Not exactly taming the shrew, it's more like tolerating her.
January 6, 2008 9:06 AM   Subscribe

My very emotional former boss has become my friend. Please help me learn how to deal with her/mine/our issues. Long explanation follows.

Alright, so I worked there for eight years. A year or so after I started, my manager decided to retire and trained me to take over almost all of her duties as well. She retired and suddenly, I was spending most of my time with the owner of the company, right across the desk from her, every day, and I was the only employee. I got a lot of on-the-job training, and I also became her very close friend.

With every day that passed, more responsibility was shifted onto my shoulders. After three years or so, the situation had become strange, although I didn't realize it, based on my limited experience in situations like this. Every morning I woke up and within twenty minutes she was calling, asking when I was coming in, letting me know what she expected of me, what the highest priorities were that day (this usually changed overnight and sometimes duting the work day) and I was on 24-hour call every day of the year. She called me on more than one Christmas to wish me a merry Christmas, but she followed it up with, "well, I wasn't going to ask you to do this, but since you're already on the phone..." It was difficult for me to just not answer the phone. We had last-minute crises, that she seemed unable to handle, and when I missed an emergency call, she would guilt me for months afterward. I expressed to her that I would never do anything to willfully harm the company or her, and she would say, "oh, I know. I'm just mentioning this bad situation because of how it's affecting us now, etc., etc." I fluctuated between feeling guilty and feeling manipulated and used. She was completely computer illiterate, and insisted on me handling all of her paperwork as well as my own, but she critiqued everything, down to every single word, but she was indecisive on what to write instead, to the point that we would spend more than a half-hour writing a single paragraph email. She was an extreme micro-manager - she would ask me to do something, and not thirty seconds later, as I was doing the task, she would ask me if I had finished it yet, and here's something else to do right now. On top of it all, I had no benefits, no sick/personal days and my pay was always just a few dollars above minimum wage. [She thought my pay was right in the middle of what was fair for what I was doing, regardless of the fact that I was working about 3 jobs every day.]

Upside: she was flexible with my time, she was sometimes understanding and she bonused pretty well, although not reliably. I eventually fought for and got sick pay, and I got raises, but it was based on her "feelings" of my productivity and not my actual productivity. [She didn't know everything that I did throughout my time there to make that office run, and she never tried to figure it out. Also, I never knew if I would be able to afford Christmas presents, for anyone, even my kids, until the absolute last minute. Some years the bonuses were huge, and some years the bonuses never came.]

Fast forward five years. The week before this Christmas, she got nervous and antsy, and she made me antsy. I began to snap at her, almost without being able to control it, and she snapped back and asked me why I was angry with her. All of my explanations were met with "I didn't say that, and I don't think that I could ever say that." I got frustrated and eventually walked out.

The company is in its busiest season right now, possibly the busiest since I started there, but I'm at a point where I can't turn back. I've looked into some other jobs, and I've been offered nearly double what I was making with full benefits and a third of the workload. I worked with her yesterday, to finish end of year taxes, and she broke down crying several times. She's also been crying on the phone. I can understand that she's in a bad spot right now, and that she's stressed. But I think that I'm being manipulated all over again, and I don't want to go through that again. I also don't want for her, as a friend, to feel that I don't care about her.

How can I express to her that I need to move on, but that I still want everything but the best for her? I've tried, but it doesn't seem like she believes me. Am I just being manipulated into coming back?

(Yesterday I went back to take care of employee and contractor taxes. I need to do my personal taxes, and I've already been contacted by several of the contractors for their info. I see yesterday as much for me as for her.)
posted by mitzyjalapeno to Human Relations (23 answers total) 1 user marked this as a favorite
I think the best way to express it to her is in your formal letter of resignation. Either mailed or quietly placed on her desk with a brisk walk out the door. (keep a copy for your records)
posted by spec80 at 9:14 AM on January 6, 2008

Leave first (as coolly, calmly and professionally as possible). Repair relationship (if possible) after the leaving is done.
posted by winston at 9:15 AM on January 6, 2008

You quit. The job and the issues of this woman are not longer your responsibility. Do not capitulate. You do not owe her anything.
posted by miss tea at 9:15 AM on January 6, 2008 [2 favorites]

I also don't want for her, as a friend, to feel that I don't care about her.

She doesn't seem to be showing you the same courtesy. There's no reason to be mean, but stop worrying about hurting her feelings and focus on making the career decisions that are right for you (which, I agree, sound like they should include an immediate formal letter of resignation).
posted by occhiblu at 9:18 AM on January 6, 2008

Best answer: I take it you are both women. You are not the caretaker for your boss. This is a business arrangement that has outgrown it's usefulness for you and you already know you need to move on. She is leaning on you too much and leaving will be good for her, too, because it will force her to become a little more organized and maybe a little less sloppy with the emotional burdens you two have between you.
posted by 45moore45 at 9:21 AM on January 6, 2008

Best answer: Also, it sounds here like you're calling her a friend based on her having maintained a pretext of sociability (calling you on holidays) in order to manipulate you into doing more work for her, all the while not giving you the pay, benefits, or stability that a good boss should. You may be leaving out huge portions of the relationship, but a boss calling you on Christmas to assign you extra work does not really fit most definitions of "friendship."

I have been good friends with a lot of my bosses. The friendship part of that involved laughing over glasses of wine and dinner, emails about social events, fun lunches, and conversations about both of our lives -- not unexpected frantic phone calls every morning dumping extra unpaid work on my lap. It feels a bit here like you're trying to justify your capitulation to this woman's manipulation by calling it friendship; that is, maybe you're focusing too much on the social aspects of this relationship and not enough on the financial/career aspects of it. Not to get too gender-theory, but I think women are really trained to do that, to maintain harmonious relationships, and I know that impulse has made me make some stupid career choices -- because work, at least in our current economy and society, is one of those areas in which you really have to watch out for yourself more than you're watching out for other people. It's taken me a while to learn that, but doing so has cut down on the office drama a great deal and let me figure out what I really wanted to do with my life, rather than feeling like it was my duty to be at the beck and call of others.
posted by occhiblu at 9:26 AM on January 6, 2008 [5 favorites]

Response by poster: Yes, I am a woman, and there is more to the friendship than I wrote. I didn't think it would help to add why I feel the way I do, other than just saying that I do care about her feelings. We do confide in each other, we have nice lunches and we've had fun together separate from work. Most of our time together is mixed between talking about work and as we're working, talking about our personal lives as well.
posted by mitzyjalapeno at 9:33 AM on January 6, 2008

Best answer: quit. If she were really your friend, she would treat you so much better.

I can give a ton of reasons as to why you should, but I will just stick to one - Life is too short to spend it working in a job that is killing you.

Some companies will suck the life out of you if they know they can. They find a person who will work hard, aim to please and be loyal (as well as be susceptible to guilt trips). When they find a person like this, they exploit them to death. They pay them badly and then they give a bonus once in a while to suck em back in.

This company is like a bad boyfriend or girlfriend who treats you terribly most of the time, but you are so loyal to them, because you want to prove to them that you are worth it. Then once in a while, they do something nice for you, and you think - wow, it was all worth it!

Trust me - I have worked for a company such as this (and I have had girlfriends such as this, and I know of women with boyfriends such as this) - and leaving is the best thing you can do.

And before you say "But I am grateful for all the experience I learned" or "They were the only ones to give me a chance" or something like that, stop! Yes, you are grateful, but it doesn't mean you have to be a doormat. Trust me, if you weren't good at what you are doing, you would be out the door! You are grateful. That is good. But you showed your graciousness already. Now you are even. They gave you a chance. They allowed you to gain experience. You stayed there for five years. You are EVEN.

What has your boss done for you other than give you a few bonuses and a few days off here and there? What good is that when the majority of your time, you are being taken advantage of?

If it helps, don't look at it is "quitting" - you are not a quitter - but you must be an investor - invest in yourself! Move on for youself! Take care of yourself! Be good to yourself!

Finally, I should add that you are not nuts. I know of quite a few people in situations similar to yours. I have witnessed people staying in caustic environments out of loyalty to the company. But now, you have to be loyal to yourself. And of those people, the ones who have moved on are so much happier where they are.

Your job is like a bad boyfriend - DTMFA!

Good luck!
posted by bitteroldman at 9:57 AM on January 6, 2008 [15 favorites]

If she's really your friend, then she ought to be happy for you that you've found a job making twice as much with benefits... especially since you have children to provide for.

But none of the actions you've described make it sound like she's actually concerned about you or your family's welfare. If she's more upset about losing her servant than the quality of your life, then it seems like you're far better off without her.
posted by Gianna at 10:15 AM on January 6, 2008 [1 favorite]

occhiblu is saying some very astute things about the tendency women have to confuse friendship and business relationships. I would add to that the observation that it's certainly possible to have a relationship that combines both; but if she were really your friend, she would have treated you a hell of a lot better than she did.

She depended on you to run her business, yet she relentlessly micromanaged you and grossly undercompensated you. She paid you peanuts, and in return she got 24/7 remedial hand-holding in basic business skills -- as well as a full-time therapist, security blanket, and punching bag.

Read your own post! Of course she's unhappy you're leaving! She exploited you mercilessly -- and you went along with it.

You're like the girlfriend who always puts out and keeps the house spotless -- then wonders why her abusive, neglectful boyfriend gets so upset when she tries to leave.

You should take a serious look at concept of boundaries, and where else in your life you are letting other people manipulate and exploit and invade you.

Good for you for leaving! Keep walking. Don't look back. And don't worry about salvaging the friendship, because you don't actually have one now.
posted by ottereroticist at 10:30 AM on January 6, 2008 [1 favorite]

Am I just being manipulated into coming back?

If you have to wonder if you're being manipulated, you are.

nthing what everyone else upthread said so eloquently.

This is a shitty situation.

This woman is taking advantage of you. I'd wager that she doesn't think of you as a separate human being, but more as an extension of herself.

A little bit about friendship: friends respect your personal time and personal space. They're not calling you ten minutes after the alarm goes off with a whole bunch of demands. When they call you on Christmas Day, it's to wish you a happy holiday.

I've looked into some other jobs, and I've been offered nearly double what I was making with full benefits and a third of the workload.

RUN! Don't walk. RUN! RUN to that new opportunity. Be selfish. Be cold. Be Not Nice. In the business world, no one is looking out for you but yourself. Take the opportunities that you're given.
posted by jason's_planet at 10:53 AM on January 6, 2008 [1 favorite]

It's been said better above, but definitely get out of there. Take double the pay and use it for your family and yourself.

No job is worth more than the pay. None. If she burns the friendship because an underpaid employee left, she's not worth it.
posted by ®@ at 11:07 AM on January 6, 2008

Best answer: added thought... one of these two things is true:

She thinks she is paying you a fare wage. If this is true, she will have no trouble replacing you.

She knows she is not paying you a fare wage. If this is true, she is using your good will to save money, and is not a good friend.

Either way, you should take the higher-paying job.
posted by ®@ at 11:19 AM on January 6, 2008

I have been friends with all my bosses (I've been really lucky). It was never like this, whether they were men or women. When I've left or thought of leaving every company I've been at, my bosses' reactions have always been to ask what they could do for me to stay, to understand when it wasn't going to work out, and to give me awesome recommendations. That's how it should be if they're really your friend.
posted by nev at 2:09 PM on January 6, 2008

Congratulations for leaving and for asking for advice. Basically, you have been in a co-dependent abusive relationship. I've been in similar situations. You've gone part way but not all the way. I suspect you know that continued friendship with her is impossible, but you need time and support and resolve to make the break.

There is no way for the friendship to continue or to end well. Waste of time to try and make her accept your decision and give you approval. Resign yourself to that. Write out what you have told us, go into lots of detail and give her that letter.

It will be much easier if you tell her in the letter that you cannot be friends and cannot be in communication with her any longer. I know this sounds harsh, but the kind of friendship you need would require her to behave very differently, so differently that you would be making excessive and specific demands and requirements. Really, if you have to set a lot of limits in a friendship in order to tolerate it, then you are trying too hard.

It is possible to care about someone and still end the friendship. Don't let her guilt-trip you into thinking that ending the friendship proves a lack of feeling on your part.

You will feel lots of guilt and ambivalence and self-doubts. You will need good support from friends, family and professionals (without it you will be far more miserable). This will be a very big emotional event in your life and will last for months if not years. The silver lining is that you have a chance to understand and change some attitudes and behavior patterns of yours which do you no good. Embrace the challenge.
posted by conrad53 at 2:49 PM on January 6, 2008 [3 favorites]

Not exactly taming the shrew, it's more like tolerating her.

The very title of your question belies your description of her as a friend.

Friends are people whose company you enjoy, whom you actively seek out.

You don't tolerate your friends. You like them. You love them.

"To tolerate" is the kind of verb you'd use to describe your relationship with a goofy neighbor or a coworker with dodgy personal hygiene.
posted by jason's_planet at 3:14 PM on January 6, 2008 [1 favorite]

Congratulations for leaving and for asking for advice. Basically, you have been in a co-dependent abusive relationship.

What a very lucid and helpful response. conrad53, whatever nightmares you've lived through were not wasted if you learned stuff like this. Favorited for referencing in the many threads that boil down to this same scenario.
posted by ottereroticist at 3:28 PM on January 6, 2008

Best answer: The OP said:
"How can I express to her that I need to move on, but that I still want everything but the best for her? I've tried, but it doesn't seem like she believes me. Am I just being manipulated into coming back?"

You sound like you're in a really difficult situation. But I think you want something that you can't have - for her to be okay with the fact that you are leaving and for her to be supportive of you as you make this transition. The way you've asked the question implies that you think there is some 'right' way to phrase what you are trying to tell her. Because her response would be more positive if you found those words, instead of the ones you're using.

She's going to feel how she's going to feel. You sound like you approached her with good intentions (regardless of how 'well' you explained yourself), and she is choosing not to recognize the sincerity and honesty you are offering her as a friend. There's nothing to be done about that, sadly.

The fact is the transition is hard for her, but it's often hard, hard, hard on both employees and bosses when a valued employee leaves (for different reasons). Lots of wondering how to find the time/energy to train a new person, few people rush into uncertainty or drastic change if they can avoid it. Perhaps she wishes she was handling this better, but she's not.

The one piece of advice is this: She may not know what she is going to do in your absence, and it ISN'T YOUR JOB to figure that out for her - she is the boss - and it's her job. It's why she makes more money than you.

But a friend would set boundaries and give support. For example, not to engage her in work related questions after say, a month after you stop working. Also, when she comes to you with a work related problem, (can't find a new staff person yet *there are temp agencies*, etc.) tell her "I realize this is a difficult time for you, but you are an intelligent, capable woman - you can find solutions for your business."

Congrats on taking the next step in your career!
posted by anitanita at 4:59 PM on January 6, 2008 [2 favorites]

How can I express to her that I need to move on, but that I still want everything but the best for her?

That expresses your sentiments perfectly and succinctly, those very words. Very well done. Say that, then move on.
posted by Robert Angelo at 6:55 PM on January 6, 2008

Response by poster: Robert Angelo, you took my freudian slip and made it work - thanks. Thanks to everyone. The comments have been really helpful. I have been confused on my priorities, and now it's hard for me to adjust to my supposedly "selfish" priorities being at the top. It's good to know that I'm not the only one to go through this type of situation.
posted by mitzyjalapeno at 8:35 PM on January 6, 2008

I've had a few friendly bosses, but from my experience, only the true friends would truly understand when you need to GTFO and get a better job. Of course they'll be upset that you're leaving, but they understand that there are better things out there.
posted by booticon at 8:40 AM on January 7, 2008

(I know I'm kinda late to answer, but I figured I'd just chime in with that seeing as you've gotten so many eloquent responses already.)
posted by booticon at 8:41 AM on January 7, 2008

from anitanita: Also, when she comes to you with a work related problem, (can't find a new staff person yet *there are temp agencies*, etc.) tell her "I realize this is a difficult time for you, but you are an intelligent, capable woman - you can find solutions for your business."

This is a GREAT point! Even after you get out, she will probably try to suck to back in! Beware the undertow that is your guilt-tripping ex-boss! She will continue to call you if you let her, and then you will be giving her advice for FREE.

You seem to be a nice, considerate person, so I won't say not to help her out at all, but DON"T go into the office anymore, be 100% aware of her habits (i.e. is she calling more and more frequently or asking bigger and bigger favours), and eventually cut off any work-related conversation (even if that means cutting off the entire friendship) - Like anitanita said, a month is good (not a day more!)
posted by bitteroldman at 2:58 PM on January 7, 2008 [1 favorite]

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