Jacki Kelley

CEO

Location: New York, NY

"In the silence it hit me that if I did not do this I would wonder my whole life if I gave up to soon."

In 2005 I celebrated my 17th anniversary with USA TODAY. I had joined the company as an intern in my last year in college and 17 years later I had enjoyed nine exciting roles, worked in two divisions across domestic and international editions, and experienced some of the most joyous and transforming experiences with this team.

That summer, I had a special lunch on the Pier in Cannes with Wenda Millard – at that time the Chief Revenue Officer at Yahoo! -- who had an idea for a role that would leverage the travel experience I had for much of my time at the paper. While I knew it was critical to get deeper digital experience I had no idea if I could be successful in a new company. And to make the stakes higher, I had to relocate my family from a community we loved in Virginia to the chaos of New York, accept a much smaller role, reduce my income and move from managing a global advertising team to being an individual contributor.

I remember the afternoon I made the decision to say yes. As a family we agreed that it was my decision; either way, we would make it work. I went to the basement and sat on the floor in complete silence. In the silence it hit me that if I did not do this I would wonder my whole life if I gave up to soon. Heaven forbid, I settled. Ironically, I could envision my life if I did not change anything—it was the unknown that called me. If there was ever a time to lean in, this was it!

I left Yahoo! eighteen months later as the head of Worldwide Strategies & Solutions (no longer an individual contributor!) but more importantly left with the confidence that I could indeed leap into the deep end, seek to understand, learn, gain influence and construct a new chapter. I have worked at two companies since then taking an even more dramatic leap in 2009 to leave the sales ranks to run a media agency. There is no doubt if I had not taken that first step, I never would have had the opportunity or the courage to make the decisions I have since.

There is always someone that will believe in you in a way that you don’t believe in yourself.   Hear them. There will be opportunities that feel too big, too small, and too hard; find a quiet place, listen to your aspirations and don’t be afraid to leap. Not trying is wondering your whole life if you gave up too soon.