The Long Goodbye: What's it like to work for Oprah?

On 1.1.11 Oprah launched the Oprah Winfrey Network (or, OWN), which promises to be a “24/7 cable network devoted to self-discovery, to connecting you to your best self and to the world.”  OWN takes over the Discovery Health Network with entirely new programming and on the 12/29 Oprah Winfrey Show, she devoted an episode to the launch.  But only one program was previewed: Season 25: Oprah Behind the Scenes.

For those of you keeping track, here’s what it boils down to: Oprah used The Oprah Winfrey Show to promote a new reality series about The Oprah Winfrey Show, to air on the Oprah Winfrey Network.  That’s a whole lot of Oprah!

Previewing clips of the series (and later watching myself), I was struck by the lack of ego Oprah displayed when interacting with her staff and how the environment seemed oddly relatable to anyone who has worked a stressful, corporate job.  Staffers fret over:

…pitching ideas: “We’re not delivering the type of ideas that I would present to Oprah. I’m overwhelmed. My stomach is in a ball!  I’m going to throw up!” 

…wanting to impress their boss and do their best work: “you [Oprah] saying that during the last season ‘we’re going to knock your socks off’….well, I got a pit in my stomach!  The bar is already set so high!”  Oprah responds, “You know I had a pit in my stomach after I said it too!” 

…figuring out work-life balance: “I think it’s a high-pressure job with long hours and it’s always a choice between children and work.”

And that’s where an interesting theme emerges, particularly for the women staffers: making sacrifices. In between previews of the behind-the-scenes reality series, Oprah conversed with her staff (who made up the full audience) and encouraged them to express themselves openly about their job experiences.  A significant portion of her staff are women, many with children, and all discussed the sacrifices they’ve made for the show.  The women with children acknowledged the challenge of being a working mom and often repeated variations of the same quote: “I had to be OK with making sacrifices for work.  I hope I inspire that passion in my children.”  Oprah sincerely praised them all for showing up, working long hours and sacrificing their personal lives, but clearly believed it was all necessary.  Which made me wonder if it’s difficult for women who don’t have children (like Oprah, and full disclosure: me) to fully understand those sacrifices.

My female friends and I universally interpret “having it all” as being able to reach your full potential in both your personal life and work life, and we started out in our twenties feeling like we’d be the first generation to achieve it.  As we entered our thirties, I watched many of my friends who had children become discouraged, even depressed by their perceived lack of “full” achievement in either area as a failure.  Conversely, my friends and I who didn’t have children often felt—fairly or not—like work became all-encompassing, because we didn’t have a “legitimate” reason to leave or stop.  We discuss this often, and usually come to the conclusion that it’s impossible “to have it all.” At least by our definition. Unless, maybe, you are Oprah.

Yet even within this discussion, it was apparent that all staff members who worked for Oprah enjoyed their employment with big O tremendously.  Oprah represents herself as an authentic boss, who talks shit with her staff openly, directly, and warmly.  She also talks shit literally, as shown in this clip.

“It’s no small thing we’ve all worked you this long,” said a senior producer, acknowledging several staff members who have worked for Harpo for 10-plus years.  I think they’d continue as long as she wanted to keep going.

Tomorrow we’ll look at a sampling of OWN’s programming schedule.  More Lisa Ling!  Less Doctor Phil!

by Jennifer Tress
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