Writer, cartoonist and New York City transplant Nathan W. Pyle is the creator of the street-savvy, GIFed-out NYC Basic Tips and Etiquette. Lubna Batool, an 11^th-grade New Yorker, is a big admirer of his work, which gives newcomers to the city the little tips no one else will—like that one $20 umbrella will outlast four $5 umbrellas and that one should be wary of an empty subway car.

In the week before Pyle steps on the TEDYouth 2014 stage, we asked Batool to interview him. Here’s an edited transcript of their conversation. 

What is it about the subway and the sidewalks of New York City that you find interesting?

People. That’s the short answer: people are very interesting, and there are so many different kinds of people here. The excitement of New York is that you’re constantly surrounded by strangers. It challenges the way you think, because, even just overhearing conversations, you realize we all think very, very differently. I love that about New York. But one of the interesting things about the city is that we can all agree on a lot of these rules — about the way a line is supposed to work, or how an escalator should be walked on. We agree on these things even though we disagree on a lot too.

What do you do in your spare time?

I live in Manhattan and my girlfriend lives in Brooklyn, so I spend a lot of time on the subway. That’s where I do a lot of my best thinking. My best ideas come from just looking at other people and thinking about what to write.

What is the most difficult decision you had to make in the last two years?

My most difficult decision was whether or not to stop freelancing. For many New Yorkers, the question is: should I freelance or should I take a salary job? As a freelancer you have a lot more risk, but there’s more freedom. With a salary job you have stability, but it also means that you have to turn down a lot of opportunities. Freelancing is less attractive as you get a bit older because you start to think about maybe marrying someone or having a family. In my case, I ended up taking a salary job. I work for BuzzFeed full-time and I haven’t regretted that, because they treat their employees very well. Some companies don’t treat their employees well and some companies do.

What do you do at BuzzFeed?

I just published a quiz right before I got on the phone with you. A lot of people don’t understand that there are people who write these things — so I’m one of those people. Today it was about breakfast cereal, but then I also wrote a post about dogs. These are things that I can write about. I also write about my faith sometimes, or about advertising, or about philosophy.

One of the things I write about most is: What if I were born in a different country and I came to America — what would that be like? I did an exchange program in Kenya and, the people I lived with, they grew their own food. I learned that many people in the world are much closer to the source of their food. If I were from somewhere else, I would probably not be working on a computer as much because I might actually, say, tend to my own land.

Where would you like to be in your career five years from now?

I definitely want to write more books. I’ve written one so far — about the city. I might write a second that’s about church. I grew up in the Protestant Christian church, and there are a lot of awkward social interactions that happen at church. It would be nice for people to understand the kind of cultural phenomenon that happens. I came from a place in Ohio where a lot of people were accustomed to having churches on every corner. In New York, it’s a lot more multicultural and there are more religions represented. I am in that in-between ground where I can help people understand: here’s what pluralism looks like.

What made you want to work here in New York?

I really like the fact that, in New York, you’re competing against the best of the best. I think that’s what draws so many people here.

If you could travel to one place, where would you go?

I would love to go to Jerusalem. When I was in college, I studied Bible and Theology, so you read about all these places in Israel. It’s another example of where you get a first-hand look at people of many different religions in the same city. I would be very interested to see all of that.

Who is one person that inspires you?

People who think outside the box are some of the most interesting, like Frank Lloyd Wright. One of my favorite stories about him is that he created a complex of buildings, but he didn’t put any sidewalks in. Instead, what he did is let people use the buildings for a while and they walked in the grass between the buildings. They ended up wearing these paths where people would naturally walk. He waited to see what people would do before he put the sidewalks in.

It’s very tempting just to do things the way everyone always does them, but I think the Internet has given rise to so many people who say, “Hey wait, what if I did things this way?” Then they do a Kickstarter and everyone says, “Hey, this may be a really great way to do things.”

Have you had any difficult times in your life? What was your motivation to get through it?

One of my struggles is I that have some mild anxiety. It’s something that millions of Americans have, so if I’m able to talk about my anxiety and tell people, “Here’s what I’ve gone through,” and that I’m dealing with these things, that actually helps other people, too. It teaches you to be more vulnerable and willing to open up about those things—that it’s okay.

And what is the greatest achievement that you’ve had in your life?

That my book was on the New York Times bestseller list. That’s an achievement that was half work and half luck. I think that’s where a lot of achievements come from—you’re just in the right place at the right time. I always tell people that you work hard and you be nice to everyone. It might turn out really well, it might turn out just okay, but, at the end of the day, you can be proud. You don’t want to look back and think, “I stepped on everyone on my way to the top.” Being nice to people is more sustainable in the end.