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Oprah Revealed Her Biggest Regret. It’s an Essential Lesson for Anyone Who Wants to Change Their Life

Jessica Stillman

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For his book the Power of Regret, best-selling author Daniel Pink surveyed more than 20,000 people about their biggest regrets. I am sure he heard some interesting and heart-rending stories. But recently he added one more truly fascinating example to his collection of missed chances and bad decisions — the deepest regret of Oprah Winfrey.

The media mogul’s confession isn’t just interesting as a bit of celebrity self-revelation. It turns out her biggest regret contains an important bit of wisdom anyone thinking of making a big life change needs to remember.

Even billionaire moguls have regrets

When Winfrey interviewed Pink for The Oprah Podcast (check out the whole episode below if you’re interested), most of the conversation was centered on the main thrust of Pink’s book: how to leverage regret to improve your life. But near the end of the podcast, the discussion veered into more personal territory.

“My deepest, deepest regret is that I didn’t take the time when I ended The Oprah Show before I started the next thing,” Oprah reveals.

Why has not taking a breather after ending one phase of her life and starting another haunted her for 14 years?

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Jessica Stillman
Jessica Stillman

Written by Jessica Stillman

Top Inc.com columnist/ Editor/ Ghostwriter. Book lover. Travel fiend. Nap enthusiast. https://jessicastillman.com/

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