I just got off the phone with one of my daughter-girls from my school in South Africa. She's attending college in the U.S., and this was one of many, frequent conversations. I've had a hand in raising her since she came to the Oprah Winfrey Leadership Academy for Girls at the age of 12, helping to shape her view of how a young woman born into poverty might break the cycle of institutional oppression and free herself to soar. She, like almost every student I've ever interviewed, came to school with hopes of creating a better life for herself and her family.

"Why do you want to come here?" I always ask. "To get a good education, ma'am, so I can build my grandmother a house." "So I can help my mum." "To help my brothers and sisters go to school." "So I can feed my family."

This desire, though admirable, usually leads to guilt and eventually becomes a burden—hence the long conversation I just finished.

I said to my daughter-girl—who works part-time at a minimum-wage job to be able to buy essentials for herself, but is now conflicted about how much money she should be sending home—"What do you think you owe your family? Should it be everything you earn, at the expense of your own needs? Should you send them money every time they ask?"

This daughter-girl suffers from both fear of failure and fear of success. I understand each. The trauma of poverty, of never having enough, makes you think you're not enough.

So I asked her the big question: "What does success look like for you?" And: "Do you have what it takes to get there?"

I know she does. But I also know I can't make her know it.

Every person has their own big questions that no one else can answer. And this year we will pose 12 of them, one every month. They are all questions I've thought about deeply and know my answers to. I also know my answers will keep evolving.

One lesson I learned from all my years of interviewing is that the key to getting the answers you need lies in asking the right questions.

When you ask people how a certain experience or event made them feel, their response is usually a surface one. "It felt great/amaaazing/bad/sad." The question doesn't compel them to go further.

When you ask how that same experience impacted the way they see themselves, another level arises.

This happened to me recently after seeing Springsteen on Broadway. I came away moved to the marrow of my being and for days could not articulate what exactly I was feeling.

Whenever someone asked "How was Bruce?" I'd just start to tear up and then use some superlative description.

Finally, though, I asked the right and bigger question—not How was the performance? but What happened on stage that had such a powerful impact on the way I saw him—and, more importantly, myself?

Photo: Bruce Alikas/Getty Images

It was this: He was able to break down the human uniform we all wear and speak directly to the interior of me. So much so that I felt my heart aching and my soul resonating, yearning for more. It was the definition of a spiritual experience. And ever since that beautiful encounter—Bruce on stage, alone with his guitar, poetically revealing the essence of his life, my life, all life—I've been more open to all forms of poetry. I read a poem or two in the morning before working out, and I see poetic forces throughout the day: in fallen leaves and empty branches, in cloud formations, in people bent over tables in cafés, deep in conversation.

What happened with Bruce on Broadway was artistic expression at its best. I felt as if this journey we're all on—of questioning and discovering—just got expanded. I felt deepened, widened, by the singing of it.

And here we are at O this year, attempting a similar feat minus the vocals and guitars. Just life's big questions. Hopefully, they'll lead you to sincerely ponder, as my daughter-girl is pondering, what makes you you. And why your presence on earth right here, right now, so truly matters.


Next Story