Oprah Winfrey talks about the only decision she regrets in her career.

In a conversation with Al Roker on Today, Winfrey, 70, reflected on their successes and failures throughout their lives as they discussed Roker’s 70th birthday. The Oprah Winfrey Show ended in 2011, the presenter admitted that she wished she hadn’t immediately thrown herself into another project.

“I wouldn’t have taken on the responsibility of building a network (OWN) and ending the show at the same time. That’s my only regret,” she said. “I think I should have handled it all differently. I should have finished one thing, done nothing for a year and then decided what was next for me.”

She continued, “I had decided it was time to end the show, and I don’t regret that. What I do regret is that I tried to do several things at once. I would have done what I tell everyone else: ‘If you don’t know what to do, don’t do anything. Be very quiet and do nothing.’ I would have taken that time.”

Winfrey explained that since the end of her show brought so much attention to her, she felt pressured by those around her to “seize this moment” to create something new. After 29 seasons, she said, she wanted “a break.”

“Everyone has this natural instinct in them that tells them what is right or wrong, or that’s their emotional GPS system, and every time I’ve ever gone against that, I’ve made a mistake,” Winfrey confessed. “Every time I’ve just gotten quiet and listened to my gut – what that little voice inside me and you and everybody else is saying – I would never have made a mistake.”

Today, Winfrey values ​​her downtime and relaxation more than anything else. The simple things, she says, bring her the most joy.

“When it rains, I love life. You know why? No expectations,” she said. “Nobody expects you to go out on a rainy day. When the sun shines, everyone says, ‘Come on, let’s do this.’ I love a rainy day. A rainy day, a fireplace, a blanket and a dog at your feet and a great book? That’s it. That’s everything to me.”

Never miss a story — sign up for PEOPLE’s free daily newsletter to stay up-to-date on the best of what PEOPLE has to offer, from celebrity news to compelling human interest stories.

When Roker asked if she thought she would be the same person if her show had started now rather than in 1986, Winfrey quickly replied “no.” She explained that she was proud that she was able to address issues that people would not have been able to talk about freely without her show.

“It was a different time,” she said. “I often think about it, also in relation to The Oprah Show and the immense range of topics we covered on a daily basis. We just talked in a real and meaningful way about what was going on in people’s lives. Raising children, overcoming cancer, leaving abuse behind. Every single imaginable dysfunction in our culture that The Oprah Winfrey Show was able to address it in a way that allowed people to see the best in themselves and realize the possibilities of what could be.”

“I just spoke in Grand Rapids and someone said, ‘You changed my life because you showed me what I can be and what I need to be,’ which is really a great testament to what a television platform can do,” she added.