I made Oprah cry and the reason why has become a major life lesson for me

Oprah Winfrey attends the European Premiere of ‘A Wrinkle In Time’ at BFI IMAX on March 13, 2018 in London, England. (Photo by John Phillips/John Phillips/Getty Images)

This week has been an emotional rollercoaster for me. The kind where you wish you could take a personal day (or week) off and just crawl into bed until everything starts making sense again.

Which is why when I was assigned to attend the press preview of “Watching Oprah” at the Smithsonian National Museum of African American History and Culture on Wednesday, I was genuinely excited and figured it would be a sure fire way to lift my spirits.

Like most little Black girls who grow up and went on to work in the media, Oprah Winfrey has always been one of my biggest influences.

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When I first came to this country I was shy, quiet, and scared. Both of my parents were still back in their homelands, (mom in Haiti, dad in Cuba) and I was sent off to America to have “a better life.” The plan being that when they saved up enough money, they would eventually come join me, as is the case with most immigrant stories.

This was in the 80s when Afro-Latinos weren’t really considered a thing.

As a result, the kids at school made fun of my accent to the point where I started practicing how to speak properly like the white folks I saw on the news. My aunt, who was my designated guardian, was always at work, leaving me home alone with nothing but a pile of grown people books I was too young to fully understand (but I read them anyway). And I quickly became aware that I was relegated to the “other” box and didn’t quite fit in with anyone else.

Shame soon became my best friend.

I was convinced that I wasn’t good enough, pretty enough, or smart enough to be accepted by anyone. In my young mind, if even my parents hadn’t bothered to stick around, that surely meant I was damaged goods.

And then one day I saw Oprah.

She was my color, and a little chubby like me, but there she was with a microphone, speaking to the camera, and smiling at an audience full of people, emanating loads of confidence as if she belonged there.

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I still remember how big my eyes got that day, because my auntie came in, laughed when she saw my stunned expression, and then asked, “What in the world are you watching?”

This would turn out to be an ongoing joke in our home. Every time auntie would come home she’d ask, “You watching Oprah again?”

And to be honest, more times than not, I was. A habit that continued right until Stevie Wonder sang, Isn’t She Lovely to Oprah during her series finale.

I Surrender All

Flash forward 30 years later and I’m at the Smithsonian to take this tour of a new exhibit dedicated to the life and legacy of Oprah, which quite brilliantly maps out step-by-step how she built her empire. I was moved, and inspired, but there was also a nagging feeling of doubt tapping at the back of my mind.

During the last three years, my mentors and advisors have all been pushing me to work on a book, not to mention the script idea that’s been haunting my sleep as well. My friends were constantly asking why I seemed to shrink away from the limelight, while my counterparts are out here making moves and becoming masters at self promotion.

The truth is I had been intentionally dragging my feet.

In this era of social media influencers and IG fame, I have watched more than a few of my favorite people get eaten up by fame and turn into things I didn’t quite recognize. My fear of becoming one of those folks who fell victim to their own hubris was palpable. So much so that it has made me turn down opportunities that could have been life altering.

In a nutshell, I’d been playing it small, but standing there in that exhibit, seeing all that Oprah had accomplished by NOT playing small, I felt an unbelievable and quite unexpected wave of shame. A feeling I pride myself on being pretty immune to in general.

“God, have I made a mess of things?!” I blurted out loud, startling the older woman standing next to me who was looking at the glass case that had Oprah’s old Harpo Studios desk and a proud display of her Emmy’s inside.

Seeing the look of concern in her eyes undid me. Suddenly, I started to tear up and scrambled away looking for an exit.

Anyone whose ever had a panic attack will tell you that when it happens it feels like the most urgent thing in the world. For a brief moment I legit thought I was going to lose my marbles right then and there. But instead, I did what I remembered Oprah said she had done right after auditioning for The Color Purple.

I surrendered.

I took a series of deep breaths, and said (in my head this time), “Universe, I surrender. Please just send me a sign that I’m on the right track. And that it’s not too late.”

I must have looked all types of crazy standing there with my eyes closed because when I opened them, I noticed the sweet old lady from earlier was quietly watching me, still visibly concerned. I braved a smile to let her know I was ok and then turned to leave with whatever shred of dignity I had left.

An Honest Message

Right before I hit the exit, I noticed a guestbook, asking visitors to share a message explaining the impact Oprah has had on them. Without even pausing to think about what I wanted to write, I started scribbling.

“Oprah Winfrey is the reason I love myself so fiercely and know that my voice matters in this world”

The words came through me so fast it was like I was reading them for the first time. It felt cathartic, like a reminder of who I really was despite this uncharacteristic crisis of faith I was having.

Afterwards, I went home, had another good cleansing cry, and wrote an article about how amazing the exhibit had been. The next day, I woke up to a text from a friend who sent a screen shot of my note to Oprah that had somehow aired on CBS!

There aren’t any words to describe how surreal and bizarre it felt for the next 20 minutes while I tried to make sense of what had happened that morning. A quick Google search revealed that Oprah and Gayle King filmed a segment for CBS This Morning of the two of them walking through the exhibit for the first time.

They laughed and chatted as they went down memory lane looking at all the pieces of Oprah illustrious past, until finally the museum’s director Lonnie Bunch led them to the notebook, where the messages had been written.

Right before my eyes, I saw Oprah reading the notes and when she got to mine, something in her clicked. She paused and before I knew it, she began to cry after reading what I had written in the exact same way I’d been crying when I wrote it.

It was as if I was watching a mirror image of myself from the day before.

As a writer, I know words carry a frequency of power, but to see it manifested in this way was a first for me. Not to be dramatic but I felt God in that moment. I tangibly received the sign I’d been waiting for, for so long. 

And just like that, I got my mojo back.

What is meant to be, will be

After I geeked out and told my coworkers about it, I was asked to write about my experience and I said no.

That moment of synchronicity had been deeply moving for me, but Oprah is a BIG deal so I figured it had probably been a lot more fleeting for her. It didn’t feel right milking the exchange for more than what it was and as someone who tends to write about social issues, doing a whole piece on myself felt conceited (and a bit boring).

In fact, I had just finished giving my managing editor a speech about why it felt wrong to write a piece called, “I made Oprah cry” when I looked into my inbox and spotted a message from OWN.

What I read when I opened it floored me.

“I wanted to reach out to let you know your message in the guest journal yesterday at the new “Watching Oprah” museum brought Ms. Winfrey to tears as she walked through the museum for the first time,” the letter began.

“I wanted to personally reach out and thank you for sharing the impact she had on you, and let you know of the impact you in turn had on her. We appreciate you visiting and your piece chronicling the new exhibit was wonderful.”

At this point, my eyes were big as saucers again, kind of like the way the were the first time I saw Oprah on TV, except this time it was because she had seen me too.

The message then went on to share a press release about the exhibit in which Oprah explains why she had the reaction she did.

”Oprah Winfrey says she cried when she got to the end of the Smithsonian museum exhibition that bears her name because a journalist had written in the guest book that “watching Oprah every day is the reason I love myself so fiercely.” Winfrey says it reminds her of a letter she got in 1987 from a fan who told her “watching you be yourself every day makes me want to be more of myself.”

“It made me cry because it is full circle that the mission was accomplished,” Winfrey says. “The intention was fulfilled, and that was to be a mirror for people to see themselves, in other people, in others’ stories; and by watching those stories of other people, be lifted, be inspired, be encouraged in a way that makes you think you can do better in your own life.”

Ok, so even now, I’m tearing up again as I write this ya’ll.

The girl who wrote that note in 1987 could have been me. That was my story and without even noticing it, I had grown up into exactly the kind of women I had always wanted to be.

Aside from getting that overwhelmingly clear message from God, this whole experience has also put to rest my greatest fear. All this time I have been dragging my feet, and holding back on completely reaching for my dreams because I was scared that fame, or too much attention would turn me into someone I didn’t like or recognize. But here is one of the most famous people on the planet taking a moment to let me know that she appreciated the impact she had on my life and on all of our lives.

If Oprah Winfrey can still be that grounded and grateful for her blessings, after all that she’s accomplished, then I’m starting to think I have nothing to worry about, even if I did choose to take the scenic route.

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Also, at some point, I need to call my aunt who always teased me about watching The Oprah Winfrey show and tell her what happened. Clearly it all worked out, eh?

Check out the full CBS This Morning segment below, paying special attention at the 5:30 min mark. lol


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