I remember a time a while back when my counselor rated me as a high "people-pleaser." He informed me that this was something I need to work on, in the same excessively ginger tone you might use when telling a criminally insane friend that maybe hitting folks with tire irons is not the best way to win friends and influence people. My natural reaction to this was, of course, immediately to become extremely defensive. Sure, I'm a people pleaser, I thought. And good for me! And good for people, too! (Not that I actually said any of this out loud to him - wouldn't want to upset him by disagreeing!) People are pleased, and the people pleasers are pleased as a result - everybody's freakin' pleased! I thought that it would maybe be a good idea to launch a nation-wide organization of people pleasers and take our complaints to Washington!
I thought a whole big crowd would show up, but instead I got an enormous beige pile of beans.
Or perhaps not. At any rate, I understand perfectly well how people-pleasing can be bad - when it becomes turning the opinions of others into an idol. (See John 12:43) But on the other hand, this whole idea of "assertiveness" as healthy seems to run afoul of Jesus's admonition to turn the other cheek - to "not resist an evil person" (Matthew 5). Maybe the problem with people pleasers isn't that we let people walk all over us, it's that we whine so much afterward. I don't know. What do you think?