From CIA to Google to Entrepreneur: How Saying 'Sure, I'll Try It' Transformed My Career

Candice Bryant's career journey is a testament to the power of saying 'yes' to unexpected opportunities. Starting at the CIA in her 20s, moving to Google in her 30s, and becoming an entrepreneur in her 40s, she shares the philosophy that guided her through each transition.

The Power of 'Sure, I'll Try It'

Bryant's career began with a chance encounter at a career fair. Despite having no professional clothes, she attended and applied for a full-time job at the Central Intelligence Agency after a recruiter suggested it. She started at age 21, launching a 16-year career as a political analyst.

'My whole career has really been a series of 'Sure, I'll try it' moments.'

Lessons from the CIA

At the CIA, Bryant learned how fragile the world can be and how decision-makers often act with incomplete information. In 2018, she moved into a communications role, drawn to the challenge of working in communications at an organization known for secrecy.

Making the Leap to Google

In September 2021, Bryant joined Google as an internal communications manager. She worked on the company's response to the COVID-19 pandemic and later moved to the Search organization during the generative AI boom. She collaborated with brilliant engineers to translate their work for broader audiences.

Why She Left Google

Bryant realized that powerful technology nobody understands won't transform anything. She saw a gap between Silicon Valley and everyone else, and felt she could have a bigger impact helping people understand AI from outside Google. In October 2025, she left to pursue entrepreneurship.

Becoming an Entrepreneur in Her 40s

Today, Bryant focuses on advisory projects, angel investing, a weekly AI newsletter, and building AI-related products. She launched an app called Cello that provides daily prompts to explore practical uses of AI. Her mission: making technology accessible to everyday people.

'Building from inside an established brand is easier than building on your own, but what you build on your own is yours.'

Follow Opportunities, Not a Set Path

Bryant advises against feeling pressured to follow a single career path. Entrepreneurship may only make sense during a certain phase of life. She started investing in real estate in 2010 to give her future self more freedom. Her key takeaway: just because something doesn't make sense today doesn't mean it won't later.