Even someone as wildly successful as Oprah Winfrey has regrets. The billionaire media mogul recently opened up about the one career decision she wishes she could do over. In an interview with author Daniel Pink for his book “The Power of Regret,” Oprah shared a surprisingly relatable mistake that’s haunted her for years. For someone who seems to have made all the right moves in her remarkable career, her biggest regret offers a powerful lesson about listening to your gut and taking time to breathe between life’s biggest moments.
Trying to launch OWN while ending her talk show
Oprah’s biggest career regret was trying to juggle too many major projects at once. Specifically, she wishes she hadn’t tried to launch the Oprah Winfrey Network (OWN) while simultaneously wrapping up her legendary talk show that had run for 25 years. The timing couldn’t have been worse. Instead of giving her full attention to properly concluding one of television’s most influential programs, she was splitting her focus with the monumental task of creating an entire network from scratch. Both projects suffered as a result, with her talk show finale feeling rushed and OWN struggling with low ratings and negative press in its early days.
The pressure to keep moving forward without pause led to what Oprah herself called “101 mistakes” in the launch of OWN. The network faced significant challenges in its early years that might have been avoided with better planning and focus. “I would not have taken on the responsibility of trying to build a network while still ending the show. That is my one regret,” Oprah candidly shared. The initial struggles of OWN became a very public stumbling block for someone who had rarely experienced such visible setbacks in her career. Even someone with Oprah’s resources and team couldn’t successfully manage two such enormous undertakings simultaneously.
Not listening to her inner voice
At the heart of Oprah’s regret was ignoring her own intuition. She admits that a small voice inside was telling her to slow down and take a break, but she pushed it aside. “I didn’t listen to my own inner voice,” she explained in her interview with Daniel Pink. Instead, she “listened to everybody else” who encouraged her to capitalize on her momentum and fame. These outside voices convinced her that taking time off would mean losing relevance or missing opportunities. The pressure to stay in the spotlight and immediately leverage her success from The Oprah Winfrey Show pushed her to make a decision that went against her better judgment.
Oprah has often spoken about the importance of intuition in making decisions, yet in this crucial moment, she failed to follow her own advice. This contradiction wasn’t lost on her. She described this moment as “diverting from listening to the still, small voice that lives inside all of us.” The mistake wasn’t just about poor timing or taking on too much work—it was about betraying her own inner wisdom. Oprah believes this disconnect from her intuition is what led to the struggles that followed. When she looks back at every major mistake in her life, she sees the same pattern: ignoring that gut feeling that was trying to guide her toward a better path.
What she wishes she had done instead
If Oprah could rewrite history, her path forward would have looked completely different. She wishes she had taken a full year off after concluding her talk show—a year to “do nothing” and just be still. This pause would have given her the mental space to process the end of a 25-year chapter in her life and carefully consider what should come next. She needed time to reflect on her accomplishments, recharge her creative energy, and thoughtfully plan her next move. Instead, the rushed transition left her mentally and emotionally stretched thin at a time when both projects demanded her full attention.
The billionaire media mogul now recognizes that sometimes the most productive thing you can do is nothing at all. Taking time to rest isn’t lazy—it’s strategic. “I should have completed one thing, taken a year off, and then decided,” Oprah reflected. This wisdom runs counter to our culture’s obsession with constant productivity and forward movement. Even with all her success and financial freedom, Oprah felt the pressure to keep going without pause. Her regret teaches us that even the most successful people need downtime between major life transitions to make clear-headed decisions about what comes next.
How this haunted her for years
The consequences of this decision have stayed with Oprah for years. In her conversation with Daniel Pink, she revealed that this regret has haunted her for 14 years—essentially the entire time since she ended her talk show in 2011. That’s a long time for someone to carry around regret, especially someone who has achieved so much success in other areas. The struggles with OWN’s launch created unnecessary stress during what should have been a celebration of her talk show’s incredible run. Instead of enjoying the conclusion of that chapter, she was already deep in the challenges of the next one.
The weight of this regret shows how deeply it affected her. Even though OWN eventually found its footing and became successful, those difficult early years left their mark. Oprah described the situation as her “biggest mistake” ever made, showing just how significant this career misstep was in her mind. The public nature of the struggle made it even harder. After decades of almost uninterrupted success, Oprah suddenly faced very public criticism as OWN initially struggled to find its audience. This experience taught her that even with her resources and experience, there are natural limits to what one person can effectively manage at once.
Why transitions need breathing room
Oprah’s experience highlights something many experts know but few of us practice: major life transitions require breathing room. Research shows that successful career changes typically include a “neutral zone” between ending one chapter and beginning another. This in-between time isn’t wasted—it’s when our brains process change and prepare for what’s next. Without this buffer, we carry the mental baggage from our previous role into our new one. We don’t get proper closure on what ended, and we don’t give ourselves the fresh start we need for what’s beginning. This emotional overlap can sabotage even the most promising new ventures.
Think about other major life transitions—moving to a new city, ending a relationship, or starting school. In each case, having time to process the change makes for a healthier transition. Career shifts are no different. By rushing from one major project directly into another, Oprah denied herself the psychological space needed to fully close one chapter before opening another. “Whenever I’ve gone against my gut instinct, I’ve made a mistake,” she explained. The lesson here isn’t just about taking time off—it’s about respecting the natural rhythm of transitions and giving yourself permission to pause before making your next move.
The pressure to keep moving forward
Part of what drove Oprah’s decision was the intense pressure successful people face to constantly achieve more. There’s an unwritten rule in our culture that taking time off means falling behind or losing momentum. This pressure is especially strong for women and minorities who’ve fought hard for their success. Oprah felt she needed to “leverage the moment” and keep building on her fame without pause. The people around her reinforced this idea, encouraging her to strike while her popularity was at its peak rather than taking time to rest and reconsider. This pressure led her to ignore her own instincts in favor of others’ expectations.
We see this same pressure at all career levels. From recent graduates rushing into the first available job to mid-career professionals taking promotions they don’t really want, the fear of gaps on our resumes or moments of apparent inactivity drives many poor decisions. Oprah had enough success and financial security to take a year off without worry, yet still felt she couldn’t pause. If someone with her resources felt this pressure, imagine how strong it is for the rest of us. The lesson here is recognizing when external expectations are drowning out your inner wisdom. Sometimes stepping back isn’t a retreat—it’s the smartest strategic move you can make.
Learning to trust your gut feeling
At its core, Oprah’s regret isn’t just about poor timing—it’s about not trusting her intuition. She knew, deep down, that she needed a break. Her gut was trying to tell her something important, but she let outside voices override it. This pattern is something she’s noticed throughout her life. “Whenever I’ve gone against that gut feeling, that’s when I’ve made the mistakes,” she admitted. Our instincts often pick up on warning signs that our conscious mind overlooks. For Oprah, that internal warning system was flashing red lights about trying to do too much at once, but she ignored the signals.
Learning to trust your instincts takes practice. It means getting quiet enough to hear that inner voice and brave enough to follow it, even when others disagree. Oprah describes this as following “your natural life force instinct.” The irony is that Oprah had built much of her brand around authentic living and following your truth, yet in this crucial moment, she lost touch with her own. It’s a powerful reminder that knowing the right path and actually taking it are two different things. Even those who preach self-trust can struggle to practice it when faced with outside pressure and expectations. The next time your gut sends you a clear message, remember Oprah’s regret before you ignore it.
Giving yourself permission to rest
Perhaps the most important lesson from Oprah’s regret is the value of rest. She specifically said she should have taken a year to “do nothing.” This isn’t about being lazy—it’s about recognizing that periods of rest and reflection are essential parts of a successful life and career. Our brains need downtime to process experiences, integrate lessons, and prepare for what’s next. Constant activity without breaks leads to burnout, poor decisions, and missed opportunities. Yet most of us feel guilty when we’re not being visibly productive. We’ve been conditioned to see rest as weakness and constant hustle as strength.
Oprah’s regret challenges this mindset. Despite her incredible work ethic that helped her rise from poverty to become one of the world’s most successful media figures, she now recognizes that taking time off wouldn’t have derailed her success—it would have enhanced it. Her advice now, after learning this lesson the hard way, would be to “pause, get still” before making major moves. This wisdom applies whether you’re changing jobs, starting a business, or making any major life transition. Give yourself permission to rest between chapters. It’s not just okay to take a break—sometimes it’s the most productive choice you can make.
Oprah’s biggest career regret offers a powerful lesson for all of us. Even the most successful people need time to breathe between major life changes. Listening to your inner voice, even when outside pressure pushes you in another direction, is crucial for making decisions you won’t regret later. Next time you’re facing a big transition, remember Oprah’s wisdom and give yourself the gift of pause before rushing into what’s next.
