Help! I Told My Friend to Quit Her Job. Things Have … Not Gone Well.

 Dear Sarah,

I have been friends with another attorney for several years now. We both graduated from law school about the same time and practiced in the same field of law. During and after the immediate aftermath of the pandemic, her employer couldn’t pay a full-time salary and moved her to a part-time position. My friend was increasingly frustrated by this and her unhappiness soon dominated our conversations. Once it became apparent that this was not a temporary problem, I suggested that she change employers. She took my advice but in the year since then, she hasn’t been able to hold down a job. She has a good resume and hasn’t had a problem getting hired at good, well-paying positions in her field, but she seems to self-sabotage at each position. She constantly puts down her own abilities and, according to her, she often refuses to do things her employers ask, claiming that she doesn’t know enough to do them.

I find this distressing because, from my interactions with her, it seems like she does know enough to do these things and can pick up new skills with relatively little training, but she seems unwilling to push herself to do so. She also seems to have personal conflicts with people in each of the positions she has worked at, some of which sound justified and some of which do not. Throughout this time. I have tried to be supportive and offer practical advice when asked, but I don’t think I have done much good for her.

Recently, she has become very upset, as some of her relatives who had been providing her housing and covering some of her expenses have told her that they will not be able to continue to do this indefinitely and have advised her to start making arrangements to live on her own. My friend has been worried about her future since and has been catastrophizing. Now, she’s suggesting that she could move in with me. In the past, I had told her that she was always welcome to stay on my couch if she needed to, but this was always meant as a short-term solution to help get over a crisis for like a month or so. I really don’t want to have to take care of a 35-year-old woman indefinitely.

There will be a position opening up at my office soon, and I’m pretty sure I can get her hired if I recommend her. However, it is very similar to one of the positions she was recently fired from. I personally think that she can do it and feel like if I just assisted her in finding her feet with it it could work out. I asked her if she wanted me to put her name forward and she was non-committal and said that she didn’t think she could last at it and wouldn’t want to embarrass me I feel guilty that things have worked out so poorly for her after following my advice, and I feel the job could be a good opportunity for her, but I also don’t want to set her up for failure by pushing her into taking a position that she lacks the confidence to do. I also really don’t want a roommate at my age. Any ideas on how to resolve this?

—Bad Advice Giver

Jenée Desmond-Harris: Something I didn’t get to in my response: I wonder if they’re really friends, or just law school classmates who know each other and talk about career stuff together

Joel Anderson: That’s what I was wondering too. I know no letter can truly—or should—provide every detail but it feels like there’s a lot more intimacy than affection between these two, if that makes sense? They obviously have a relationship, but I can’t tell how close it really is, or if it’s just a case of two classmates who have a lot in common professionally but not much else outside of that.

Jenée: Yeah and sometimes people who … I’m trying to figure out how to put this delicately … people who are maybe a little bit emotionally immature, like the LW’s friend, can overshare in a way that makes you feel you’re closer to them than you really are. So LW should really take a step back and ask “Do we have the type of relationship that would reasonably make this woman expect to move in with me?” I think the answer is no!

Joel: We’re having to do a lot of projection here—so apologies in advance—but to build off of your point about emotional immaturity: I can even relate to the LW, as someone who’s sometimes been overly accommodating to a classmate or co-worker who is mostly harmless and really looking for companionship. But that dynamic can be really draining, and sometimes their problems can start to feel like they’re your own. And then you start to feel obligated to help out in ways that probably aren’t the smartest … like considering turning this person into a roommate.

Jenée: It’s a lot easier to continue to be nice when the friend isn’t leaving hair in your shower or late on the utility bill. This relationship definitely won’t improve with more closeness—and it won’t help the friend succeed in the workplace. I actually think what she might need more than anything is a career coach. If LW really wants to be generous and helpful in a way that won’t tie her to this friend in a stressful way, maybe they could help set that up.

Joel: Right, I definitely don’t think they need to take this relationship that far outside of the office. Recommending a career coach also helps the LW avoid having to provide a reference that she might not want to make, lest it make her employers question her judgment. Don’t welcome a known problem employee into your office at your own, unprompted suggestion! You can still help your friend—but if she’s got family members who are fed up and willing to nudge her out of their home, it’s unlikely that you’re going to fare better. At least right now.

Jenée: Also, LW, forgive yourself for telling her to change employers. You’re not a “bad advice giver.” Your advice would have been fine if she had, for example, not refused to do the work assigned to her!

Joel: Absolutely. If your friend had been better at the job, there’d be nothing to apologize for. On the bright side, even your friend seems dubious about whether this is a good fit. So just drop it, if you can.

Oh, last thing: Feel free to lie about being unable to accommodate a roommate because you need to keep a room or bed available for an unnamed relative or friend. You don’t have to offer her any more details unless you want to. The most important thing is to maintain some appropriate distance here.

Jenée: I get that because you’re not confrontational (and neither am I), but I think it’s also okay to just say “I really like living alone and don’t want a roommate.” Either way, LW, do what you need to do so that you don’t have to see her before you’ve had your coffee every morning. I wish her the best, just not under your roof.

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