very favorable terms. I’m also concerned that this route would mean I’d end up with a lot less money than what we could both get if we just put the house on the market. Most houses in this area are now subject to bidding wars.

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Should I let her try to buy me out, or insist that we sell, and then she can get her own place with the proceeds? I know she doesn’t want to move again, but I suspect we’d both be better off financially if we sold.

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—Property Sisters

Dear Property Sister, 

It’s great that you care for your sister, and that you let her move into the vacation rental property when she could no longer afford her apartment. But you’re absolutely right in wanting to get out of this property now that the original investment plan no longer makes sense.

Give her the chance to refinance the home, and buy you out at current market value. Hire a professional appraiser so that you can ask for what the home is worth right now. This way you can still make the profit that you want, while allowing her to keep the property so she doesn’t have to move. If she can’t afford to buy you out, you have two options. Allow her to rent the home from you, or start the legal process to file for partition of the property. A partition of property, commonly known as a partition sale, will allow you to legally terminate your interest by forcing a sale. If your sister still cannot afford to buy the property in full, it will then move on to be sold to a third party. But beware that a forced sale may not be as fruitful as you may think, since the property could sell for a much lower amount than you wanted.

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If this is a route you are open to taking, make sure it is clear in your communication with your sister, so she’s not caught off guard if her mortgage application does not go through. I wish you and your sister the best of luck in finding a solution that can work for you both.

More Advice from Slate

My eldest daughter will be applying to colleges this year, and on her list are (almost exclusively) very expensive schools she can almost certainly get into. We’re in that tricky financial spot where we cannot possibly pay full-freight at these schools, nor are we sufficiently poor to qualify for the (excellent) need-based aid that the Ivies and some other colleges offer. I feel like I have failed her. We can send her to our decent state university, or she can take out loans, or we can take out loans. How can we explain this to her?

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