Pay Dirt is Slate’s money advice column. Have a question? Send it to Athena and Elizabeth here. (It’s anonymous!)
Dear Pay Dirt,
I’m 45 and have recently sold the company I started when I was 25 for a large amount of money. I own a condo and can live for the rest of my life without working again. My friends have asked me what I’m going to do after I’ve sold the company and I’ve told them the truth: I’m not going to work anymore, although I want to volunteer for a non-profit organization. My best friend doesn’t seem OK with this. First, he started saying I was very young to be retired, and eventually our conversation turned into him angrily calling me “lazy” and “entitled.”
I might want to start another company one day in the future, but this is not my plan right now. I don’t understand what is wrong with being retired if I worked so hard to build my company and achieve my goals. I don’t come from wealth, went to university on a scholarship, and was basically eating cans of beans all throughout my 20s as I struggled to fund the company.
My friend comes from an upper-middle-class family, had his university paid for by his dad, and also owns a condo but his dad helped him finance that, and his father employed him for several years at the family business when he needed cash. I can’t understand how that makes me the entitled one. I fear my friend has harbored a secret resentment since our university days and we may never be able to repair this rift. On the other hand, he’s one of my oldest friends and I’m not sure I want to stop talking to him forever. What should I do?
—Young and Retired
Dear Young and Retired,
This situation has nothing to do with you and everything to do with your friend. In his mind, he might think he should be better off financially than you at this time in your lives (like he has been for most of your friendship), but now you’ve exchanged roles. It doesn’t appear like he’s struggling by any means. To me, it sounds like he’s just jealous of your success and trying to figure out how to get back in control of the situation by making you feel poorly.
Unfortunately, many successful business owners go through this same situation. Sometimes people in our inner circles end up being the least supportive of our choices. But true friends don’t talk down to you and tell you that you’re lazy after you spent years living off of canned beans trying to make payroll—they rejoice in your success.
It’s useless trying to defend yourself. He’s counting on you to engage so he can continue to fight for some invisible upper hand. So, instead, try to have one more honest, calm conversation. You can say something like, “Hey, I know we’ve been friends for a long time, so it hurts me when you say things like this, given our history. I’m willing to hear you out one last time to see if we’ve had a misunderstanding. But I won’t be talking about my career with you anymore.” This way, you’re making him aware that he’s done something wrong and are giving him the chance to fix your friendship. But remember: No one has the right to put you down, and you don’t have to accept it.
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Dear Pay Dirt,
I have a money ethics question. I work full-time at a lowish-paying job but live with my parents, so I am able to save. One of my closest friends also lives with her parents, and cannot work currently for health reasons. Thankfully, her parents can support her without financial strain, but she isn’t making any money. Due to our personalities/preferences, I am most often the one who makes plans, which includes booking any reservations, and I find myself wanting to fib when my friend asks me how much she owes me to split the cost of a meal or a ticket, to save her the full cost. If something costs $30, I might tell her she owes me $10 instead of $15. Recently, we made plans that will be quite a bit more expensive; if I am booking two $150 tickets, is it ethically wrong to tell her to pay me $100 instead of $150 and let her think the overall cost was $200? My instincts tell me this is harmless, but I wouldn’t want her to feel insulted if she somehow found out.
Dear Sugar Bestie,
I don’t think you’re technically fibbing in this case—or doing anything ethically wrong. People can have a hard time receiving and giving. Sometimes both! This feels like a good way around that. Plus, splitting the cost of a meal or a ticket doesn’t always mean you break everything down the middle—even if that’s what we may default to. For example, suppose everyone except you had expensive steaks and wanted to split the bill evenly. In that case, you’d feel uncomfortable and would hopefully say something (that’s a different Pay Dirt question for another time). Plus, sometimes people do split things based on income level. For example, if a wife makes more than her wife, she might pick up the tab more often or they might agree on an income-based split for bills. You’re still splitting the costs, just in what you view as a more proportional split.
Another method you might try in the future is asking her to cover something for you in lieu of splitting costs. For example, if you grab dinner, she can pick up the dessert tab or pay for coffee the next time you both hang out. I usually ask people to pick me up a drink at Starbucks. It’s a small cost, but it makes people feel like they are still contributing when I’m treating them.
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Dear Pay Dirt,
One of my neighbors just posted on one of those neighborhood apps with GoFundMe asking for money for a car repair. They say the car repair will eat up all of the money they put aside for their children’s Christmas presents. In general, I don’t have a problem with people making these kinds of requests, but I do with these particular neighbors.
They live in an in-law suite at their mother’s house and don’t pay rent or childcare costs. Both the parents make good money. They constantly order food delivery. I know it’s them and not the mother because the mother constantly complains about them spending money on food delivery. The mother hates it because the kids moved in under the premise of saving up to buy a house but they are nowhere near their goals and the mother thinks they should have hit that goal several years ago. Normally, this would be something that needs to be taken care of in private, but they made their money issues public by posting on the app.
I am debating saying something like, “In the future, you should speak to a financial advisor who can help you save for emergencies like this by learning how to cut out luxuries like eating out and food delivery.” A friend of mine thinks this is judgmental and petty. I think people deserve to know who they are sending their money to. At this time of year, some people are truly in need of even the most basic things and I know a lot of people in the community who think those people deserve help first. The neighbors are making it seem like they are actually that needy. Do you think it is petty for me to do this?
Dear Petty Neighbor,
I have an outstanding long-term memory when it’s time to be petty with someone, usually backed by so many receipts, that Whitney would be proud. But from one grudge keeper to another, keep quiet on this.
Yes, you might think they are scammers. But ultimately, you don’t know the whole story. Plus, I imagine what their mom has confided to you was told in confidence. You don’t want to betray her trust by airing out these details online. She continues to let them live there for reasons you and I might not even know. This is not your place to opine.
Posting that could not only cause issues for your friend/neighbor but will also make you come across as passive-aggressive, and that’s not a good look on an app you’re supposed to be neighborly in. If your fingers slip and you must type something, you can always say, “Wow, I had no idea. I hope things get better for you.” At least then they’ll know the neighbors who are familiar with their situation are out there reading and watching.
I’m 27, and my mom and I grew up very close. It was often just me and her. I’ve supported myself since graduating college, and she now lives about 25 miles away. In the past few years, she has started escalating simple questions into situations she can control. For example, once I asked if she had any jumper cables she could lend me to jump my partner’s car battery. She told me she was calling a tow truck to take his car to a mechanic. She assumed the car would be unsalvageable, so she was also booking a rental.