There’s a big difference between dwelling in regret and reflecting on the past: the former keeps us from making progress while the latter can push us to new levels of self-realization and allow us to reflect on the hard-earned wisdom that time has granted us. The upcoming issue of O Magazine features an interesting exercise that allowed Katie Couric, Octavia Spencer, and Oprah Winfrey to do that reflecting by writing letters to their younger selves.

Katie Couric quickly suggests that her old self learn about sports, and Octavia Spencer gave herself advice about direction. But the long, reflective advice of Oprah is a detailed account of the journey from her mindset as an apprehensive black girl to a powerful black woman. Among other things, she tells her younger self to face her past abuse head-on with a heavy dose of faith and self-assurance.

Dear beautiful brown-skinned girl, 

I look into your eyes and see the light and hope of myself. 

In this photo you are just about to turn 20, posing outside the television station where you were recently hired as a reporter. You’re proud of yourself for getting the job, but uncertain you’ll be able to manage all your college classes before 1 and arrive at the station by 1:30 for a full day’s work. Even so, your biggest concern is how to manage your love life with Bubba. Yes, you are dating someone named Bubba. 

On this day you’ve brought him to the station to see where you work, hoping he’ll be proud, too. He seems less than impressed. The truth is, he’s intimidated. You don’t know this, though, because you can see yourself only through his eyes. A lesson you will have to learn again and again: to see yourself with your own eyes, to love yourself from your own heart. 

You’ve spent too many days and years trying to please others and be what they wanted you to be. You will have to learn that the wounds of your past—rape, molestation, whippings for “stepping out of place,” and not being allowed to show anger or cry afterward—damaged your self-esteem. Yet through it all, you’ve held on to a belief in God and God’s belief in you. 

That will be your single greatest gift: knowing there is a power greater than yourself and trusting that Force to guide you. 

The trajectory of your life changed the day you answered the call from Chris Clark, the news director at WLAC-TV. Your response was ignited by the words of your then-favorite Bible verse, Philippians 3:14. “I press toward the mark for the prize of the high calling of God in Christ Jesus.” 

Knowing there is a “high calling” is what will sustain and fulfill you. 

From where I sit now, viewing your journey, there are few regrets. Only months before this picture was taken, you wrote a poem about a “woman becoming.” Even then you understood that success was a process and that moving with the flow of life and not against it would be your greatest achievement. 

Love you deeply, 


This letter both makes me think about how far I’ve come and what advice I would give my younger self. What has been instrumental in your success thus far and what would you change? How have your experiences in the past few years shaped the person you are, and what wisdom would you apply to do things differently?

What would you say to your younger self?

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