Media mogul Kara Swisher shares advice on when to quit your corporate job and go solo

Some people dream about breaking free and building something of their own.

The big question is: When’s the right time to take the leap?

For starters, you might be feeling disenchanted with your current role.

“I thought I could do better,” Kara Swisher told Business Insider’s Dan DeFrancesco during a talk she gave to newsroom staff.

Before launching the media brand Recode, Swisher made a name for herself as a reporter at The Washington Post and The Wall Street Journal, eventually coproducing and cohosting The Journal’s “D: All Things Digital” conference series, which later became Code Conference.

When Swisher eventually went independent, she said her risk tolerance was greater than that of many of her journalist peers.

“I was like, what’s the worst thing? I have to come back? I’m a good reporter. That’s always saleable,” said Swisher, who cohosts the “Pivot” podcast with Scott Galloway, and is the author of “Burn Book.”

Swisher said anyone considering going out on their own should assess their risk profile. Financial obligations, children, and the need for reliable healthcare can play a role in deciding to take a leap.

Swisher, who has given guidance to other media professionals who want to start their own ventures, said that having your own voice is another critical component. When she branched out on her own, Swisher said she was focused on the audience, what consumers wanted, and what they had not yet realized they needed. She said she’s urged others with a strong individual voice to similarly pursue their own venture.

“You can tell when people really have something to say and want to make something,” Swisher said.

Don Lemon, for example, has thrived since going independent, she said. Lemon departed from CNN in 2023 after 17 years at the network. He has since worked as an independent content creator, sharing his work on social media and hosting live events.

Building a business also requires an entrepreneurial mindset and a willingness to make trade-offs, even if that means something like taking the subway home instead of relying on an Uber every night, Swisher said.

Not everyone has that mindset, Swisher said, and she sometimes advises people to stay where they are. However, she said she believes people can develop that muscle, and that there’s more room in the current media climate for experimentation, whether through subscriptions or nonprofit newsrooms. Even if you don’t have a large audience, you can do well if you develop a loyal base, she said.

“Most people actually can be entrepreneurial,” Swisher said.