Cheryl Hickey’s ‘Aha!’ Moment With Oprah In Toronto

So as I lay on the floor playing Thomas the Train with my 2-year-old son Jaxson, I start day dreaming about how I will address Oprah. Will I say, “Hi O, Ms. Oprah, Ms. Winfrey’? Will I just run up and hug her, or will I just stand there and stare? When I suddenly snap back to reality with an: “All aboooooooard Mommy.”

Already this day is put into perspective for me, yet I can’t get a grasp on what is ahead as my ear is throbbing with an ear infection – which I think served me well in the end. Had I not had a rambunctious toddler and a wonky ear, I think I would have been really nervous. Truth be told I changed my outfit twice before I went down to the Toronto Convention Centre to watch Oprah run though her Life Class debut in Toronto.

Once we arrived we were greeted by this woman with the most beautiful smile and aura of ease, named Staci Collins Jackson. Must be an Oprah team thing! She informs me we will be getting five minutes with Lady O! I nearly fell over – since this was longer than I originally thought we would have. So with my producer Bob and Patricia beside me, we start talking about how we just need to do what we always do and just let it be natural.
We enter the room where Oprah is on stage with her team of producers going over the show. She watches every taped piece that is going to be aired for her fans and makes changes on the fly with compassion. Staci explains to me that Oprah insists on feeling every piece of the show and really understanding the emotion it will evoke or conversation it will start. To see someone so invested in a production from start to finish is so impressive and it’s great to see old school dedication and class.

We sit and watch Oprah laugh and chat with her team for probably two hours, when Staci turns around and says “Okay, lets go, she is ready.’ As we are walking up, all I can think is don’t pull a Tom Cruise and jump on the chair! So I walk up and say, “Hi, I’m Cheryl.’ And she says, “Hello what would you like to do?’ Taken aback, I say, “Whatever you would like to do!’ She smiles and asks if I’d like to sit down. From there the conversation just flowed. I remember while she was talking, thinking she has those kind eyes that that set you at ease and almost say, “Hello friend.’ That may sound corny, but she does.

After our chat, I couldn’t help but ask her to say my name in the “Big O’ voice! The way she has said Julia Roberts, John Travolta, Jenn Aniston’s and many others. She chuckles and fulfills my childhood dream of hearing her say my name! “Cheeeeeeeerrrrrrryyyyyylllll Hiiiiiicccckkkkkeeeeyyyy!’

As I get up to leave, she high fives me and takes my hand to her face and says, “I appreciate you, thank you.’

So as I am driving home, I have an “Aha!’ moment! It really hits me that I just interviewed one of my idols. I said this on Twitter last night, but have to say it again. If someone would have told back in the day, when I was struggling in my career that I would have an exclusive interview with Oprah, I would never have believed it. I have to admit, I don’t get starstruck when doing my job – never really have, but today that all changed.

Watch Part 1 and 2 below!





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