My year of "Living Oprah"

I spent 2010 following the advice of the talk show queen, based on a book about the same. Confused? Join the club

By Sarah Hepola

Published January 1, 2010 2:01AM (EST)


I don't recall exactly how I decided to spend one year of my life reading Robyn Okrant's book "Living Oprah." And by that I mean, I made the decision in a blackout. It was New Year's Eve, 2009, and my busty agent and I had been drinking red wine for hours at a bar in downtown Manhattan, brainstorming ideas for a book that, even in this wretched financial climate, would be a sure sell.

"What about one of those 'year in the life of's," she said, texting on her BlackBerry with one manicured hand while she ordered a second bottle of Malbec with the other. "Like 'Julie & Julia.' But for the recession."

It was my initial idea that I could spend a year figuring out how to pay my back taxes, an exciting first-person stunt I called "TurboTax Me." But that required money, the very commodity I did not have, the very commodity I needed to write a book in order to make. Couldn't they make it a bit easier on us authors? "My Year Spent Writing This Book for a Hundred Grand?" Would that sell? Who knew the vaunted profession of Ernest Hemingway and Virginia Woolf would prove so impossibly difficult to crack: Why couldn't I bankroll my exciting world travels as a single woman seeking romance and enlightenment, à la "Eat Pray Love"? You know, "Drink Snore Cuddle"?

My agent was hot to turn a piece I had written for an obscure online publication into a year-long experiment. For one week, I dressed like Betty Draper while adhering to all the tenets of L. Ron Hubbard. "Dianetics of a Mad Housewife" had gotten good buzz on Digg and Twitter, but after seven days of cone-shaped Maidenforms and excessive e-metering, all I got was a rash and a walk-on part on "One Tree Hill." If I was going to spend a year doing something, I wanted it to matter. I wanted to touch people. I wanted to comment on our tempestuous times.

"What about a year spent volunteering at a foster home for troubled teens?" my agent asked. "What about a year spent studying the intricacies of the healthcare debate so that you can contribute meaningfully to the discussion?"

We both burst into laughter. She started ordering shots: Herradura Silver, my downfall.

Not long afterward, my agent dug into her Birkin bag and unearthed a book that had arrived in her office just that day. Even in the bar's dark glow, I could see the tasteful purple, moss and magenta color scheme. "Living Oprah: My One-Year Experiment to Walk the Walk of the Queen of Talk," the title read. I knew from the airy white space of the cover, from the casual way the author crossed her legs on the front, this book was going to be hilarious and awesome.

"I don't even want to tell you how much she got for this," my agent muttered.

"A hundred grand?" I asked.

She raised an eyebrow. I was so naive.

I knew about the book, of course: Okrant, a funny and likable performance artist (is there any other kind?) from O's hometown of Chicago, decided to spend 365 days following all advice from the Oprah empire -- not just the television show, which coincidentally announced its imminent end just in time for her book launch, but also the magazine and Web site. Okrant would do what Oprah told her to do, think what Oprah told her to think, read what Oprah told her to read. The stunt, begun on her popular blog, had such honkingly obvious cultural cachet that it landed her a spot on the "Today" show and a profile in the New York Times Sunday Styles section before she'd even wrapped the book itself. And that was long before the book became a bestseller, Robyn Okrant got her own talk show and Meryl Streep won her sixth Academy Award for playing everyone's favorite black goddess.

I dragged my fingers over the glossy bas relief of the book title. "Nice font."

"Calisto MT," my agent whispered. "She's good."

Minutes before midnight -- before a new year and a new decade -- the evening fell like a heavy curtain over my eyes. Damn tequila. I woke up at 4 a.m. in my cramped Manhattan apartment, the book face-down on my chest. My agent had written a note and taped it where she knew I would find it: on the cheese in the refrigerator.

"Today is the first day of LIVING 'Living Oprah.' Remember, all great books end differently, but they begin in the same place: On Page One.

P.S. You owe me $85."

My heart felt light, free. At long last, I had a purpose, an organizing structure. Best of all, I had -- perhaps one day? -- a book deal. I would spend a year reading Robyn Okrant's "Living Oprah," learning everything she could teach me about the self-help industry, about other women, about Oprah Winfrey -- about myself. I clutched the book to my chest, feeling that my adventure had already begun.

Then I ran to the bathroom and threw up. I was really hung over.


What a month! I bought my blog URL. (Imagine my delight to discover that "" was available. Is that fate or what?) I started a Tumblr account, posed for my (rather comely) author photo and posted an elaborate stop-motion animation trailer of the book's themes on YouTube that's already been praised by BoingBoing.

Next month: I read the book!


It was time to tell close friends about my "little experiment." I gathered my three besties -- my gorgeous but endearingly slow friend Lisa, my gay friend Thomas and my busty agent -- into my comically tiny Manhattan apartment in a questionable neighborhood and plied them with blueberry bars, Origins' Ginger Souffle and copies of "The Bridges of Madison County."

"You haven't started the book yet, have you?" my agent whispered as I poured out four fingers of Herradura Silver.

I cringed. "Can you tell?"

I dimmed the lights and played the stop-motion animation trailer for them.

"You look foxy!" Lisa said when my author's picture popped on the screen.

"Did you get lipo for that picture?" Thomas asked, and Lisa elbowed him in the ribs.

Ten minutes later, the trailer ended, the "Don't Stop Believing" theme music finally faded, and I stood before them, feeling a bit nervous and a bit excited.

"So wait a minute," said Lisa, munching on her blueberry bar. "Is this like the time you decided to eat only orange food for one year?"

"No, that was a diet," I explained.

She nodded. "Is this like the time you tried to stop drinking tequila for a year?"

"No, that was ... a drink diet," I explained.

Thomas threw his blueberry bar in the trash. "Is this like the time you stopped sleeping with strangers for a year?"

"I never did that."

He shrugged. "Just saying, it's not a bad idea."

My agent patiently explained to all the opportunity that awaited me. She talked about the support and humor I would need over the next nine months. She made the project sound noble, beautiful, brave. Lisa couldn't take her eyes off her, and even Thomas looked impressed. I was so inspired!

And then she took 15 percent of everything we had in our wallets.


Very exciting development: An acquaintance in Latvia with mob ties has sold the Eastern European rights to my stop-motion animation trailer! My agent is talking to Bristol Palin about starring in the full-length feature version of the trailer, to be directed by the illegitimate son of Chevy Chase! Everything moves so fast here in the fast lane.

Next month: I start writing the book!


Oh my god, you guys, writing is hard.

"Too bad you didn't make a stop-motion animation trailer about sitting around in your pajamas all day and eating bacon cheese," Thomas said the other day. Sometimes I really hate Thomas.


"I know what you need," Lisa told me one evening as I sat, depressed, staring once more at a blank screen. "I know what Oprah would want for you."

"Bacon cheese?" I asked hopefully.

"No, silly," Lisa said, pulling out a saucy dress from the back of my closet. "Dancing!"

Ooof. I couldn't go dancing! Dancing was a celebration, and I had nothing to celebrate: Six months into my big project, and I had yet to even crack the spine of the book. What had I gotten myself into?

"I've watched Oprah Winfrey," Lisa said, plopping down beside me on the sofa. "Like, a lot. And what Oprah Winfrey wants more than anything is for you to live your Best Life. Not a life of sitting around, listless, in prison clothes."

"They're pajamas," I corrected her.

She wrinkled her nose. "Honey, they're really not."

Maybe Lisa had a point. She did, at the very least, have a small glass of Herradura Silver, which I sipped while weighing my options. I could stay home and bang my head against the laptop monitor once more. Or I could go out and live my Best Life, enjoy all the delicious fruits Big O wants us to savor: Laughter, connection, Lady Gaga.

"OK, I'm in," I said.

I woke up the next morning hideously hung over and found a note taped to the cheese:

"Don't panic. His name is Cesar. He's very nice. He does speak a little English.

P.S. You owe me $125."


It's amazing how much you can learn about a person when the only words you have in common are "dog," "smile," "cucumber" and celebrity names. I don't want to jinx it, but I do think I'm in love with Cesar. And we both adore Angelina Jolie! What are the chances of that?


ZOMG I think Cesar's moving in!!!!!!!!


Tonight my agent hosted a dinner party for the Asian release of my stop-motion animation trailer, which found a surprising popularity on Japanese smut sites, due to a cultural misunderstanding of the term "The Big O." Bristol Palin was there. Cesar was there. And, of course, Lisa and Thomas were there.

"Here's to the next great American book!" my agent said, holding aloft her wine glass.

"Oooh, who's writing that?" Thomas asked, and Lisa elbowed him in the ribs.

I blushed with all the attention. Bristol Palin is so much prettier in person, just FYI. "I want to give a special thanks to all of you," I said. "To Bristol Palin, to my agent, to my friends, to my special cucumber." Thomas did a spit take, and Lisa handed him a napkin. "Without your support, I never would have made it seven months into this crazy journey. Only three more months to go! I love you -- and more important, Oprah loves you."

"Angelina Jolie?" Cesar asked. It was an awkward addendum, so I drank heavily. Apparently, I owe Bristol Palin $35.


Did a poet once say that October was the cruelest month? If not, why not? Surely that poet wasn't trying to write a book about reading a book about a year of following the advice of Oprah Winfrey. And if not, then why not?

Those are the opening lines of my book. What do you think?


Cesar and Bristol Palin have fled to Puerto Vallarta. How was I supposed to know she was fluent in Spanish? There are no words to describe how depressed I am except, possibly, really really depressed. My book is going nowhere. My boyfriend has disappeared. Lisa and my agent are in love, having both decided at the age of 35 that they're lesbians -- "fauxmosexual," Thomas called them, which landed him a book deal based on slang words used by salty gay men to describe slutty female behavior.

Oprah, why hast thou forsaken me?


With nowhere to turn, I did what I probably should have done back in January of 2009, what I'd spent 11 months avoiding: I opened "Living Oprah," and I began to read.

P. 1: "I can feel adrenaline pumping through my body. I'm moving and talking a mile a minute. I've got the same buzz that I usually feel on opening night of a new play, although it's noon and I'm not going onstage."

I knew that feeling! I knew exactly what she was talking about. My heart started racing. I turned the page. Then the next. It was as though all the air had been sucked out of the room, as though Oprah herself had reached down from that Harpo Studio in the sky and placed her palm on my very heart. Tears streamed down my face, as I read page after page of hilarity, of poignancy, of awesomeness.

P. 6: "Do Oprah and I have anything in common, or have we drifted apart?"

P. 37: "And speaking of fecal matter, we've all been urged on the Oprah show to strive toward S-shaped fecal matter."

P. 183: "I have to give a shout-out to Reggie, Oprah's makeup artist."

I stayed up all night reading -- laughing, learning, loving. Why had I decided to write a book preying on this book, so obviously a complete work in and of itself? What a cynical exercise mine had been. What a pathetic gesture of financial and professional jealousy. Could I not find the courage and strength to write my own story, instead of picking and tearing at the flesh of someone else's literary carcass? Had I not the originality of thought, the creative energy to make my own characters, my own adventure? Was I not a writer, after all? The wise words of my busty agent came floating up to me:

All great books end differently, but they begin in the same place: Page One.

Then I remembered that I still owed her $85. Shit.

But I opened my laptop, and I began to type. The words flowed from me like sweat, my fingers flying across the keyboard, each letter a joy to type.

"I don't recall exactly how I decided to spend one year of my life reading Robyn Okrant's book 'Living Oprah,'" I began. "And by that I mean, I made the decision in a blackout."

It took me a year. But finally, I was on my way. 

Sarah Hepola

Sarah Hepola is the author of the New York Times bestselling memoir, "Blackout: Remembering the Things I Drank to Forget."

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