If I Hadn't Passed Up a Job at Apple, I May Never Have Landed at eBay

In this series, professionals reflect on their inevitable career mistakes. Follow the stories here and write your own (please include #BestMistake in your post).

It’s often said that you never regret the things you’ve done; you regret the things you didn’t do when you had the chance.

I can relate. In 1998 I was leaving my job at Bay Networks, and I was approached to be part of the founding team of drugstore.com. I believed it was a big idea and I believed in the people, but my family didn’t want to move to Seattle. So, instead, I took a job as the CIO of Gateway in San Diego. It was a great job, but over the next year I couldn’t help but watch drugstore.com’s meteoric rise. The company went public in 1999.

“Oh man, I would have made a fortune!” I thought. "Did I make a mistake?"

But mostly, I stayed focused on what I was doing. I didn’t think too much about the decision. Maybe I should have — because it happened again. A few months later, I got a call from Apple. The company was looking for a CIO. I didn’t want to make a lateral move. And, the company wasn’t doing that well. Steve Jobs had just come back, but the stock crashed when the tech bubble burst and the company warned that quarterly estimates would fall short of expectations. “We've clearly hit a speed bump,” Jobs told investors. I wasn’t interested. “Thank you, but no thank you,” I told them.

Now, of course, we all know that valued at $700 billion, Apple is the most profitable company on the planet. It’s also one of the most exciting. It would have been quite a ride, and my net worth would have been significantly altered. Was thinking Apple was not worth my time a mistake?

Yes, I have regrets. But I never forgot the Apple error. As the philosopher George Santayana famously said, “Those who cannot remember the past are condemned to repeat it.” And from the Apple experience came the next opportunity — one I knew to consider, and soon took.

Not long after ignoring the call from Apple, a little company called eBay called. They were in a big, ugly, gnarly situation. They wanted me to become head of technology and instead of seeing this move as a risk, I saw it as an opportunity. I thought the company had great prospects and I wanted to help them achieve it. Truthfully, it probably helped that Meg Whitman approached my wife directly and won her support, which also won mine.

Everyone else thought going to eBay was a crazy decision. But from the moment I started, I loved working there, and eBay turned out to be quite a rocket ship. Not just the stock, or what I earned, but the opportunity to change the trajectory of a company, reinvent an industry and enjoy the interesting new orbit it set me on.

I never again looked back.

For too many, life is full of regrets about choices we should have made. But truly, that’s such a waste and so counterproductive. The most important thing is to make a decision and then figure out how to make that decision work. Successful people never look backwards with regret. They always look forward. After all it’s hard to run as fast as possible when you are looking at what’s behind you, or even when you’re focused on looking left and right at what else is around you. The best mistake I made wasn’t in leaving those jobs behind; it was in letting them go so I could focus on looking ahead. That’s always the only way we really advance in what we set out to do.