04/19/2012 12:20 EDT | Updated 06/19/2012 05:12 EDT

Why I Didn't Meet Oprah


I was six feet away from her backstage. The entourage of security guards were distracted with other business. Now was my only chance to appease my obsession and jump into her arms. So why didn't I take it?

A month ago I got the call:

"Will you do a gig for free next month?"

"Which gig?"

"Emceeing Oprah's Lifeclass Tour stop in Toronto."

Thud (that's me hitting the floor).

"Eeeeey-y-yesssssughhhh" (that's me ugly-crying while I accept the job).

"See you on the 16th."

I was humbled, amazed, and incredibly grateful. Oprah's on my vision board. I quote Iyanla Vanzant regularly. Tony Robbins' tapes are the motivator that got me pumped to give comedy a try 12 years ago. I have most of Deepak Choprah's books. Hosting this event would mean meeting all of them. Highlight of my professional life, right? Yes. But for reasons I wasn't expecting.

If you've seen my website recently, you'll see that I'm making the shift from comedian to motivational speaker and comedian. The change being that I now want to make people laugh AND give them a few helpful take-aways. It stems from the learning I've done since recovering from postpartum depression and creative dry-spells. Over the last seven years, I have soaked up every piece of constructive insight in the fields of positive psychology -- going so far as to become trained as a life and group coach last summer. Every bit of work and training and practicing my skills as an entertainer culminated in the experience of hosting on April 16, 2012.

I arrived backstage at 7:30 a.m. at the Metro Toronto Convention Centre, bypassing the lines of thousands with my coveted backstage pass. "When will you meet Oprah?!?!" friends and fans texted. I was excited, but the Zen of performance prep distracted me, and I focused on my job. Make the audience laugh between speakers. I do that all the time -- just never for an audience of 9,000. The numbers weren't intimidating though, because Oprah's fans are my kind of crowd: eager, excited, and thrilled to be there.

I warmed up the audience with some comedy, then introduced Deepak Chopra. Then Iyanla Vanzant. Then Bishop T.D. Jakes. Then Tony Robbins. All of them are my idea of motivational royalty. I was so grateful. "Iyanla Vanzant is the Beatles of self-help," I tweeted. After each introduction I dashed offstage to sit by the monitors, soaking up their energizing messages: be grateful, forgive, push forward, make better decisions, seize your moment! The greatest minds and speakers of the self-help industry were on one stage, and in my opinion, they were flawless. Watching their craft of filling up the audience with possibility was awe-inspiring. They have "it." I think my mouth was agape for at least half of their talks.

Then there she was, red dress, perfect hair, smiling without worries, heading up to the stage to do what she does best. The Toronto crowd went just as crazy as you'd expect: we love ourselves some Oprah! After two hours solving people's problems in her validating way, Miss O graciously thanked the crowd and came backstage, wearing a glorious smile and satisfied aura. Which brings me to MY moment. I was standing six feet away, feeling pressure to get the bragging rights of having met one of the greatest icons of womankind. I stared for about a minute, mulling it over. Should I jump her? Meekly present myself? Ask someone backstage to snap a photo? I had an "aha moment." She had already given me her greatest gift: the impact of her message. And that far outweighs any chance to shake her hand. I turned and walked away, smiling.

I'll describe it this way: meeting the Beatles would have been cool, but it wouldn't surpass the experience of hearing their music. I was getting an up close encounter with my idols -- and watching them work and seeing their craft was the greatest element I will take away from the experience. "Thanks Oprah" I thought. "Thank you for all you've taught me. For your inspiration. And for bringing this incredible lineup to Toronto. No introduction necessary. You had me at hello."

Oprah's gift to her fans is delivered from stage; not in person. And it goes both ways. As Oprah said on the final broadcast of her show: "My greatest joy has been sharing this journey with you."