How to be bold

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4 min read

Fortune favours the brave. Or at the very least, being bold lets you seize the initiative and swing things in your favour. Whatever it is, I know from experience that being a little bolder often results in something good.

Hannah Fry 1 explains in The Mathematics of Love about the Gale-Shapley matching algorithm that proves: “If you put yourself out there, start at the top of the list, and work your way down, you’ll always end up with the best possible person who’ll have you. If you sit around and wait for people to talk to you, you’ll end up with the least bad person who approaches you. Regardless of the type of relationship you’re after, it pays to take the initiative.”

Why we are shy

Our instincts protect us by making us afraid of things that endanger us. And as social animals, we fear being thrust into a situation that exposes us to people we are unfamiliar with in our social circle.

Fear of being made fun of. Fear of social engagement, especially with strangers. Fear of the unknown. We are not sure how others will react to us. Will they make fun of us or thing that we are weird?

As an introvert, I’m inclined not to interact with others.Despite being an introvert, I enjoy engaging others in conversations, even if it leaves me drained. I value discourse, both with people who share what I know, and others who challenge me to rethink my views.

Another reason to put myself out there is that as an entrepreneur, I need to be meeting new people to increase the chances of having opportunities for work or expanding my network. I find myself uncomfortable with making that first interaction that I know would open up myself to strike up a conversation.

I just need to push myself to step out of my comfort zone.

How to overcome shyness

When I walk my dog, I talk to other dog owners. Others are people who love dogs and want to greet the dog.

As an expat in China, I would approach foreigners I meet just to introduce myself as a fellow expat. I would also offer to add them to group chats for the expat community in our neighbourhood and district.

Attend events. It is easy to find events for your hobbies or interests in the modern era. Make the effort to go to these events so you meet like-minded people. When you have a common interest, you have more to share and talk about.

Be helpful. When you see someone who looks like they need help, offer assistance before they even ask for it. The most common example is if you see someone who looks like they are looking for directions. Offer to point them the right way before they even approach you.

I met my business partner because I engaged in conversation with people I encounter. You’ll be surprised what being bold can introduce to your life!

What to talk about

It doesn’t matter that much what you talk about. When you talk about people, they tend to be more willing to open up, especially when you ask open-ended questions.

When they see that you’re interested in what they have to say, it gets them to talk more about the topic.

Give honest compliments. It makes helps to warm them up to you and people are keen to talk about themselves. For example, I don’t hold back from telling them when I think they look good. I often think that doing so makes my day more than it makes theirs.

The weather is a good start when it is something bad, such as really scorching, sunny days or heavy rain. But you might want to avoid it if it might sound too much like you have nothing else to talk about.

Look for points of similarities so you can find topics to talk about.

Be bold

If you haven’t tried what I mentioned, I urge you to give it a go. You’ll be surprise how it might change your life. What’s the worse that could happen? Someone might ignore your approach and walk off? If they do, then they aren’t worth your time anyway.

Do you have any other ways to engage people? Have you had any life-changing experiences or bad ones from trying to talk to strangers? I’d love to hear about it.


  1. Via Farnam Street.