If You Could Get a Do-Over, What Would You Do Differently?

Life is full of pivotal moments, choices that shape our paths in ways we may not fully understand at the time. Hindsight often provides clarity, and many of us have at least one decision we wish we could revisit. The concept of a “do-over” is something people frequently contemplate, whether in careers, relationships, or personal growth. Even the most successful individuals, like Oprah Winfrey, have acknowledged moments they wish they had approached differently.

Oprah, a media mogul and one of the most influential figures in television history, has openly reflected on one of her biggest regrets: trying to build a television network while still concluding her long-running talk show. She admitted that attempting to manage both massive undertakings simultaneously was overwhelming and that she should have taken a break before embarking on her next venture. “When you don’t know what to do, do nothing,” she said, emphasizing the importance of pausing and allowing oneself time to reflect before making major decisions.

This lesson is a valuable one. In a society that glorifies constant movement, productivity, and seizing every opportunity, we often fear stillness. The idea of stopping to recalibrate can feel counterintuitive, yet it can be the most beneficial choice. Oprah’s reflection serves as a reminder that success isn’t just about action; it’s also about timing, balance, and listening to our inner voice.

For many, regrets come from rushing into decisions due to external pressures. Whether it’s pursuing a career path that didn’t align with personal passion, staying in an unhealthy relationship too long, or failing to prioritize self-care, these choices often stem from ignoring one’s intuition. Oprah refers to this as the “emotional GPS system”—the internal guidance that tells us when something feels right or wrong. She regrets the times she didn’t trust that instinct, and many of us can likely relate.

Another valuable takeaway from Oprah’s reflection is the idea of leveraging moments wisely. Many people feel pressured to capitalize on momentum, fearing that if they slow down, they’ll lose opportunities. However, taking a break doesn’t mean giving up; it means making space for better, more informed decisions. Instead of rushing into the next big thing, sometimes the best move is to take a step back and reassess.

Regrets aren’t inherently negative; they offer valuable lessons. If given the chance for a do-over, the ideal approach isn’t necessarily to change the past but to apply the wisdom gained from past experiences to future decisions. As Oprah has demonstrated, even the most accomplished individuals have moments of reflection where they recognize what they would do differently. The key is to acknowledge these insights, adjust accordingly, and move forward with greater awareness.

So, if you were given a do-over, what would you change? More importantly, how can you use that lesson to shape your future? The power of reflection isn’t just about rewriting history—it’s about writing a better next chapter.

At 70, Oprah Winfrey Reveals Her ‘1 Regret’ in Life in Raw Interview

Oprah Shares Her ‘1 Regret’ in Life Michael Kovac – Getty Images

Oprah Winfrey opened up about the “one regret” she has about her career.

“I should’ve handled all of that differently,” she said.

Now, she knows making good decisions is all about listening to her “emotional GPS system.”

Even Oprah Winfrey needs a break sometimes—and not giving herself that downtime contributed to the “one regret” she has about her career. She reflected on the memory in an interview about turning 70 in honor of Al Roker’s birthday.

The misstep took hold somewhere between 2008 and 2011, when the Oprah Winfrey Network began and The Oprah Winfrey Show ended—a busy time, as you could probably imagine. “I would not have taken on the responsibility of trying to build a network while still ending the show,” the media mogul told Roker on Today. “That is my one regret. That is my, ‘I should’ve handled all of that differently.’”

She continued: “I’d made a decision that it was time for the show to end, I don’t regret that. What I do regret is trying to do multiple things at the same time.” Instead, Winfrey wishes she would have followed her own advice of: “‘When you don’t know what to do, do nothing. Get still with yourself and do nothing.’ I would have given myself that time,” she said.

It was a hallmark lesson in listening to herself. “Everybody has that natural life force instinct inside yourself that lets you know what’s right or wrong, or that is your emotional GPS system,” she explained. “And any time I’ve ever gone against that, any time, is when I’ve made a mistake.”

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On the flip side, she said, “every time I’ve just gotten still and listened to what my gut said—what that still small voice that resides inside me and you and everybody else says—I would never have made a mistake.”

Aging, after all, comes with the experience needed to follow that “emotional GPS system” that Winfrey referenced, which is why she was excited to turn 70 in February, and why she told Roker not to be scared about hitting the milestone.

“I was excited to make (70),” she said. “I’m excited to make every number. Because I remember many years ago as a young girl, I always thought that I would never make it to the 60s or 70s.” Now, she’s ready for what’s to come. “There is a sense of knowing there isn’t as much time left, and I am at peace with that knowing,” she said. “There’s a sense of urgency for me about living well, living as strongly as I can.”

And hopefully, without any more regrets.