My Unhappy, Single Sister Demands We Pay Part of Her Bill on Vacation

My Unhappy, Single Sister Demands We Pay Part of Her Bill on Vacation

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Dear Pay Dirt,

My sister is (unhappily) single and child-free with a well-paying job. I only bring this up because I am not sure if it contributes to her views on this issue. She was engaged 10 years ago but they broke up and she hasn’t had a long-term relationship since, much to her dismay. She sometimes speaks negatively about her friends who have gotten married or been in long-term relationships.

When my sister travels with our family or with friends she insists on splitting the cost of accommodations by the number of people, so if she gets a hotel room with a married couple she wants to split it three ways. Our family (my wife and I, both women; my widowed brother and his young son, our parents, and my sister) take at least two vacations together a year: a ski trip in the winter and a beach trip in the summer. We usually rent a condo for the ski and beach trips with enough rooms for each person/unit. My sister insists that we split the cost six ways for each adult. I think we should split it four ways because doing it her way means she pays half as much as the couples do. For a $3,000 condo split her way our parents and my wife and I will be spending $1,000 while she and my brother spend $500. If we split it four ways, then my parents, wife, and I will be spending $250 less and she’d be paying $250 more, which seems reasonable since we are all getting the same amount of space.

I could see her point more if she had to sleep on a pull-out sofa in the living room because she was the only one without a spouse or children. She says it’s fair her way because the couples have two incomes but I don’t think that matters because who is to say those two incomes are combined more than hers? Or what if my wife or I decide to stop working and we only have one income? My family members seem to agree with me but my sister can act quite bratty when she doesn’t get her way. My parents just want all their kids together, so they also try to keep the peace, sometimes by just paying the difference. Before my brother’s wife died, they were strapped for cash with her medical bills and only one income so they wanted to split the cost per family but my sister was against it and so my parents just paid the difference. My wife especially hates this system and refuses to stay in the same hotel room with my sister. She’d rather pay more for us to have our own hotel room than to share one with my sister because my sister doesn’t compromise (like one trip we do it her way and the next trip we do it our way). My wife has even proposed that we get our own condo because we could spend the same or less than staying with my family. I proposed this to my parents last year but they got really sad because they like having all the kids together—plus, we do really like being together, it is fun to have a family breakfast and to play with my nephew. It’s easier for us to give in because my sister will just decide not to come if she doesn’t get her way.

I know my sister is being unreasonable by not being flexible or compromising, but also, are we crazy for thinking our way is a perfectly fair way to divide the housing costs of a trip for multiple people?

—What Is Fair?

Dear What’s Fair,

To me, it sounds like you and your sister both feel strongly about fairness but you have fundamental differences in what that looks like. You see a couple as being one person when splitting expenses and she sees you as two individual people. I can totally see how it’s easy to assume she feels this way because of a failed relationship, especially when hearing her complain about her friends. It’s shitty that her perception of fairness influenced her to treat your brother poorly in the past. But personally, I don’t think it’s unreasonable to split costs per person rather than per couple. A couple is two people, not one.

Think about it this way. Let’s say you went on a trip with three friends and charged an Airbnb to your credit card. It’s a gorgeous beach house, and it’s expensive, but you all are going to split it four ways because you’ll have your own rooms. When you arrive to check-in, you realize the beach house listing was wrong! You actually only have two bedrooms with one bed each, and the third room has two beds in it. But no biggie because you all will just share.

After your weekend at the beach, it’s time to pay up, and you Venmo everyone for their share. One friend sends you the cash you asked for, no problem. But your other two friends refuse. Instead of splitting it four ways because there are four of you, they want it split into thirds because they didn’t get their own room and feel they should now pay less. You would be mad, right? It’s not like you made them sleep on the couch.

If your budget is better off staying in a condo with your wife by yourself, then do what’s right for you and your finances. You can host family breakfast and still play with your nephew at the condo. This way you can give yourself some much-needed space and see if this alternative is a better arrangement moving forward. If you don’t want to do that, help your family find a place that is within your budget if you’re paying for it six ways. So if all you can afford is $200 a night, instead of getting a place that’s $800 get a place that’s $600. This way instead of arguing about money, you’ll just be arguing about who ate the last bread roll.

Dear Pay Dirt,

I need some advice on how to approach my manager/HR to ask about going part-time at work. I’ve only been here a year, but I’m completely burnt out. The job is great—I love my manager, have good benefits, and the work is interesting. But there’s definitely a culture of overworking and everyone automatically assumes every young employee wants to be promoted (I’m 28). Additionally, I have some pretty severe mental health issues: I’m in treatment, and the symptoms are mostly under control but are triggered by stress. I already have FMLA paperwork on file for this. I’ve been working nonstop with just the occasional vacation since I was 14 years old. I grew up very poor and needed to work a lot, but I’m in a much better financial situation now, with substantial savings, and a husband who does well financially, too. COVID just felt like the last straw, and I’m really done climbing the corporate ladder. I want to be able to work 20-25 hours a week and use the extra time to do the things I need to do to better manage my disability, like sleeping more, exercising, cooking food at home, going to therapy, and spending time with loved ones. I want to just stay in my current role, do what needs to be done, and log off for the day. I have no interest in being promoted.

I’m at the point where I’ll either quit or go on extended medical leave because of my stress level, and I really don’t want to do that to my understaffed team. I keep taking mental health days and they don’t work, because I’m just stressed about all the work I’m not getting done. I feel like I need a fundamental shift in my job, not just a vacation. I took a two-week vacation in September and it somehow made things worse because I came back up to my ears in work to do. I’d even offer to take a step down in title and pay to take on simpler responsibilities if it would make the transition easier. But I don’t want to sour my relationship with my boss, which is really good right now. Is asking to go part-time a reasonable request to make? And if so, how should I phrase it?

—Completely Burnt Out

Dear Completely Burned Out, 

It’s hard not to drink the hustle culture Kool-Aid when it’s everywhere you go. But it’s completely valid to prioritize other aspects of your life above your job. To protect yourself, and make sure your job is secure, I’d utilize your FMLA time and broach a conversation with your boss.

Asking to go part-time is a reasonable request to make, especially if you already have your health condition on file along with your FMLA paperwork. FMLA (Family Medical Leave Act) allows you to take up to 12 weeks of unpaid time per year to help you address your serious health condition, which can be used all at once or spread out per work week to permit a schedule change. Because you are asking to go part-time, your employer may need to reschedule your job duties to keep their company running. This can include an alternative work title with different responsibilities. Upon returning to work full-time, your employer must return you to the same job or at least one that is equivalent.

If you are still interested in keeping your position after returning from your part-time leave, come up with a game plan to see if it can be condensed into a permanent part-time role. For duties that can’t, have a suggestion ready to go about what department might be a good fit to take it over. Next, write a formal letter to your company about your request and ask to meet with your manager so that you can discuss your next steps. Indeed has a wonderful script you can use for letter-writing purposes. Your supervisor can review the next steps with you and then decide if you can move forward with a condensed version of your current position. If that’s not possible, you can then discuss alternative options.

The last thing to do is ask for a check-in period with your manager to review your progress in 60 days. This will give you some time to get used to your new role and then a few more weeks to focus on ensuring it’s the right fit for you. Then you can make a more clear decision about staying on as part-time or trying another option. Good luck.

Dear Pay Dirt,

I’m not really a “holiday” person. A typical year involves us doing a big, family gathering at Thanksgiving and a holiday gift exchange a few days before Christmas and the four (!) birthdays that week. Then everyone disappears until after New Year’s. My parents usually head to their cabin, my siblings visit in-laws, and my child goes off with their dad in another state. I’ve usually left here alone and take advantage of the situation to pick up extra shifts at work to make extra money.

This year for a few different factors, my parents have opted to stay home instead of going to the cabin. One of my sister-in-law’s mother is now living with them. All of a sudden I’m being asked/told about various things they want to do between Christmas and New Year’s. When I told them I was likely working (my schedule won’t be out for another week), my mom said that I was always working and that this was time for family. I don’t want it to be family time! I want to make money and take pressure off my co-workers who either really believe in the holidays or who want to spend extra time with their families. I’ve been happy doing this for 10 years.

How do I explain to my mom that while I value spending time with her and my brothers (I do! And I spend a lot of time with her during the year) my way of spending the holiday is working and that there will be lots of time for family things next year? Also if this will be a regular thing then I’ll make accommodations in a year. So far everything I’ve tried has led to a guilt trip or her saying that I don’t need to work extra.

—Work Is Plans!

Dear Work Is Plans, 

You’ve been respectful about how your mom has chosen to celebrate Christmas in the past, and you deserve the same in return. It’s unfair to assume that just because she has had a change in plans, everyone needs to accommodate her and do the same in return. Next time you talk to her on the phone, or if you feel brave enough to initiate the phone call on your own, say the following:

“Hi, Mom! I’ve been thinking about how you want to do a lot over Christmas break because you’re home, and that’s really great. This is the first time you’ve been home in over 10 years and I can tell you’re excited. I really want to spend time with you but before you made this decision, I already made my commitment. Spending time with you is important to me but it’s also important to me that I follow through with my word. Maybe we could do a family [insert activity] night either before or after that week? If this year goes well, and you’d like to stay home again, I’ll change my schedule for next year so I can be home, too.”

By saying this, you’re acknowledging she’s important and you understand where she’s coming from. But it’s also important she knows where you are coming from too. It’s not about making money (well, she doesn’t have to know that) but the fact that you are following through on your word, which is important. If she disagrees, you can say you respect her opinion and hope she can respect yours as well.

It’s also important to reinforce your boundary. So if she continues to guilt trip you, remind her that you will no longer be discussing it. Enforcing boundaries can be hard any time of the year so I wish you the best.

Dear Pay Dirt,

I am a man in my early 50s who was married to a wonderful woman who passed away a couple of years ago. We had a great life raising a child together, but we were awful with money. We didn’t save enough, spent way too much, and ended up with a great deal of debt. Soon after she passed, my mother did as well, and between life insurance and inheritance, I found myself unexpectedly well off. Over the last two years, I have paid all of our debts, sold our old house, bought (with cash) a brand new condo in a nice part of the city, and helped my child with his wedding and gave them a downpayment for their own house.

After all of that, I still have $800,000 in the bank, and it’s growing monthly because I make way more than my monthly expenses even after maxing out my 401(k) contribution. This is just sitting in a savings account because I have no idea who I should talk with about this. I am deathly afraid of reverting back to my previous paycheck-to-paycheck existence, but I also want to live my life and have fun. I know I need to talk with a financial advisor but have no idea who I can trust. How do you think I should go about looking for someone who can help me?


Dear Desperate,

I’m sorry for the loss of your wife and mother back to back. It’s commendable that you could turn your financial habits around so you didn’t repeat the past. Living your life and having fun can definitely happen, but you’re right. You would like to know how much you can reasonably spend without being left with nothing.

I recommend looking for a financial advisor who is a fiduciary. Fiduciaries are financial advisors who are required to always serve their clients with the client’s best interests in mind. There is no conflict of interest, so they aren’t going to be pressing you into unnecessary investments that they’ll make a commission off of. The Garrett Planning Network is a great organization that has a database filled with these types of advisors to help you find someone close to you. They also offer various free checklists in partnership with John Wiley & Sons to help you pick out the best advisor for you and your individual needs (for full disclosure, I am writing a book for the same publisher). I hope you get to enjoy retirement and your bright future.


Classic Prudie

A dear friend passed away somewhat unexpectedly a couple of days ago (she had been diagnosed with cancer in January, and although the prognosis wasn’t good, until a few days ago, everyone was still thinking in terms of years, not hours). I am sad, and my heart is breaking for her husband and daughters (both under 12). My issue is how to manage my sadness at the office.

#Unhappy #Single #Sister #Demands #Pay #Part #Bill #Vacation

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