The Trap of People Pleasing

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Student: Professor, I need to confess something. I'm writing a paper on leadership, and the hardest part is admitting that I'm a people pleaser. I would rather swallow my real answer than risk hurting someone's feelings.

Professor: Then you have already done the hardest thing, which is to tell the truth about yourself. Most people would rather describe their virtues. But tell me, when you swallow your real answer, does it stay down?

Student: No. That's the worst part. I think of exactly what I should have said hours later, and then I'm upset with myself all evening.

Professor: Yes, the words always arrive after the guests have gone home. Is there a particular moment that troubles you?

Student: There's someone in my life who can be very pushy. I've done things for her out of kindness, but now it feels expected. I told her the following week would work better than Friday. Then she came to me and said she missed me Friday, that she had bought pizza, and she hoped she hadn't upset me. I reminded her I had told her I couldn't make it. Then she asked me something else, and I froze. I honestly can't remember the question. I just stared at her with wide eyes until she changed the subject.

Professor: And you think your silence was a failure of leadership.

Student: Isn't it?

Professor: It was a failure of preparation, which is a far more hopeful thing, because preparation can be learned. Notice that you did not lie to her. You did not say "Of course, I'm sorry, let's meet tomorrow." You simply had no words ready. A soldier who freezes in his first battle is not a coward; he is untrained.

Student: But why do I freeze in the first place?

Professor: I suspect because you are afraid of something. What is it you fear in that moment?

Student: That she'll be hurt. That she'll think less of me. That I'll be the bad guy.

Professor: Ah. Then the trouble is not really her pushiness at all. It is that you have handed her a key to a room that ought to belong only to God. Proverbs puts it plainly: "Fearing people is a dangerous trap, but trusting the LORD means safety." A trap, you see, is something that holds you in place. Which is exactly what you described.

Student: I never thought of freezing as being trapped. But that's what it feels like.

Professor: Paul felt the pull of it too, or he would not have needed to write, "Obviously, I'm not trying to win the approval of people, but of God. If pleasing people were my goal, I would not be Christ's servant." He knew a man cannot serve two judges. Every time you answer to her disappointment instead of to the truth, you have quietly changed courtrooms.

Student: But isn't it loving to protect her feelings?

Professor: That depends on what you are protecting. If you protect her feelings by hiding the truth, you are really protecting your own comfort and calling it kindness. Love is not the same as niceness. Niceness wants everyone to feel pleasant right now. Love wants what is actually good for them, even when it costs a moment of awkwardness. Scripture tells us to "speak the truth in love." Both halves matter. Truth without love is cruelty, but love without truth is only cowardice wearing its Sunday clothes.

Student: That stings a little.

Professor: Good medicine often does. Now, about your kindness becoming an expectation. What did you give her originally, and why?

Student: My time, mostly. Because I wanted to. I enjoyed it.

Professor: Then it was a gift. And a gift, by its very nature, must be free on both ends. Paul says, "You must each decide in your heart how much to give. And don't give reluctantly or in response to pressure. For God loves a person who gives cheerfully." Notice that giving under pressure is not what God asks of you. When a gift becomes a debt, it has stopped being a gift. You do her no favors by letting her believe otherwise.

Student: So how do I keep from freezing next time?

Professor: You prepare a few plain sentences in advance, the way a traveler keeps a few coins in his pocket for the toll. Something like, "Let me think about that and get back to you." Or simply, "That doesn't work for me this week." Our Lord was remarkably economical on this point: "Just say a simple, 'Yes, I will,' or 'No, I won't.'" You need not explain, defend, or apologize. A short answer is not a rude answer.

Student: And if I still freeze?

Professor: Then you pause, and you are not ashamed of the pause. James tells us to "be quick to listen, slow to speak." Slow to speak is a virtue, not a defect. The only real mistake would be to let the silence be the end of the matter.

Student: What do you mean?

Professor: You said the right words come to you later. Very well, then use them later. There is no law that a conversation must be finished in one sitting. You may go back to her and say, "I've been thinking about what you asked the other day, and I want to give you an honest answer." That is not weakness. That is courage taking the long way around, and it arrives just the same.

Student: I hadn't considered that going back was an option.

Professor: It is often the better option. The answer you give after prayer is usually wiser than the one you would have blurted out under pressure. Paul hoped our conversation would be "gracious and attractive so that you will have the right response for everyone." The right response, not the fastest one.

Student: So leadership isn't about never freezing. It's about where my security comes from.

Professor: Exactly so. The person who is secure in God's approval can afford to disappoint people. Not carelessly, but honestly. And here is the curious thing: those who stop trying to please everyone usually end up serving everyone far better. You will find you have much more to give once you are no longer giving out of fear.

Student: That gives me something to work toward.

Professor: Then begin small. Say one honest thing this week that you would normally swallow. Courage is like any muscle. It grows by being used, not by being admired.

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