Dear Friend or Foe,
My friend, "Sally," is constantly bugging me about going into business with her. But I know that doing so would be a disaster! In the five years of our friendship, Sally hasn't held onto a job for longer than six months. She constantly picks fights with her employers, fellow employees, and peers, and has a huge chip on her shoulder that keeps her from realizing that most of her work troubles are a direct result of her own actions. Up until now, I've deflected her requests with excuses, and they’ve all been valid. (I work full-time already and am not ready to take on another major commitment.) But she just keeps bringing up new ideas again and again.
Do I continue to gently turn her down, or do I need to be honest with her and tell her that there's no chance in hell I’ll ever participate in a business venture with her? I tend to be a forthright (though diplomatic) person and am known for speaking my mind. Doing so in this case might make me feel better and might get her to stop asking, but it would absolutely destroy our friendship. Do I just suck it up and keep saying no? Or is there a better solution that would make her stop pestering me while preserving our friendship?
Tired of Saying No
It seems to me that, in today’s confessional culture, people are too convinced that others need to hear the truth. In this case, what would it accomplish—other than making Sally that much more defensive and insecure? Besides, by a certain age, our personalities are mostly set in stone. We can tweak our behavior here and there, but telling someone what’s wrong with him or her is, generally speaking, a waste of time (that’s also destined to complicate your own life).
Although you describe Sally as bellicose and insecure, it sounds as if, for whatever reasons, you’re determined to try to maintain your friendship with the woman. So if you know she’ll be mortally offended to hear your real reasons for not wanting to go into business with her (and who wouldn’t be mortally offended to hear that her friend considers her a bullying shrew?!), I suggest resorting to a white lie. Tell Sally that, on principle, you don’t think it’s a good idea for old friends to go into business together—and you’ll never be convinced otherwise. Other friends of yours have tried the same and lived to regret it, as laughter and camaraderie have quickly deteriorated into endless fights about money. With any luck, this should permanently put Sally off the notion while also preserving your friendship.
Friend or Foe
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