This Is What to Consider Before Quitting Your Job: Kara Swisher

After spending about 30 years covering Silicon Valley for The Washington Post and The Wall Street Journal, Kara Swisher decided that she could build something bigger on her own. 

“I thought I could do better,” Swisher told Business Insider’s Dan DeFrancesco during a recent talk with the outlet’s staff.

Swisher went on to launch Recode, the influential technology news site, in 2014. But before becoming a media entrepreneur, she had already built an established reporting career. For example, she helped produce and co-host a conference series for the Journal that became the predecessor to the Code Conference. 

Swisher now co-hosts the Pivot podcast with NYU Stern professor Scott Galloway. She published Burn Book, a 320-page memoir about her encounters with founders and executives in the tech industry, in 2024. She has also amassed two million followers across social media channels.

Swisher told Business Insider staff that she was more comfortable with uncertainty than many of the journalists around her when she chose to build her own business. “I was like, what’s the worst thing? I have to come back? I’m a good reporter. That’s always saleable,” she said. 

Her advice to workers looking to branch out and start their own business is to take an honest look at the downsides before leaving. Deciding to quit can hinge on factors like financial responsibilities and children to support.  

The key to going independent

Swisher said that quitting a job and going independent is not simply a matter of leaving a newsroom or launching a newsletter. It instead requires a point of view strong enough to give an audience a reason to seek out your work rather than another version of what is already available. 

Swisher said she has encouraged media professionals to consider building their own companies when they have a distinctive voice and a real desire to create content. 

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

The most promising founders — in media and other industries — can identify an unmet audience need and deliver work that feels hard to replace.

That customer focus shaped Swisher’s own move into entrepreneurship. When she left traditional media to build her own company, she concentrated on what audiences already wanted. Her core entrepreneurial principle was to start with the user. 

Starting a business isn’t right for everyone

Swisher said that she sometimes tells people to remain in stable jobs rather than force an entrepreneurial path. Building a business requires comfort with uncertainty, she added. 

Swisher said most people can strengthen their entrepreneurial instinct over time. However, she noted that the impulse to take risks was a core part of her personality. 

“I’m sort of restless as a person in general. I always joke, I’m a bad employee. I hate being an employee,” Swisher said. “I’m like, ‘You’re an idiot.’ And I say it, and then it gets me into trouble.”