'What's the Worst That Can Happen?' And Other Life Lessons From Oprah's Vogue Feature

Image via Getty.
Image via Getty.

In all her years as the queen of all media, Oprah Winfrey has shared a life’s worth of life lessons, whether whispering or screaming them, and now she is in a Vogue feature story, still forcing us to learn.


Because there is no other way for an Oprah profile to begin, this Oprah profile in the September issue begins with the sentence: “It is the golden hour in the Promised Land, and we are walking down Hallelujah Lane, going to see the Apostles.” As you guessed, the Apostles are trees, and the Promised Land is where Oprah lives, a 65-acre estate in California. So, quite small.

Oprah bought her neighbor’s portion of land when the neighbor died, so her property is even bigger and features “a forest of mature oaks” and “a fountain the size of a lake that shoots water to the heavens” and a teahouse and a rose garden and a duck pond.

Oprah may be the most optimistic person on the planet, but she has at certain points mistimed her optimism, like when she tweeted about breathing after Trump’s election win. She cannot help speaking in self-help language, and so there are multiple life prescriptions throughout her Vogue feature, written by Jonathan Van Meter.

Oprah has learned, for one:

“I have learned that being-fully-present thing. I am 1,000 percent fully present.”

She also learned about the importance of gratitude after obsessing over box office sales of her film Beloved, which contributed to her depression at the time:

“That’s when the gratitude practice became really strong for me,” she says, “because it’s hard to remain sad if you’re focused on what you have instead of what you don’t have.


And she learned:

“It taught me to never again—never again, ever—put all of your hopes, expectations, eggs in the basket of box office. Do the work as an offering, and then whatever happens, happens.”


After a 28-year gap where Oprah did not act (between The Color Purple and Lee Daniels’ The Butler), she’s acting a lot again. Her philosophy:

I was intimidated by the work, but in the end, what’s the worst that can happen? You get bad reviews—but in the age of Trump, it will be over in a day.”


By the way, go to New Zealand:

“I am telling you: If you want to expaaand yourself as an individual on the planet Earth, New Zealand’s the place to go. The people are 100 percent present. They are not walking across the street on their cellphones. Every single corner you turn, there is some breathtaking something or other going on: Lakes! Glaciers! Eagles! It’s crazy.”


Here’s how Oprah believes (knows) you will evolve in your 40s, 50s and 60s:

“In your 40s, you’re coming into it, you’re intellectualizing things, and you kind of know it and you feel it,” she says. “But there is a deepening and a broadening and quickening of the knowing that happens in your 50s. Maya Angelou used to say to me, ‘The 50s are everything you’ve been meaning to be.’ She looks at me over the top of the nerd-chic glasses she favors these days. “You’d been meaning to be that person.” She laughs. “By the time you hit 60, there are just no . . . damn . . . apologies. And certainly not at 63.”


One point that Oprah has made in a variety of ways over the years is that people have a desire to be seen:

“There’s not a human being alive who doesn’t want—in any conversation, encounter, experience with another human being—to feel like they matter. And you can resolve any issue if you could just get to what it is that they want—they want to be heard. And they want to know that what they said to you meant something...People just want to be seen; they want to be validated.”


You have to know when to end a good thing:

“I didn’t want to be the person chasing a phenomenon. And that is what the Oprah show was. All the right elements came together at the right time. That won’t happen again. People would ask me, ‘Who will be the next Oprah?’ And the answer is: ‘There won’t be.’”



Live life on your own terms.

On marriage and what if she’d married Stedman:

“We would not have stayed together, because marriage requires a different way of being in this world. His interpretation of what it means to be a husband and what it would mean for me to be a wife would have been pretty traditional, and I would not have been able to fit into that.”


Go forth about the day and about the world now. You’ve been cleansed.

Culture Editor, Jezebel


JujyMonkey: unstable genius

We would not have stayed together, because marriage requires a different way of being in this world.

Er, no it doesn’t. You treat your partner with love and respect, the same way you do if you’re not married.

But I don’t have a 65 acre estate with a tea room and a duck pond, so what do I know?