How to Practice Disappointing People

It starts with this: Generally, people like you to fit the mental model they have for you.

Mental models make life easier for everyone. They make it easier to avoid thinking too much about every little thing that comes along. They allow us to simplify decision-making.

But we also use mental models to guide our relationships—so when you operate outside the model that someone has for you, it can cause distress or discomfort. Not only is it inconvenient (because you’ve disappointed them), but now they have to do the emotional labor of revising their model.

So in short, whenever you behave in a way that is unfamiliar to someone, it poses a risk of disappointment. 

You might think disappointing people only involves choices or behavior that directly affects them—but no! Weirdly, many people will be disappointed in your actions even when those actions have nothing to do with them. Crazy, but true.

This is key to properly understanding disappointment: it’s them, not you. But it’s also you.

Setting boundaries for yourself is a sure-fire way to generate disappointment from others. It will also elicit surprise at the realization that your life does not exist entirely to please people.

A few specific tips —

• Set realistic expectations: Clearly communicate your intentions, abilities, and limitations. No one likes this—they generally prefer for you to be able to do anything they ask at any time. Note that this is not a “set it once and forget it” type of action; it’s more like an ongoing process that sometimes requires revision as you go along.
• Be honest and assertive: Express your feelings, opinions, and needs openly and honestly, even if they may not align with what others want. (Bonus: when people ask what you think about something, tell them the truth instead of trying to figure out the answer they want to hear.)
• Learn to say no: not a tentative, halfhearted commitment, not “maybe,” not saying yes now and looking for an out later, but simply “no.” No is a complete sentence that does not require elaboration. Inevitably, however, saying no in many situations will cause disappointment.

It is often said that “trying to please all the people, all the time” is a recipe for failure. This is true, but rather than just trying to please “fewer people, some of the time,” perhaps you should focus most of all on trying to please yourself.

This too might disappoint some people. But guess what: in the end, they might also be impressed! Not everyone realizes it’s possible to go through life without worrying about disappointing others, so your positive example will be good for them.

Recognize that people’s disappointment often stems from their own unmet expectations or desires. By understanding this, you can better manage your reactions to their disappointment and focus on what truly matters to you.

Remember, practice makes perfect.

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