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Oprah on the Future of the Oprah Winfrey Leadership Academy for Girls

Every week, Oprah sets an intention exclusively for Oprah Daily Insiders, with reflections on topics like letting go, forgiveness, coming into your own, and more.

Hey, Insiders.

What a week I’ve had. I came to South Africa to deliver a message that I knew wouldn’t be easy for a lot of people to hear.

I know you’ve all made decisions that don’t become easier, even though you know they’re right.

They simply become yours to carry.

For nearly 20 years, the Oprah Winfrey Leadership Academy for Girls has been one of the deepest expressions of my life’s purpose. Thousands of days. Hundreds of young women. Countless moments that changed not only their lives, but mine.

And yet, after years of reflection, conversations, planning, and prayer, I knew it was time for the Academy to evolve from a single residential campus into a scholarship program that could reach even more girls across South Africa.

I knew it was the right decision, but that didn’t make it hurt any less.

One by one, I met with the people who have poured their hearts into this place. Teachers who have devoted decades to nurturing these extraordinary girls.

Administrators who quietly solved a thousand problems no one ever saw. Gardeners who made sure that beauty greets every person who walks the pathways of this incredible campus. (This season, it’s roses.) Housekeepers who cared for the residences as though they were caring for their own homes. Security staff who helped every student feel safe.

And the women in the kitchen. Some of them have been there since the very first day. For 20 years, they have risen before dawn, long before most of the girls stirred from sleep, preparing breakfast, packing lunches, and making sure every meal communicated something deeper than nourishment.

You are cared for. You matter. You belong.

Thanking them was one of the most searing moments I’ve experienced in a long time, because there is no adequate way to thank someone who has quietly given two decades of their life to helping raise other people’s children.

Then came the parents. Many were in tears.

They trusted us with their daughters. They’ve watched them become confident young women with futures that once seemed impossible. Their gratitude filled the room, and so did their fear. Would another school feel like home? Would their daughters continue to flourish?

And then there were the girls. Oh my, was that hard, looking into their hopeful young faces and having to tell the 8th, 9th, and 10th graders that they would soon be transitioning from a campus that has become their home.

As I looked into their faces, I realized something. Change asks every person to grieve something different. The staff grieved a chapter of meaningful work. Parents grieved certainty. The girls grieved familiarity. And I grieved all of it.

We often talk about change as though it’s exciting. Sometimes it is, and sometimes it feels like loss before it feels like possibility.

But every meaningful evolution I’ve ever experienced has asked me to let go of something I loved to make room for something I couldn’t yet see. Leaving Chicago after 25 years of The Oprah Winfrey Show. Starting a network that had no guarantee of succeeding.

Every significant transformation began with the same uncomfortable invitation: Trust what you know, even when your heart wishes things could stay the same.

Leadership has taught me that there is a difference between what is comfortable and what is called for. Comfort would be leaving everything exactly as it is, but calling asked something different. It asked me to think about the next 20 years instead of the last 20. The Academy was never meant to be defined by one campus. It was always meant to be defined by the lives it changed. Now, that mission can reach even farther.

I’ve also learned that when a decision is truly aligned with your deepest values, peace doesn’t always arrive before the decision. Sometimes peace comes only after you have found the courage to make it. I suspect many of you know exactly what I’m talking about. Perhaps you had to leave a marriage that no longer reflected who you were becoming or who you needed to be.

You had to walk away from a career you once loved, sell a family home filled with memories, say goodbye to a parent, or watch a child leave for college.

Those moments rarely feel like victory; they feel hard. Until one day, looking back, you realize that what once felt like an ending was quietly making room for a beginning you couldn’t yet see.

I’ve come to believe that one of the great invitations of life is this: to trust that letting go is not the opposite of love. Sometimes, it is love’s highest expression. It’s about creating the conditions for what can become.

That is the hope I carry for every member of the Academy family.

And perhaps, if you’re standing at the edge of a difficult decision in your own life, it can become your hope, too.

Some decisions break your heart.

The right ones also expand it.

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