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The Root: Walking 8 Miles A Day For Winfrey's Wink

Oprah Winfrey ended her talk show last week after 25 years on air. Winfrey is also the founder of <em>O, The Oprah Magazine.</em>
Mary Altaffer
Oprah Winfrey ended her talk show last week after 25 years on air. Winfrey is also the founder of O, The Oprah Magazine.

Helena Andrews is a regular contributor toThe Root .

I met Oprah once. Well, actually, to be clear, I met Oprah, but I'm entirely positive that she didn't meet me.

In the fall of 2002, I had a fresh diploma from Columbia in one hand and a fistful of bills in the other. For the past four years, declaring myself an English-literature and creative-writing major seemed extremely old worldy.

And then the real world happened. My third (yes, third) of the rent was $550 a month, plus utilities. My ability to read and write like a pro, though a prerequisite for life, wasn't the "alakazam" to the good life or even a paying internship.

Sept. 11 was the starting bell to our senior year. We were the graduating class of the country's collective reality check. Things weren't going to be easy. Whatever path you thought you were on at 8 a.m. could be annihilated by 10 a.m. An Ivy League degree and a decent "phone voice" weren't enough to get my foot in the door half the time, much less the actual job, because there weren't any.

So when a mentor suggested that I give Oprah's magazine a try, I thought, "Yes, of course; right after Maya Angelou copyedits my resume." Then I got the internship. And then I found out it paid approximately 5 dollars and 15 cents an hour. I was expected to work 40 hours a week (no time for a lucrative side hustle and sleep), which meant that after taxes, my weekly take-home was about $188. With less than $200 for food (or anything else), a monthly MetroCard for New York City Transit was out of the question.

So what did I do? I walked. I walked from our three-bedroom apartment on 128th Street in Harlem to O magazine's offices on 53rd Street. Both ways. Five times a week. Once, in the rain with a cheap $5 umbrella and soggy ankle boots. I did it to pay my dues. I did it because I needed a damn job. I did it for Oprah.

It wasn't until my last month at O, the Oprah Magazine that I finally got a glimpse of her. She was like the Great Oz of our office. People talked about her in hushed tones as if she were listening in all the way from Chicago. I saw Gayle King on a regular basis. She was the magazine's direct line to Oprah, almost like how a Catholic priest connects his congregation to Jesus. She spoke for Oprah in editorial meetings, saying things like, "Well, I know Oprah is concerned with ... " or "Oprah feels as if ... "

I covered Gayle's phones once during her regular assistant's lunch break when a man named "Mr. William Bumpus" called. First off, that sounds fake. Second, it was part of my job to screen for weirdos, of whom there were thousands. People would call on a consistent basis, not with questions but with very long comments that spiraled into soliloquies that ended in, "So if Oprah would just give me $100,000 ... " Mr. Bumpus had to be vetted.

"May I ask what this call is regarding, sir?" My office voice is legend. I can sound equal parts sweet Peggy of Mad Men and commanding Aunt Entity of Mad Max. None of those voices worked on Mr. Bumpus. "No, you may not."

Pissed, I trekked into Gayle's office to tell her that a man was on the phone who had very politely told me to mind my business. "Well, who is it?" she asked, unfazed. I figured I'd get to "Bump-" before she laughed it off. This was clearly before Wikipedia.

"Oh, that's my baby daddy," answered Gayle with a deadpan that told me that a), she knew she was being funny, and b), she'd probably said "baby daddy" more than once in her life. I was awestruck. I didn't need to meet Oprah because her BFF was this cool.

Weeks later, the eagle finally landed. Instead of huddling near the front desk like all the other should-be workers, I was stuck covering the phones at the receptionist's booth outside the office. I wouldn't even get a glimpse of Ms. Winfrey. For the past three months, I'd walked nearly eight miles a day just for the privilege of putting Oprah's name on my resume. I had the emaciated figure to prove how hard I'd worked, but somehow, seeing her would make the whole thing more real.

I was busy with a bowl of Top Ramen when I got the call that Cathie Black, then chairman of Hearst Magazines, would be stopping by . Could I let Oprah know? Could I! I smoothed down my H&M skirt and marched into the art department like I had something super important to say.

Whatever super-important voice I planned on using escaped me as soon as Oprah Winfrey looked up at me expectantly. She was a short giant. Her eyes were even bigger in person. I waited a beat before blurting out, "Cathie Black is coming!" with a squeak that had been on reserve since middle school. Oprah looked at me for just a half second more, gave me a little wink and went back to what she was doing.

A month later, I decided that I'd make my living writing as a journalist, and I've spent the last decade doing just that. Not because Oprah winked at me that one time when I was 21, but because I'd walked miles, risked malnutrition and come close to eviction for a calling that I wasn't sure I had the guts for.

But I did. As Oprah said on her final show this week, "Everybody has a calling. And your real job in life is to figure out what that is and to get about the business of doing it."

Copyright 2020 The Root. To see more, visit .

Helena Andrews