How to Break Out of Your Shy-Shell


“You will become way less concerned with what other people think of you when you realize how seldom they do.”

– David Foster Wallace,
Infinite Jest

 

 

I could recall a particular memory of being 7 years old in primary school. I was in English class, and the teacher asked for volunteers to stand in front of everyone and talk about their pets. I remember one of my friends bravely volunteering himself and sharing a completely made-up B.S. story about having a pet parrot.

There were no volunteers after that, so the teacher started picking names. Out of sheer bad luck, I was called up. I was deathly afraid, so instead of doing as I was told, I cowered under my desk while my teacher and classmates nudged me to give it a shot. I stayed down there for a while.

As I grew older, my shyness gradually got to a more manageable level. But especially after Covid hit, I regressed a lot to that terrified 7 year old.

It affected me to the extent that even going to a restaurant or a café alone would cause my stomach to turn, and I would have to mentally rehearse going inside and making my order to calm my nerves.

But some time last year, I decided that things had to change. I was attending a talk by Red Hong Yi, a local artist that I admired, who was promoting her new book. I wasn’t normally one to attend social events, but this one genuinely caught my interest, because, Red Hong Yi. 

Before and during the event, I was a nervous wreck. I felt nauseous, and it seemed to me that anybody could probably notice how self-conscious and uncomfortable I was to be in a social setting that was filled with strangers.

When I got myself to approach Red Hong Yi for an autograph after the event, I was shaking. My mind was so preoccupied about the things I wanted to say to her, and trying hard to stop my shaking. And by the time I got back to my car shortly after that, I had already forgotten everything she said in our small conversation.

I remember getting a cup of coffee after that and parking my car at my favorite spot in my old neighborhood, where I liked to be with myself. Replaying the event in my mind, I thought, “Is this really how shy I am?”

Right there and then, I resolved to improve my social skills, and I came up with a rough plan.

I learned a lot of things along the way, which I’ll be sharing in this article, so that you could break out of your shy-shell too.

However, I do want you to understand that it’s a never-ending process of improving yourself. Because on some level, you will always feel a sense of shyness or awkwardness when you talk to new people. But over time, it gets more doable to simply acknowledge those feelings and go about it anyway.

So, let’s get started.

 

 

1. Do Whatever You Need to Feel More Presentable. I hate to break it to you, but appearances do matter. In an ideal world, the popular saying, “Don’t judge a book by its cover” would make a lot of sense. But the reality is, nobody has all the time and energy in the world to not judge us by our appearances. But more importantly, how we present ourselves affects how we feel about ourselves too.

I used to have a habit of growing my hair long. It wasn’t so much that I liked having long hair (in fact, it was quite annoying). But I grew it out anyway, just because I was lazy to get frequent haircuts. Yet, I felt like a hobo in my long hair, and this actually made me less willing to socialize with other people. So, I finally started taking to heart the endless feedback from friends and family suggesting that I look more approachable with my hair cut neat and short. And really, I started to feel more approachable, too.

There has to be a balance between being comfortably yourself and looking good to other people. Being more presentable doesn’t have to mean sacrificing who you are to be someone you’re not. It’s simply about being a better version of who you already are.

Going out in your jammies may feel nice, but you can be sure that other people are roasting you in their heads. So, find ways to make you both look good and feel good. Say, if you don’t feel like wearing flannel shirts, wear something else that’s nice and makes you comfortable. If you’re a guy and you decide that you do feel comfortable having long hair, at least — for the love of God — put in the work to keep it looking neat. 

 

 

2. Make the Process Fun. If you’re going to get through this, it’s not going to work if it feels like a chore that you’re forced to do. It’s going to be just a matter of time for you to get lazy and regress to your old ways.

To make the process feel a lot more natural to you, and fun, try putting yourself in social settings that are already aligned with your interests. This way, you’re not only challenging your social skills. You’re also opening yourself up to amazing, unforgettable experiences. Here are some of my own examples.

I love books, and I actually had fun attending Red Hong Yi’s talk. So, I started attending more author events, where I’d challenge myself to raise my hand and ask questions, and approach the author later for an autograph. And of course, in any given author event, I also get to learn plenty of interesting things about the author and their work. 

I also love coffee, and I go to a café at least once a week. So, I’d challenge myself to have small talk with the barista. Imaginary bonus points if the barista were attractive.

And of course, I love music. So, when one of my guitar heroes, Steve Vai announced a show with a meet-and-greet program, I jumped on the opportunity. For me, this was like a “boss fight” of the figurative game of improving my social skills. Because I knew I’d get super-starstruck. It was more than I’d typically pay for a concert too, but it was still a lot more affordable than what popular artists would normally charge for something similar. 

Besides successfully challenging myself to ask Steve a question, it was also one of the coolest and most valuable experiences I’ve ever had in my life. I can die happily knowing that Steve Vai gave me personal advice on creativity.

 

 

3. Be Curious. Talking to people becomes a lot more fun when you make the other person the star of the show, rather than yourself. By this, I mean being genuinely curious about who the other person is, what they do, what they like and what they don’t like — essentially trying to understand what life is like from their perspective.

At least for me, this is the real thrill in socializing. Everyone has their own story, and it’s always exciting to know how it goes. And you never really run out of things to talk about either, because there’s never an end to what you can learn about another person.

But there’s also another component to this. When you demonstrate this kind of interest in another person, they can easily warm up to you. The conversation becomes more lively, because everyone loves to talk about themselves. 

Not only that, coming from this place of curiosity naturally eases your anxiety and nervousness as well. When you’re more interested in the other person, you’re not as concerned about “selling yourself”, or saying the perfect thing, or making yourself look smart.

From my experience, this works great in formal settings too. Job interviews, for example, become much less daunting and much more engaging when you’ve done thorough research on the company and you sincerely resonate with what the company does and the values that they stand behind.  

 

 

4. Embarrass Yourself. At the core of being shy is the deep-rooted fear of being judged or criticized. Sometimes when I think of my 7 year old self cowering under his desk, I wonder what he was so afraid of. I realize, they were the same things that I’m still very much afraid of today: being laughed at, being told that I’m not good, that my ideas are dumb. It’s the same fear that all of us have always had. And it’s what we all wrestle with to our graves. 

But we have to understand one immutable fact of life, and that is, we all screw up. All the time. We’re always saying and doing silly things. We’re always falling short of what we really mean in what we say and do. And that’s fine. Because we’re only human. This is what real confidence is. It’s not in being absolutely sure of the prospect of success. It’s in being okay with the prospect of failure, and going through with it anyway. 

There’s another immutable fact of life that’s key here: no one cares about us as much as we think. In psychology, this is called “the spotlight effect”: we tend to believe that we’re being noticed more than we actually are. At first glance, this might seem depressing. But it’s truly liberating when you realize that no one cares about your shortcomings as much as you do.

Take inventory for a moment — you can easily think of the last time you embarrassed yourself, but not the last time that somebody else embarrassed themselves. So does it matter all that much to weather through a moment of embarrassment, or failure, or rejection? Probably not. Chances are, it will be forgotten in a while.

But still, getting yourself to socialize more can be really terrifying at first. Believe me, though, when I say it’s the toughest when you’re starting out. It can only get better as you keep doing it. Think of it as a form of exposure therapy. The more you talk to people, the more you get used to it, and the less you care about what others might think of you. 

We all have to start somewhere. Surely there are some short-term pain and discomfort in getting started and putting yourself out there. But they’re a bliss compared to the enduring pain and discomfort of staying the same and never having to challenge yourself. 

Get out there, dear reader. You got this.

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