I went on to hold several other roles, which have all been challenging in different ways.

In the summer of 1996, after spending 20 years in the magazine publishing business, I was unsure about what my next career adventure should be. I had built a solid track record at such great brands as Family Circle, Ladies’ Home Journal, New York magazine and Adweek, but all of a sudden I was unsure that I wanted to be a magazine publisher for the next 20 years.

Not long before that, I had invested in and joined as president a company called Standard Rate & Data Service to have the experience of turning around a company and either selling it or taking it public. It also gave me the chance to sit on a Board for the first time. We successfully put the company back on solid footing and sold it after 18 months (for four times what we paid for it!).

I was thinking about what was next when a friend who ran a major advertising agency called and told me about a new media venture he was helping to finance. He asked me if I’d meet the founder and CEO and take a look at the company to see what I thought of its prospects, suggesting that I might be interested in joining.

After listening to him describe the idea, I said I just didn’t think it sounded right for me. “I’m too old for this ‘new media stuff,’” I said. “I’d be overdressed for it. And I don’t think I’d work well with geeks.”

Though I was half-joking, I thought that a technology-driven company would be beyond my skills and too far outside my comfort zone. My friend convinced me to take the meeting anyway.

We set it for 45 minutes but it turned into three hours of conversation, most of which I didn’t completely understand, as the founder was an engineer and I was “all media all the time.” Turns out he didn’t understand most of what I was talking about either, but we both knew that if his vision was to come alive, someone had to be able to translate the technology’s capabilities for potential advertisers.

With trepidation but a great deal of excitement, I leaned in to the opportunity to be a digital media pioneer and became executive vice president of DoubleClick. In its first five years, we built the company into a “new media” powerhouse with 3,200 employees in 23 countries and generated half a billion dollars in revenue.

I went on to hold several other roles, which have all been challenging in different ways. It has been 18 years since I held my nose and jumped into the uncharted waters of digital media. Where would I be now if I hadn’t leaned in?