Oprah's '90s Theme Song Disaster: Why Even Billionaires Have Career Regrets

When you’re as successful as Oprah Winfrey, you’d think every decision you’ve made was brilliant. But that’s not how it works in real life, even for the most accomplished among us. Recently, on the“Baby, This Is Keke Palmer”podcast, Oprah opened up about one of the most cringe-worthy moments of her legendary career: the time she recorded and sang her own talk show theme song in the late 1990s. Called“Run On,”it was a traditional spiritual complete with a church choir backing her vocals. According to Oprah, she was in a moment of uncertainty about whether to keep her show going when she felt a spiritual push to continue. In her excitement about that decision, she decided to make it official by recording her own theme song. It seemed like a good idea at the time. It was not.

Oprah admits now that despite taking singing lessons, she simply cannot sing. The whole thing was what she calls“one of the mistakes”of her career. But here’s where it gets interesting: Whitney Houston, one of the greatest singers of all time, appeared on the show during this era and couldn’t resist gently ribbing Oprah about the song. She’d sing little snippets of it during her guest appearances in 1998 and 1999, a playful nod that clearly stuck with Oprah all these years. What makes this story so worth talking about is that Oprah doesn’t hide from it. She laughs about it. She owns it completely. That’s the kind of confidence that only comes from actually being successful enough that one musical misstep doesn’t define your entire legacy.

The lesson here goes beyond celebrity gossip. When the most powerful woman in talk show history can admit that something she tried didn’t work out, it gives permission to the rest of us to do the same. We live in a world where everyone’s curating their perfect image online. Oprah’s reminding us that even your biggest wins come with some pretty funny failures attached. What’s a career mistake you’ve made that you can laugh about now?