Dear Prudence

Help! I’m Failing at the Job I Always Wanted. What Does That Say About Me?

Read what Prudie had to say in Part 2 of this week’s live chat.

Dear Prudence: Help! I'm about to quit my dream job.
Photo illustration by Slate. Photo by Thinkstock.

Mallory Ortberg is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat. 

Q. Suffering to make a difference: I’m a teacher, and I recently made the decision to leave my high-stress job in favor of returning to my previous role at the end of the school year. This year, I’ve worked in a special class for refugee students with gaps in their education, and although I love them, the behavior management and the emotional trauma of the children have sent me to counseling, and I struggle daily with feelings of failure. Next year, I’ll still be working with students from refugee backgrounds but in small groups, with less stress.

It has always been my dream to teach a class like this, and I feel like quitting is admitting that I’m not strong enough to do a challenging but worthwhile job. I’m not one of those special teachers who sticks it out, and I don’t care enough about making a difference to suffer for it. Isn’t anything worthwhile also hard? How do I live with this decision and what it says about me?

A: It’s not especially clear to me that you are quitting. You’re continuing to work with the same population of students, although perhaps not all of the same individuals, in a slightly different setting. Framing it in this way—there are special teachers who are capable of working with students who have experienced trauma and have particular needs, and there are nonspecial teachers who can’t—is not going to be especially helpful as you figure out strategies to teach your students as well as you possibly can, while also looking after your own emotional well-being.

I think the “feelings of failure” you’re presently experiencing suggest you may have placed too much responsibility on yourself, as if you’re somehow going to be able to single-handedly redeem someone else’s difficult or painful circumstances. That’s not your job! And if you think of your job as “suffering to make a difference,” as if you need to sacrifice yourself in order to redeem or fix someone else’s life, then I think you’re heading for further burnout as well as setting yourself up as a bit of a martyr figure, which simply won’t be useful for you in reaching any of your career goals. I wish you all the best in this.

Q. Money, hers, mine, and ours: I’ve been married to a wonderful woman, “Jane,” for 12 years. This is a second marriage for both of us, and our children are grown and on their own. We have arranged our money so that we have joint accounts, which cover expenses, savings, and investments, but we also have personal accounts that we’re free to use as we please. Even though Jane makes good money, she is frugal and her hobbies aren’t that expensive. I make a little more than her but have some expensive hobbies, so I do not have anywhere near the ready cash she does.

Over the years Jane has generously helped her family with financial emergencies using her personal money. My parents have had money problems since my dad’s retirement and recently came to me looking for help, but I just do not have the spare cash in my personal account. Unfortunately, due to social media and family gossip, my parents are very aware of how much Jane’s relatives have been helped, so they believe we helped Jane’s family but are refusing them. I’ve explained the difference, but they keep coming back to me saying, “You’re married! It’s all the same money. Those differences are just made up!”

I would like to help them, but it would mean either asking Jane for money from her personal account or taking from our joint savings. Do you think it would be all right if I asked Jane to help me help my folks? I have to admit, I’ve been somewhat disapproving of how much she’s helped her family in the past, so I’m going to look a little foolish here, but I can live with that because these are my parents.

A: It is fine to talk to your spouse about the possibility of sharing an expense! Yes, by all means talk to Jane. The two of you have been married for 12 years; it’s not unreasonable that you would at least have a conversation about pooling your resources as a couple to help your parents in a financial bind. It doesn’t mean that you two have to join all of your bank accounts tomorrow, but it’s a perfectly legitimate subject to raise with your wife of more than a decade. She may say no, of course, and in that case you’ll have to tell your parents that you simply don’t have the money right now, but it’s absolutely a legitimate subject for discussion.

Q. Assisted suicide etiquette: I just found out that a relative of a relative has opted for assisted suicide, and I support this person’s decision. This person, while not related to myself and my family, was always interested and supportive of me and my brother’s academic and professional endeavors, even facilitating connections and introductions for my brother. We would like to communicate our love and support, but we know they are not reading emails, and we don’t even know if they want to hear from us in this extremely personal time. My relative will be going to the memorial and sending our thoughts and prayers, but knowing we have a couple of days to communicate to this person what she meant to us, should we courier a card? What would it even say?

A: I think a card is a lovely idea. You can say that you love her, that you’re thinking of her, that you’ve always appreciated how thoughtful and kind she’s been toward you. You might also try to call or to check in with her caretaker (I don’t know if she has a friend or partner or relative who’s currently helping her deal with communication) to see whether she wants to hear from anyone or if she’d prefer privacy before she dies.

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Q. My past keeps haunting me: Seven years ago, I ended a long-term relationship and decided to go back to school full time while also working full time. During this time I ran into a guy that I had known years before in high school. He was a regular who frequented the café that I worked at. One thing led to another and we started a very enjoyable friends-with-benefits relationship. It worked well for both of us for over two years. Then I finished my degree, which gave me a lot more spare time, and we started talking about actually dating. My one hang-up about him was that I’m very into PDA, like hand-holding and the occasional kiss, and he really was not. But in all other regards, we got along great.

Then I found out from one of his friends that he had a long-term girlfriend of five years who had broken up with him just a few months prior. I was devastated and angry; he had never told me he was seeing someone. I ended things right away. I thought about telling the woman about it but decided that there was no point. I had actually met her a number of times when they came into the café—he had just said she was a friend and they never acted anything more than friendly. She, on the other hand, didn’t know about me.

So I moved on with my life. I now live 100 miles away from where I went to college and have a husband, baby, and job that I love. My job has an office staff of only eight people and we all work very closely together. Not only are our work lives close, but so are our personal lives. We usually all hang out at least once a month for a barbecue or a birthday dinner along with our families.

Recently we hired a new woman to join our office staff and we are all really excited—until I realized that she was the ex-girlfriend. Thankfully she didn’t recognize me and after a few weeks of me feeling embarrassed, I got over the urge to tell her. I figured the past was the past and there was no need to have it complicate either of our futures.

Last week she got engaged to her ex. Apparently in the intervening years they had gotten back together. Now I don’t know what to do. She has indicated that he will be coming to the barbecues and other get-togethers. I just feel like this is going to turn into a not-great situation.

A: The fact that the two of you will be working together in close quarters and she doesn’t seem to recognize you (not to mention the fact that they’ve subsequently broken up and gotten back together, which at least suggests the possibility that they have discussed his cheating and found a way past it) inclines me to agree that you were right to say nothing. If you think it’s at all possible, I think the best way forward is to be friendly but professional with your new co-worker, to limit your interactions with her fiancé if and when he attends those monthly barbecues, and to focus on your own happy life.

Q. Have bombshell, must drop: I’m in a long, slow breakup with my live-in boyfriend. It’s become clear our goals aren’t compatible and in the past few months his physical interest in me has faded to nothing. With our lease up in two months, I was hoping to part ways amicably. But last night while very drunk he said some odd things that set off my alarm bells, and I admit I gave in and peeked at his latest text. He is very clearly deep into a flirtation with a new male friend (I’m a woman), knowing it wouldn’t seem off to me to be hanging out with a new guy friend all the time. The messages included photos of this guy in his underwear (my boyfriend responded “hotttt”) and a discussion about how this guy’s “harmless flirtation” may have “crossed a line” with my boyfriend responding that crossing the line was good.

Whether or not they’ve been physical yet, it’s clearly headed that way. Knowing this, I don’t want to spend the next two months sharing a house with him. Moving now would be very financially hard on me, so there’s no way I can suddenly end it without him guessing I know. Do I tell him? Do I quietly seethe and break up for the originally planned reasons? Do I just come home from work tomorrow and ask if they’ve had sex yet?

A: If the two of you are in the middle of a “long, slow breakup,” why not stop drawing out the process unnecessarily and break up? If it’s not financially possible to move out before your lease is up, then is living short term with an ex really any worse than living short term with someone who’s your ex in all but name?

I don’t think you need to seethe about this, quietly or otherwise. You already had excellent reasons to end your relationship, and now you can add to the list the fact that your soon-to-be ex is already scouting for your replacement. Keep your contact with him to whatever minimum is possible after breaking up (obviously if you have to share a bathroom for two months some contact is unavoidable), don’t go through his phone again, and plan for a better future once your lease is up.

Q. Nautical nuisance: I’m an officer on a boat in the tourism industry. I love my job and value guests who come back year after year. Some have been spending their vacations with us for longer than I’ve been alive, and treasure our boat and business. One of these guests, however, took a strong and immediate dislike to me last year. I’ll call them “Chris.” I’m already dreading the week Chris will spend with us this year—last year, they spent the entire time insulting me to other passengers and crew members behind my back, snapping at me to my face, and at one point cornering me and haranguing me about my personal shortcomings. Not professional shortcomings, mind; Chris admitted that I’m good at my job, but had a problem with my upbeat, easygoing demeanor. Because I am a young woman in a traditionally masculine position of authority, I get pushback like this fairly often but never with such personal dislike attached. As a parting shot, Chris shouted at me in front of the entire boat for not being thankful enough for my tip.

My boss, the captain, is supportive but doesn’t see it as too big a deal—it’s one cranky passenger for one week of cruising. He suggests that I spend that week barking orders more forcefully than usual and let the snaps slide off, since Chris is a longtime patron who brings lots of other people onboard. Though I could ask for that trip off, I’d already planned on spending my allotted vacation at two weddings of close friends. How do I deal, professionally, with a weeklong guest with a grudge?

A: I’m so sorry that your boss isn’t offering any support in dealing with a demanding, boorish passenger with a sexist axe to grind against you. (And how odd that Chris has decided to spend their limited vacation time on a boat with a young woman they resent! Chris, why do you make choices that get in the way of your own happiness?) Just because you have to stay professional doesn’t mean you can’t push back when Chris tries to get a rise out of you. “Chris, I have to get back to work.” “Chris, that’s not appropriate to say to me.” “Chris, I’m not going to listen to you criticize my personal shortcomings. I’m going to go now.” If you have any supportive co-workers who are willing to help you avoid or minimize contact with Chris, I hope you can enlist them to look out for you and help you exit undesirable conversations during his week onboard.

Have you seen the end of The Talented Mr. Ripley? You can’t, of course, throw Chris over the side of the boat, but you may find it cathartic to watch in your room at the end of a long day.

Q. Ex-husband blowing me off: As Mother’s Day approaches I’ve been getting anxious about one thing. Every year since getting divorced my ex-husband posts “Happy Mother’s Day” on Facebook and tags his mom, grandmother, etc.—but never me, the mother of his child. I don’t get a text or verbal note either. One year I replied, “You forgot someone,” and he deleted the comment.

We have a pretty solid co-parenting relationship and during drop-offs with the kid we talk for a long time. When Father’s Day comes along I just don’t say anything to anyone, or I might post a generic “Happy Father’s Day” on Facebook. I don’t single him out and then exclude him. Am I taking this too personally? What can I do to get over this when it happens again this year?

A: Mute your ex-husband on Facebook. This is good advice for all days of the year, not just Mother’s Day. If the two of you have a solid co-parenting relationship and this is the one fly in the ointment, then I think you should let it go and find other ways to celebrate Mother’s Day on your own behalf.

Q. Moving: My long-term girlfriend moved from the West Coast to be with me, giving up her family, roommates, and job to be with me. We had been doing the long-distance tango for three years when I finally got the promotion and position I have been working for since I started my career. I also got to snatch up a brownstone in the heart of the city for a rock-bottom price. I told my girlfriend that I was tired of travel and that she needed to either move in with me or we needed to break up. It made sense then: My salary is five times what hers was, and her field can be applied anywhere easily. I promised to support her and buy plane tickets for her family and friends.

Everything was good for about three months. Then it was like a switch flipped, and my girlfriend became incapable of being happy. Suddenly she hated the restaurants she loved before, she didn’t want to go see anyone, she started nitpicking our home décor, and she quit the job she found here because “she wasn’t accomplishing anything.” She sits at home and putzes around online. When her parents came to visit at Christmas, she came alive. She was laughing and bragging about the city, playing tour guide. When they left, the spark went out of her. She has flown back to the West Coast three times in last six months. She denies she is unhappy and refuses to see either a doctor or counselor. She tells me she loves me and says, “I chose you. Why aren’t you happy I am here?” Our sex life is nil, and going to work is like escaping a rain cloud and finding the sun.

I love this woman. A year and a half ago, I would have told you this is the person I want to spend the rest of my life with; now I swing between feeling guilty I made her this way and resenting her for not being honest with me. I don’t know what to do.

A: See a counselor without her. The conversation you two need to have shouldn’t be an argument about whether she’s unhappy, especially given that she seems determined never to admit that she is, but whether you are. You’re not happy in your relationship because your partner is emotionally distant, argues with you frequently about little things, doesn’t want to accompany you when you spend time with friends, and is both dependent on you and resentful toward you for said dependence. That’s worth paying attention to, and that’s a dynamic worth naming honestly.

Q. Breakup: I broke up with “Ryan” when we were in high school. I was going to college and he wasn’t. Ryan still hung around with my younger brothers a lot. My brothers are now grown and out of the house, and unfortunately Ryan’s relationship with them still is going strong. One of my brothers even lives with Ryan and his girlfriend. This is very awkward for me when I go home. Over Christmas break, I came downstairs in my PJs to find Ryan and his girlfriend eating breakfast with my mother. (Ryan was helping my brother and stepfather work on a car.) It was very awkward, even more so because no one seemed to think anything about it, not even my mom. Ryan was not mean to me, but I feel like every time I turned around he was there.

I have started to date “Simon” seriously, and I want to bring him home to meet my family, but I don’t want Ryan there. I also skipped my recent family reunion because Ryan was driving my brothers there after work. When my brother’s birthday came up, I asked him to disinvite Ryan. My brother disinvited me instead! He said that Ryan was his friend, that he wasn’t going to let me dictate his relationships, and that I needed to grow up. I went to my mother and she took my brother’s side! She told me she was “disappointed in me for being petty,” then reminded me that my brothers have now been friends with Ryan for a longer period of time than we dated. I told her I was their sister and I should come first. I skipped the party.

Now my other brother’s birthday is coming up, and I got the same response—I’m invited but Ryan will be there. I don’t know what to do. I feel like I am being pushed out of my family. Simon tells me it is not a big deal, but it is to me. What can I do here?

A: I don’t think you are being pushed out of your family! I’m inclined to be sympathetic toward your brother’s position. He has developed a long-standing close friendship with Ryan, wholly unrelated to the fact that the two of you dated in high school, and it’s unreasonable of you to ask him to drop that friendship years later just because you’re starting to date Simon.

Ryan is not close with your family in his capacity as your former ex. That’s how they came to know one another, certainly, but at this point their relationship has grown and developed wholly independently. You don’t have to like Ryan or even spend much time with him, but it’s unfair of you to ask your brother to disinvite one of his closest friends from his own birthday party. I think you should apologize for asking your brothers to stop seeing Ryan, go to the party, say a brief and friendly “Hello” to him, and then spend time with other people you’d rather see who are also in attendance.

Q. Re: Money, hers, mine, and ours: If you’re going to ask your wife for money, do any of your expensive hobbies include items that you can sell for money? It’s not exactly fair to ask your wife to sacrifice her money when you’ve already blown all your money on your wants.

A: Thanks for catching this. I didn’t address the difference in their spending habits in my answer. It’s one thing to ask for help with a one-time shared expense, but if he can take this opportunity to re-examine his own budget (maybe the reason they have separate accounts is because Jane doesn’t want to be unduly burdened by his excessive spending), then I think it’s a good idea to start re-evaluating whether he wants to spend all his income on immediate hobbies versus setting some aside for times just like this one.

Mallory Ortberg: Thanks for the assist, everyone. See you next week!

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Mallory Ortberg, Slate’s Dear Prudence, is co-founder of the Toast and the author of Texts From Jane Eyre.