The Real Way to Boost Confidence

Sometimes I get interesting talking points from my clients. I think you’d find them interesting too, so here we go!

I can’t even boil this one down to a single client. It’s more like a recurring theme with a lot of my clients. It doesn’t matter if it’s with learning English, prepping for an interview, or asking someone out– everyone wants to know how to be more confident.

Whenever I hear about someone with confidence issues, it really hits home with me.

I, too, have had my fair share of relatable experiences with questionable self-esteem. And, I really think that if I could manage to get out of that kind of headspace, anyone should be able to do the same.

I can relate. I definitely empathize.

It’s also interesting when I do point out evidence to the contrary– things that the client should feel proud about– they’re often quick to dismiss it. Usually, it’s because they think I’m just being nice (I’m not– that kind of coddling is a waste of time) or they’ve really let their insecurities take over.

You can be insecure about anything.

Insecurities can stem from reasonable fears, but here’s the problem: we’re so good at convincing ourselves of their legitimacy. And when you’re good at making an argument to justify something, you can jump the gap from logical to illogical without even noticing.

Take snakes for example. I hate ’em. Can’t stand them. I’m terrified of them. There’s a sensical side to it: I don’t want to get bitten. I believe that’s a legitimate fear.

So then here’s the next thought in sequence: “I can’t go hiking. What if there’s snakes on the trail?” Still make sense. But if you don’t keep it in check, it can devolve into “What if I got to go the bathroom at night and a snake opens up the door?”

How do you keep your insecurities in check? Believe in yourself and spew a bunch of motivational quotes? Naw!

Well, I mean, you can… I just don’t think the effects will be long lasting. In the past, I’ve latched onto plenty of self-help books and empowering words– repeating phrases like mantras.

That kind of positive buzz can definitely feel good in the moment, but it’s not a real solution. It’s masking a deterrent with blind hope.

You can’t fight it with reason. The first “trick” is not to invest so much time in it.

Let’s apply this two another insecurity of mine: having a big nose.

[The Overly-Optimistic Approach]

Me: I have a big nose.

Positive Attack: No way! You have the most beautiful, not big nose… in the world!

Me: I think it’s still kind of big…

Positive Attack: You just need to love yourself, maaaan.

Me: But… I don’t love the fact that I feel like I have a big nose.

Positive Attack: You got to believe, maaaaan! #belieber


[The Less-Invested Approach]

Me: I have a big nose.

Accepted and Diverted Response: Sure. Maybe. I guess? Hey, does this affect how much you get paid?

Me: N-no… Why?

Accepted and Diverted Response: Cool… cool. Just checking. Oh you know what? We should get something to eat.

Me: You’re right. A big nose has no bearing on my actual day to day life. I can still live. I can still work. If I take care of myself, I can still find love and accomplish my dreams!

Accepted and Diverted Response: Did you say something? Sorry I wasn’t listening.


If you let things get out of hand, you can become insecure about anything and everything. And besides, your insecurity is always someone’s fetish out there. It’s true–there’s something/someone for everybody!

People want the story of grandeur. 

I know what you’re thinking. That “eh, whatever” approach sounds lame, huh. I think that’s also part of the problem why problems can grow into something bigger than they are.

People have the expectation of “fighting the good fight”. It might be subconscious, but the notion of “giving it your all” to overcome an obstacle just feels like the way to go.

Acknowledging your insecurities and focusing on something else? That doesn’t seem very epic. People are set on this idea of elimination: all or nothing. They want to get rid of it. They want the feeling of conquering your fears.

I’ll admit, my approach isn’t very sexy. And because of that, it doesn’t get too much praise. But here’s the second “trick” you need to know: even the most confident people have times where they doubt themselves.

You will have times where you doubt yourself.

Thinking otherwise? Well, you’re just trying to be a hip Instagram post I guess.

The real kicker is that the feeling of a lack of confidence might not ever go away. But how accurate of an assessment is it really?

I’ve done speeches where I felt nervous as hell, only to be told I looked so confident. And on the flipside, I’ve handled interviews very confidently, only to be perceived as a nervous wreck.

Who’s wrong and who’s right in those situations? Was confidence really the key?

Don’t get me wrong, confidence helps a lot. But if you idolize “confidence”, it’s no different than thinking money, good looks, or fame are the missing pieces to the puzzle of your success.

“I think everybody should get rich and famous and do everything they ever dreamed of so they can see that it’s not the answer.” – Jim Carrey

You don’t need confidence. You need to be able.

My good friend Sam once said something along the lines of “You don’t need to be a great person to be a good person.” In other words, you don’t have to set records and go down in history books to be a decent human being.

On the same token, you don’t have the be the most confident person to be confident. Instead of taking the confidence level to 11 and the insecurities to 0, just try not to spend as much time tuning into Big Insecurities 98.5 FM so often.

For my English-learning clients:

  • A confident person can still misunderstand the cashier.
  • You can have no confidence and still order your meal.

For my Public Speaking clients:

  • The people you interact with care more about what you can do for them than how confident you feel.
  • Focus on what you’re able to do for them: teach them something, save them money, or make them more money.

For my lovesick fools:

  • Confidence can be sexy, but insecurities are normal. A relationship of nothing but insecurities is neither sexy nor normal.

TL;DR Don’t dwell on insecurities. Don’t prioritize confidence. Do more shit, and the confidence will come on its own.

Published by Jon Dao

Formerly, the Conversation Coach

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