Published Date: May 12, 2012

I get asked from time to time whether I regret leaving Zillow in early 2010. I’ve even been called crazy over the decision. In fact, the reason I’m writing this post now is that it just happened again two days ago by a total stranger on an island tour in El Nido (whether I regret it, not that I’m crazy). After all, marketing for Zillow was the job everyone wanted for a well funded tech startup. The team was as good as they come, following a grand vision tackling an industry sorely in need of a wake up call in terms of the consumer web. I was making good money. I truly truly loved my job.

Why’d I leave then? In short, I got bored. I got complacent. Staying at Zillow would have been the “easy” road to follow. You know, the path everyone expected me to take. Sure, there would have been a few challenges along the way, but it wouldn’t have stretched me to my limits. As a company grows, every employee gets more and more defined in their area of specialty. I got to a point where I felt like I could do my primary job (which was link building and social media) in my sleep. But focusing and getting good at one — or two or even three things — isn’t enough for me. Anyone that I’ve worked with can attest to the fact that my mind races a million miles an hour with ideas (hence the reason exists). I need to be constantly exploring new opportunities and evaluating strategic options to keep my mind stimulated. Always an entrepreneur, spending several years climbing the corporate ladder wasn’t my idea of fun. I wanted a new challenge. And I wanted to see more of the world.

Would I be better off financially had I stayed the course? Hell freaking yes. Heck, if I was still there, in another year or so, I’d all but be guaranteed to be a millionaire if the stock price continues its current trend up and to the right. But, if I’m certain of one thing, it’s that money doesn’t buy happiness.

I’ll admit, there are some aspects of my life I’d change were I given a mulligan. But, do I regret my decision? The answer on this career decision, the largest I’ve ever made, is a resounding no. Not for a second. Had I had stayed at Zillow — I would have missed a wide range of experiences that has shaped who I am today. The best summer of my life living on Santorini. Seeing Rocky’s orphanage in Kenya. A first hand look at microfinance in rural Ghana. A summer in Saint Thomas. Living in Chiang Mai for 2 months and meeting some amazing people.

It’s not worth living a life of regrets.