What Do You Really Want? The Question Oprah Asked That I Can't Put Down

Oprah flew to Boston to sit in Mel Robbins' studio, and somewhere in the middle of their 78-minute conversation she asked the question I haven't been able to put down since.

What do you really want?

She called it one of the most important questions a person can ask, and said most people can't answer it. I believe her, because I've watched it happen in rooms full of women who have every reason to know.

The women who checked every box

Oprah told a story from her talk show years. After tapings, women would come up to her and say they just wanted to be happy. When she asked what would make them happy, they said their kids. When she asked about after the kids moved out, most of them had nothing to say.

In the late '80s and early '90s, she said, women told her they'd done everything they were supposed to. The degree, the marriage, the house, even the good cookware. And it still felt like there had to be more.

That's not a story about people who failed. It's a story about people who succeeded at a list someone else wrote.

The founder version

I know the founder version of that list, because I've spent fifteen years checking it off.

In 2003 I went wedding dress shopping and couldn't find anything built for my body. In 2011 I started Pretty Pear Bride because of it. That grew into Aisle Society, a network of ten publications. I coined a category, inclusive luxury. I bought out my co-founders in 2020 and have run the company on my own ever since. I've written for the LA Times and been covered by the New York Times, the Wall Street Journal, People and Business Insider.

On paper, every box is checked.

And for most of those years, the business lived in my head. Even at Engage, on stage and in the room talking and connecting with people, part of me was still back at my desk. I called that dedication. Looking back, I'd never stopped long enough to ask what I wanted the business to give me.

What I've seen with founders

I've watched this play out with founders I've worked with, too.

Two wedding publication founders came to me thinking they needed more visibility. Once we got past the checklist, the real answer for one of them was community and events. For the other, it was podcasting. Neither of those was on their to-do list when we started. Both were already sitting inside them, waiting for someone to ask a better question.

That's when I started saying it out loud. You don't have a visibility problem. You have a want problem.

When you don't know what you want, every opportunity looks like one you should take, every offer feels like one you should build, and the business grows in every direction except the one that would make you happy.

Three things from the conversation I'm using now

Get still before you ask anyone else. Oprah's point was that the answer isn't on social media and it isn't in your friends' opinions. The moment you're asking everyone what to do is the moment to go somewhere quiet, even if that's a bathroom with the door closed. Your inner voice is always talking. The hard part is getting quiet enough to hear it over everyone else's.

Take the fear out of the question. Mel read a passage from Oprah's book What I Know For Sure about hard decisions. Ask what you'd do if you weren't afraid of making a mistake, being rejected, looking foolish or ending up alone. Take the fear out, and the answer usually gets clear fast.

You're allowed to change your mind. Oprah called the launch of her OWN network one of the biggest mistakes of her life. She woke up in the middle of the night unable to breathe, but she'd already signed and felt she had to keep her word. Mel asked her who she was keeping her word to. Oprah admitted it was the people on the other side of the deal, and that she'd been worried about what they'd think. I think about that every time I look at a plan I committed to before I knew what I wanted.

Where I am with it

When I finally got still and asked myself the question, my answer surprised me. It wasn't a revenue number or a new offer. It was this: I want everyone to live a life doing exactly what they want, with a business that supports it.

Mel said something in that conversation that helped me understand why. Purpose isn't the thing you do. It's what happens in other people when you do it. For fifteen years, I thought my work was publishing. Looking back, the part that mattered was what happened when a bride who'd never seen herself in a magazine finally did, and when a founder stopped chasing visibility and started building the thing she wanted all along.

For me, that looks like evenings with my family and friends instead of evenings at my desk.

That's the business I'm building now. Not a bigger version of the checklist. A life I actually want, and a business that pays for it.

Start with ten minutes

This week, take ten minutes somewhere quiet. Write down what you'd build if nobody needed you to be reasonable about it, and who you'd build it for. Then look at your calendar and count how much of this week points there.

You don't need the whole answer yet. You need to stop living the answer someone else wrote for you.

Every Tuesday I send a short letter about business, life and doing what you actually want. It's one real moment from my week and one question for yours. Join here.