I recently found some notes from several years ago in a coaching program I was taking at the time. I had scribbled down a conversation between myself, and, my self. It was down and dirty and a lot of expletives were thrown around as I battled a bad people-pleasing issue I had going on. My favorite part of the exercise was:
Me: “So, basically, you’ve wasted years of your life, doing what everyone else thinks you should do and now you can’t make a fucking decision about anything without seeking someone else’s input on what you should do! That’s fucking lame!”
Me 2: “I see your point.”
Me: “Stop trying to please ME of all people! You know you’re pissed at what I just said.”
I know, it’s a nice fantasy that we can make everyone we work with, everyone we are friends with, and everyone we are family with, be happy 100% of the time.

Now, bring this habit into running a business, or being a leader, and it’s a recipe for complete disaster. I’ve learned the hard way, that when you lead a group, it is just not possible to please every one, every time. (I did try really hard, though!) That trying got me really tired, and it used up too much of my time.

When you run a business, people-pleasing can kill your profit. This habit is what will have you lowering your rates because you buy into sob stories, or because you want so badly to be liked that you start the relationship right off with anything you can do to make someone like you. Now, you’ve set a precedent – when someone comes back to do business with you, they will want more price cuts from you because you have trained them to devalue your service, which, in turn, will have you devaluing your service too, and, possibly, yourself – don’t do it!
Sometimes, you have to say no to what you don’t want in order to allow the space for what you do want.
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