Oprah Winfrey Reveals How People-Pleasing Led to Her Worst Career Year

Oprah Winfrey revealed that the year 2012 marked one of the worst periods of her life, driven by a career decision she made despite knowing it was wrong. Winfrey launched the Oprah Winfrey Network in January 2011, just months before her landmark talk show ended its 25-year run in May 2011. The network suffered from low ratings immediately, culminating in 30 staff layoffs in March 2012. Media headlines continuously targeted the venture. “Every single story headline about me was ‘Oprah and the struggling OW Network. Oprah and the struggling OW Network,'” Winfrey said on the podcast. “And it was hurtful and painful to me because it was the truth. I was struggling.”

The Cost of Ignoring Intuition

Winfrey stated that she experienced intense physical stress because she ignored her inner voice, which was so strong that it woke her up at night unable to breathe. She explained that she pushed forward with the network agreement not out of true desire, but to avoid disappointing the parties involved on the other side of the deal.

I was keeping my word because I was trying to please the people on the other side. I was thinking, ‘What are they going to think of me for changing my mind?’ Winfrey said on the podcast.

She compared the situation to walking down the aisle for a wedding and realizing the marriage is a mistake. Even when invitations are sent and guests are waiting, she noted, individuals still retain the right to walk away.

Ownership Shifts and Later Reflections

The network was originally established as a joint venture between Winfrey’s production company, Harpo, and Discovery. Over subsequent years, Discovery increased its stake in the cable channel significantly.

In 2017, Discovery paid $70 million to acquire an additional 24.5% stake from Harpo, pushing its ownership past 70%. By 2020, according to reports from The Hollywood Reporter, Winfrey exchanged most of Harpo’s remaining stake for Discovery shares valued at more than $35 million. That transaction brought Discovery’s ownership up to 95%, leaving Harpo with a 5% stake.

Reflecting on the timing of the venture in a 2024 interview with Al Roker on the Today show, Winfrey identified the launch schedule as her primary professional regret. I would not have taken on the responsibility of trying to build a network while still ending the show, she said in that interview. That is my one regret. That is my, ‘I should’ve handled all of that differently.’