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What I Learned When I Asked 7 People One Of Life’s Hardest Questions

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Meet Jenna Mack. She is the creator of In the Grey, an interview docu-series that explores the unexpected sides of people and topics we think we already know. She wants us to move beyond just the 'black or white' perspective and see the grey, as in all of life’s beautiful complexities as these are what truly defines us, and what ultimately connects us.

So how did Mack end up in a cool job like this? It took a bit of soul searching. After college she moved to Europe for 10 years making connections with people in these different countries and learning about their customs which were quite a change from how she had grown up. When she returned to the U.S. she landed a plumb job as a producer on Charlie Rose. 

This also gave her great insight into how people tick. "It was an invaluable experience and opened my eyes to the world of media and the power it has," she told Levo. "I have a natural passion to connect to and understand people; how they live, why they feel the way they do, what they believe. I didn’t realize until I became a producer that media was a perfect outlet for what has always driven me." 

She left Charlie Rose knowing she wanted to build a platform centered on connection and thus In The Grey was born.

But how do you get people to reveal those "aha moments" and deep confessions without making them feel weird or stressed? When creating an interview segment she said she seeks topics that might have an inherent tension or contradiction. Once the topic is selected they interview three people who represent a different angle or perspective of that topic.

Her signature question is "What’s the one true thing you know about yourself that no one taught you or told you?" This definitely doesn't come with a one-word answer. Mack said, "It’s a powerful question because it cuts through the layers of what outside experiences or other people have taught or told us about who we are and instead gets to the essence of who we know ourselves to be. 

In some ways, I’ve been surprised by how forthcoming people are in answering that question and how some haven’t hesitated or had to think about their answer first." She called out singer Darlene Love as a prime example of this. "When I asked her that question, she intrinsically knew the answer was that she’s a survivor. Or [transgender model] Aydian Dowling, who said he always had a strong personal sense of right and wrong. "I’ve also come to learn how the question serves as a mirror to whom I’m interviewing and how they live their lives. Their answers turn out to be the encapsulation of their journey. Aydian didn’t realize it until he answered that question that his innate sense of right and wrong helped him transition. He felt strongly that transitioning was the right thing for him to do and not transitioning would have been the wrong thing for him."

But it is these questions that produce the most beautiful stories. "I try to relate to people on a personal level and therefore try to ask questions that will find their way to the essence of who the guests are. But it’s more than just about asking the best questions if there even are any. It’s equally important to create a sacred space, an environment that feels safe. I have found that people really do want to tell their story but they want to trust that they will be heard and be understood. Everything I do is in service of that."

(Photos courtesy of In the Grey, Photo by Emily Morter on Unsplash)

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