Why Trying To Impress People Never Works (…And What To Do Instead!)

bold authenticity not nice omos self-esteem May 01, 2022

Do you constantly find yourself secretly wanting to impress people? 

Whether at work, home, or out, are you always desperate for people to see you as successful, funny, smart, sexy, skilled, cool, or special?

Do you spend all of your social time trying to prove that you’re worthy of other people’s attention?

While this may often be unintended, it is a tendency to which we’re all susceptible. 

Alas, it’s an unwinnable game.

Today, we’re going to discuss why attempting to forcefully win people over is a losing strategy and what you can do instead to show yourself in your best light without sacrificing your confidence.

So, let’s begin with breaking down the strategy of trying to impress people.

When trying to impress people, there are simply too many unknowns.

Let’s say that you want to impress someone—we’ll call him Joe.

First of all, you have to know what impresses Joe (whether you want to admit it or not, this is a very difficult thing to know). Ignoring that fact, you have learned that Joe is into art, so you try to impress Joe by telling him all about a piece of expensive artwork that you recently purchased.

Now, this might be a winning strategy but it’s just as likely to push Joe away.

What if he doesn’t like that kind of artwork?

What if he asks you about it and you can’t talk intelligently about why you like it?

What if he only likes velvet paintings of dogs in clown suits?

This isn’t the only thing that could go wrong, either. Joe might not like people who brag about art purchases. Joe might feel resentful that he can’t earn that much with his own art. Joe might feel envious or threatened by your financial success.

The problem with trying to impress people is that you cannot know, without a shadow of a doubt, what will or will not impress them.

Not only is it impossible to know what might impress someone, it is also impossible to know if trying to impress that person will yield the result you want.

Let’s go back to the conversation with Joe. What are you focused on during that conversation? Are you focused on Joe and how he feels? NO! You’re focused on how he’s looking at you and what that might mean; you’re focused on every little micro-gesture; you’re focused on whether or not Joe is impressed with you.

Unfortunately, if you feel that Joe isn’t impressed with you, the game is over and you feel dejected and hopeless. You feel like a loser.

This is not an effective way to relate to people and connect on a meaningful level.

Think about it. Let’s say you beat the odds and get exactly what you want: Joe is impressed. Yay! You won!

Did you win, though?

In truth, beside missing out on the joy of a truly delightful conversation in which you can share your authentic self, you have now set yourself up for a relationship built permanently on desperation and game-playing.

To begin with, whenever you talk to Joe from now on, you had better be ready to engage in an engrossing art conversation. So, study up!

What’s worse, though, is that you’ll always be wondering if he likes you; you’ll always be anxious that he might think you’re a fraud; you’ll always be worried about sustaining that façade; you’ll always question whether you’re good enough.

We don’t try to impress people because we’re confident in our self-worth—we do it because we want people to like us or hire us or respect us. We do it because we are insecure.

 So, what is the antidote to this all-too-tempting social strategy?

Well, for anyone who wants to dive into social confidence training head-first, I’d suggest checking out my Social Mastery course in my comprehensive program, Confidence University. This online program is all-inclusive and offers you an opportunity to begin your intensive confidence transformation with guidance and support from the comfort of your home.

In the meantime, though, you will find it quite difficult to let go of trying to impress people without having another habit in place to guide you.

What is it that will make someone want to connect with you on a meaningful level? 


Listening and authenticity.


If you really want to engage people in a way that brings them back for more, then you’re going to have to be real with them—you’re going to have to be genuinely interested in what they say while also being willing to share something about yourself.

Often, we hold back from engaging this honestly because we’re afraid of how we’ll be judged if we show our true selves.

We worry that they might not think we’re interesting or cool or good enough in some way.

Here’s the thing, though: if we never put ourselves out there, then we’ll never find the connections that we seek. And that legitimate connection from one person to another—whether romantic or platonic—is more satisfying and nourishing than any false connection based on game-playing.

In fact, that honest connection is so significant that it’s worth risking your discomfort to achieve it.

Think of it this way: you finally meet Joe and he’s not impressed with you . . . but then you also fail to make a connection with him as a friend. Is that the end of the world? Maybe you didn’t make a new best friend, but consider the alternative. Would you rather play the “impress you” game, fake your way through the relationship, and always worry that it will fall apart? Would you rather always feel anxious and desperate around Joe and everyone he knows?

On the other hand, wouldn’t it feel better to be your authentic self and attract the people who are most resonant with you? Wouldn’t if feel better to be around people who actually want to spend time with you? Wouldn’t it feel better to talk about things you really like and relax into a joyful and authentic connection?

I can’t answer these questions for you. All I can do is offer my own experience.

I tried playing the “impress you” game for years, and it never once resulted in a relationship that advanced my life in any quantifiable way or even made me feel good. Now, I spend my energy fostering relationships that make me feel comfortable in my own skin . . . and I’ve never been happier.

The choice is yours.

As always, I ask that you please share your questions and comments below! What are the “games” you play to try to win people’s attention? What could you do in conversations to reveal a bit more of your authentic self? What helps you connect to new people meaningfully in conversation? Please share your experiences with one another through this community so that we can continue to learn and grow together! 

Until we speak again, may you have the courage to be who you are and to know on a deep level that you’re awesome.

Reading blogs and watching videos online is a start...

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