I spent my last summer before starting college asking a lot of people some very personal questions. It all started in the last week of my senior year of high school. I was starting to get nervous as the school year neared its end. I’m a huge nerd and the idea of spending the two months without any kind of intellectual stimulus was horrifying to me.

So, I reached out to my teachers--both the ones I had for my senior year, and the ones I had in years prior. Most of my teachers suggested things like learning a new language or reading classic books, but it was my former middle school math teacher and high school track coach, Michael Karthas, who came up with the idea that really piqued my interest.

When I approached him about a summer project, he said he was actually thinking of doing his own project, and that he’d welcome my collaboration on it. He wanted to interview successful people about their backgrounds and their opinions on things like success and grit. We ran into a problem almost immediately: how does one determine who is successful?

Success is often subjective. Mr. Karthas decided we should just come up with a list of questions and ask people we thought might be interesting to talk to, with no restrictions other than that they had to be older than 18. He said the theme would come to us as we went through the interviews. This made me nervous. I have always been very Type A, and going into this project with a loosely structured plan and no concrete concept made me skeptical.

We came up with a list of questions. Most were broad, but not too personal. Things like, “Define success.” “What makes you satisfied?” “Do you have any siblings? Do you have a good relationship with them?” “How would your high school teachers define you?”. Questions were designed to give us a complete, but superficial idea of who these individuals were. We also came up with a list of people we wanted to interview. They were teachers and friends, coworkers and family. Anyone we thought might have an interesting story or perspective.

We quickly discovered that everybody has an interesting story or perspective, so the requirement shifted slightly. We talked to anyone who was introspective enough to reflect deeply on the questions we asked, and we developed our questions. They grew deeper and more personal. Things like “Who do you owe an apology and why?” and “Are you holding on to anything you need to let go of?”

The project quickly became reminiscent of Humans of New York. It was cathartic, both for the people sharing their stories and for me to listen to them. Many of the people we talked to were heroes and role models of mine, and hearing their stories only humanized them and made me respect and admire them more. People I thought exemplified perfection and good fortune had so much more depth than I could have dreamed. They struggled and thrived in ways I never knew before interviewing them. It allowed me to connect with these people in a truly meaningful way. And, for their part, the interviewees were able to share their burdens and reflect on their happy moments. They were given a platform to really examine themselves and reconnect with the truths and memories they held closest to them.

We began every interview by assuring the subject that they did not have to answer any questions they found too intrusive or uncomfortable. And yet, not one of the 20-something people we talked to refused a single question. They shared heart-wrenching stories of loss and failure, and disclosed beautiful and inspiring anecdotes about family, love and strength.

Throughout the process, the one thing people kept asking me was, “What’s the point of this? What are you planning to do with this information?” And I told them the truth, that there was no point. That we asked the questions because we wanted an excuse to have these deep, thought-provoking conversations that people don’t usually have with each other. There’s a level of fear associated with big personal questions. Everyone is so scared to cross some invisible social boundary that they never get to know the most hidden pieces of the people they care about.

I would often fret to Mr. Karthas that maybe we were pushing people too hard, and what right did we have to ask these questions? Mr. Karthas would just shake his head and tell me, “Catherine, people don’t say what they don’t want to say.” In other words, people came out with that information because they wanted to share it with someone else. Each answer revealed a piece of their past and offered an explanation for their existing character. Think of everything that has happened in your own life, and how much of it has impacted your growth. Wouldn’t it be something if you could share with someone a comprehensive account of who you are today and how you got where you are? So, don’t be afraid to ask the big questions. You might be surprised at how much you learn.