PC: https://www.flickr.com/photos/thriftylook/9675591155

Recently, I sat down for coffee with someone, and we had a really good talk about philosophy, investing and everything in between. While that sounds high-class and fancy, it really wasn’t. We were inside a McDonald’s. McDonalds — the land of greasy food and loud, greasy, crying children.

So as I’m eating my Fillet O Fish, and he’s scarfing down some pancakes, it comes up how we are both very introverted people. Isn’t that weird? Two introverts decide to meet for coffee and… talk?

I mean, we’re always told that an introvert is someone who becomes drained by being with other people. That an introvert doesn’t like talking to strangers. That an introvert would much rather be at home reading books.

So since what I was doing (talking to a stranger in a loud location without books) flew right in the face of being introverted, I had a really proud moment! In my mind it went something like:


I can safely say that this wasn’t always the case.

One of my most vivid elementary school memories was being a completely awkward, social loner. I was sort of chubby and never really liked to play sports either. Since I hated being trash at soccer and basketball, what I would do to sort of “fit in” and be socially accepted was be a coathanger.

Prime business season was when it was spring, the sun was coming out, and all these kids started to get sweaty with their coats on. But coats should never be left on the ground, right? So every time someone needed to take their coat off, I would grab it for them, hang them on my arms, and go run around looking for someone else who needed the services of the coathanger. I took pride in my ability to hold ten coats at once, and always find and return them when recess ended.

They say societies have defined roles. Some have the hunters. The cooks. The healers. I was the coathanger.


That social awkwardness followed me all the way until around Grade 9. I would excuse myself from long conversations. Be intimidated and suspicious of any stranger who wanted to talk to me. Aha, if a girl decided to talk to me that meant she likkeedddd me.


But here’s the thing. Even in Grade 9, I knew that I was really interested in the field of business. Another thing that I knew in Grade 9 was that in business, I would have to talk to a lot of people and make those connections.

So this has actually been one of my little secret personal development goals through high school. If I couldn’t learn how to be good with people, then I might as well go into computer science. There’s less of a need to talk to people when you’re coding.

In my mind, there were a few key lessons that I learned along the way, that really helped me get better at the art of talking to people and being more “social”. These include my need to read up, the art of asking questions, lots of online chatting, and just forcing myself into social situations.

Reading About Talking to People

This is probably hands down, the nerdiest possibly way to learn how to be better with people, but I found it important for a few reasons. I always wanted to understand what is it that amkes people tick? What are some of the best tips and tricks that I can use in order to connect with people and make friends?

The fact that I felt that I needed to read a book speaks volumes about how introverted I am and how much I struggle with all of this, but I think that is actually a blessing in disguise. Having to work so much harder than your everyday extrovert, understanding some basic human psychology, and constantly thinking about how to interact with people has helped me get to a level of confidence and where I am today.

So what are the books? The ones that had the most impact on me were “Never Eat Alone” by Keith Ferrazzi and “How to Win Friends and Influence People” by Dale Carnegie. They both teach a lot of small and practical lessons that helped me get through a standard conversation and leave a good impression.

Here are some of my favorite lessons from these books! If they’re super obvious to you already, then congrats, you are better at talking to people than I am.

  1. Be Vulnerable: Are you having a bad day? Do you have some worries or concerns? Sharing those makes people trust you, and usually leads to them opening up too. After a few minutes of looking deep into each other’s eyes and confessing your soul, I’ve found that I can walk away having made a new friend
  2. Body Language: This is one of the most common and obvious ones, but there are some interesting subconscious tricks that I picked up. The oft-repeated one is “NEVER CROSS YOUR ARMS”, and always stay open. One of my favorites is that when someone is talking to you (or you to them), then lean forward! It shows interest. Hands down, the most interesting one is being a copycat. If you mirror their actions, people apparently seem to take a liking to you! If they’re doing a hand gesture or something, copy it when you talk! The easiest way to do this is actually just repeat something that they just said right back to them. “I like potatoes”…”Huh… so you like potatoes… that’s super cool man”
  3. Show Genuine Interest: Make someone feel special! If they’re talking don’t let your eyes just glaze over. Find a common interest, ask questions, sympathize, at the very least look really serious and nod you head. Show some interest and it goes a long way. If you find yourself falling asleep, then just change the topic of the conversation (or just politely walk away)

Asking Good Questions

The magical thing about learning how to ask good questions is that the total time you spend talking ends up decreasing significantly. A question takes 30 seconds. The answer takes 3 minutes. That’s a pretty good 1: 6 ratio, and my secret to getting through those conversations. Just let the other person talk 🙂

Asking good questions is just a matter of listening very closely to what the other person is saying. I like to think of it as chaining words and ideas together. Are they talking about how they love art? Ask them why? Is it because they enjoy expression and creativity? What’s their favorite medium? Why? How do they deal with a lack of creativity like writer’s block? Hmm writing, books, hey do you have a favorite book? Ew that author is nasty, why do you like him?

The word “why” is my new best friend.

Lots of Online Chatting

Talking to people in person doesn’t really give me enough time to think or get better. It’s sort of like practicing for a sport right? You never start sprinting or going all out right away, you have to start with the basics, or else you’re going to get screwed over later.

So what I did was a lot of chatting on Facebook messenger with friends and people that I had just met. Online chat gave me a few seconds to think of a good response, and practice keeping a conversation going. You do it a few times, start seeing patterns with what works, and what gets your r-bombed, and you just take whatever you learned and apply it to real life conversation.

Where I learned my craft

Forcing Myself Into Social Situations

There is no better way to get better at something than just going out and doing it. So that meant forcing myself to go to all these get togethers, events, and just putting myself in a situation where I had to talk to people.

Some examples are

  1. Post competition lifeguard party
  2. Pitch competitions
  3. Get together with a bunch of jocks. Jocks? I am definitely not a jock, and prefer reading, but I had loads of fun
  4. Local community and cultural showcases
  5. Talent show both with and without talent

For me it was just a matter of making sure that I left with at least one good conversation before I left. On good days, that takes like 10 minutes max. On the bad days, after lots of stuttering, weird looks, and polite excuses to run away from me, it never happens.

I have lost track of all the super awkward conversations that I’ve had over the past few years. The worst one involved someone I worked with at the pool before, and went something like:

“Hey ____, what are you doing here?”
“I go to university here…”



“I gotta go! BYE!”

What can I say? It’s a process.

If you’re an introvert, I hope you identified with a few of my struggles and picked something up along the way. Extrovert? Please teach me how to be better with people, I still need help.

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