How to be More Creative: The Obli Challenge - Part 2

How to be More Creative: The Obli Challenge - Part 2

Great ideas come from unexpected places.

This was my central thesis in Part 1 of the Obli Challenge.

With this premise, I expanded the content I consumed. I read articles that I normally wouldn’t have and I dug into the different sides of controversial issues.

But new ideas don’t only come from reading. When I reflected on how to build on the Obli Challenge, I realized there was an opportunity to expand my worldview by broadening the types of people I talk to.

Repeated studies have shown that diversity of thought drives better decisions, creativity, and innovation. A classic sociology study by Mark Garnovetter also demonstrated that most job opportunities don’t come from close friends, but through acquaintances – people you see occasionally or even rarely.

However, if you’re anything like me, the majority of your interactions are with the same people. I have a core group of friends that I hang out with and I seldom meet anyone new. Because I also tend to befriend people with similar backgrounds as me, the interactions I do have rarely provide fresh perspectives.

So what’s the solution?

I thought about joining a social group like a kickball league, but aside from hating all forms of physical activity, my experience with those groups is that you meet people who are similar to you. That’s when I stumbled across a Meetup called “Meetings Humans of New York”. On Saturday at 11AM, I joined a circle of strangers standing in front of the Barnes & Nobles in Union Square Park. After brief introductions, we broke into pairs to strike up conversations with people in the park.

The thought of approaching a stranger terrified me. But my more experienced partner, Edward, pointed to a person sitting on a bench and told me to talk to him. Not wanting to appear weak, I sat next to a man wearing knee high socks and a brown polo playing with his Samsung phone. After gathering my courage for a few seconds, I him whether the Farmer’s Market next to us was here every weekend. Before I knew it, the man was sharing his experiences from living in New York City for over 25 years.

I had more than one fascinating conversation that day. I’ve also been to the Meetup several more times and have even started approaching people on my own. Similar to Part 1 of the Obli Challenge, I can’t consciously tell if I’m more creative. However, I do believe I’ve become a better listener and more understanding of different viewpoints. While I’m still intimidated by approaching strangers, I’ve also developed tactics to handle that fear.

So what if you also want to break out of your comfort zone and meet new people? Even if you don’t have a Meetup near you, there are parks, coffee shops, and bars. Regardless of where you live, here are some tips and tricks:

1. Set aside dedicated time to talk to new people.

Think about your typical day. How many times did you think “I should talk to someone new”? My number is between -1 and 1.

We’re constantly absorbed in our own lives - we’re dealing with the latest problem at work or responding to our friend’s last text message. We don’t talk to new people because we aren’t actively trying to talk to new people.

By setting aside dedicated time to approach strangers - even if it’s just one hour a week - you make sure it becomes a priority. Even though I also approach people on my own, I continue to go to the meetup because the dedicated time holds me accountable.

2. Acknowledge your anxiety and treat each approach like an experiment.

I know people who are completely comfortable striking up a conversation with a stranger. I am not one of those people. Even after approaching dozens of people, I’m still anxious about going up to someone new. I’ve just developed some strategies to manage my emotions.

The first is to acknowledge that it’s natural to feel fear. Whether because of “stranger danger” conditioning as children, or because evolution has instilled a fear of social rejection in us, our default state is to feel apprehensive about meeting someone new. The key is to realize that just because you feel a certain emotion, it doesn’t need to dictate how you act.

The second is to reframe what you’re doing as an experiment. Each new person is an opportunity to try a different approach or persona. Focus less on the restless thoughts running through your head, and more on the challenge at hand. This also helps you bounce back when you get rejected because each rejection is a learning opportunity. Speaking of which…

3. Hold zero expectations for each person you approach.

Some conversations are captivating. I had an hour-long conversation with a retired military consultant named David about business and life.

For every meaningful conversation I had however, I had several more rejections. Whether because of my approach, timing, or other person’s state of mind, the person I tried to start a conversation with would not engage, and in some cases, would simply get up and leave.

By approaching each person with zero expectations and acknowledging that they may not want to talk for reasons outside your control, every rejection stings a little less. Some days you will engage with several people and some days it will feel like nobody wants to talk to you. Accepting this reality now makes those unfortunate days a little easier to bear.

4. Find a friend to go with you, but not a close friend.

I think part of why the meetup was successful was because we approached people in pairs. The extra person filled in conversation gaps and made going up to a stranger much less intimidating. If you can find someone to meet new people with you, you should do so.

However, just don’t find too close of a friend. It’s easy to just talk to your friend the entire time and forget your original purpose. Constantly remind yourself that your goal is to meet NEW people and if you find yourself talking to your friend about anything other than who to approach next, immediately switch back to the task at hand.

5. Be okay with a little discomfort in your conversation at first. Probe into the other person’s life.

When I first started approaching people, I thought the conversation would spontaneously flow. That’s not the case. Conversations among strangers are naturally uncomfortable and unless you’re talking to a great conversationalist, there will be lulls in the conversation.

Don’t immediately end the conversation when it gets awkward, try to keep it going. What works for me is to constantly probe into the other person’s life. People like talking about themselves and it’s more common to not delve deep enough into another person’s story than too deep.

Force yourself to be an active listener. When we aren’t listening, our body language gives us away, even when we think we’re faking it. If it feels like your attention is drifting, briefly focus on the sensations of different parts of your body – your toes, your legs, your hand - before reverting your full attention back to what the other person is saying.

How to approach people

This has its own section because I imagine it’s the most common question. Starting out, I looked for the one line that would get people to instantly open up to me. You will likely be disappointed with my response, but my best advice is to try different approaches and see what works for you.

I usually approach people with a question, even if I already know the answer. I’ll ask whether the “water park” in Union Square Park is open to the public (the answer is yes). From there, I’ll follow-up with additional questions and build on the other person’s answers.

A common approach I’ve observed from my partners is called “triangulation”. They will comment on a shared experience – the weather, the other person’s clothing, a book they’re reading, or even a street performer in front of them, to start the conversation.

Nima, the host of the Meetup group, will walk into an area, observe the body language of those around him (e.g. who looks up and makes eye contact) and sit next to someone who appears receptive. He waits 30 seconds before trying to start a conversation.

Another girl in the meetup introduces herself with “Hi, I’m Angela” and, without pausing, says “I’m going to tell you a little bit about myself and if you’re comfortable, you can tell me a little bit about yourself.”

Test different approaches and you’ll quickly discover what’s comfortable and natural. You’ll also find approaches that don’t work.

For a week, I tried “Hi, I’m trying to meet new people, do you have time to chat?” After getting several nervous looks and striking out every time, I stopped.



Part 2 of the Obli Challenge isn’t easy. It’s nerve-wracking to put yourself out there and approach a stranger. However, the sense of accomplishment you get from having a great conversation makes it worth it. I’ve learned about men’s fashion, street vendors, and beer. More importantly, I’ve gotten a glimpse of the personal stories behind each of these topics. I encourage you to go out there and discover some stories for yourself.

Other Articles You May Enjoy

How to be More Creative: The Obli Challenge - Part 1

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4 Tactics to Get Out of Going Out

How to Get Organized Through the 5S System

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Photo by Christopher Burns on Unsplash


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