Stephen Gillett - From Simi Valley to Silicon Valley: A Story of Hard Work, Serendipity, And Questing

For as long as I can remember, my life has been full of contradictions. In college, I split my time between the University of Oregons football team and gaming, including serving as a guild master in the online world. Usually, these roles are split between two very different personalitiesa homecoming athlete and a card - carrying nerd. Rarely do you see them fused into a single person.

I am that person.

This theme has continued throughout my adult life. Early in my professional career, I held technology roles in Silicon Valley venture - capital - backed startups and companies like CNET and Yahoo!. Generally, these techie types are relegated to the back office, where they work on the core information technology services that support the rest of the company. We types are often seen and not heard. Our job is to keep the email and phone systems running, work on building and deploying business applications, and make sure the data center and network dont crash.

I operate under the conviction that, as technologists and leaders, we should be at the very core of business, out in front, using our experience and expertise to challenge the status quo of business and to reshape how organizations compete, innovate, and operate. I remember one particular CNET executive meeting in downtown San Francisco, where it was my turn to present as a newly appointed leader. I had prepared all night long and, when my turn came, I fought through my nerves and managed to stand up and confidently share my update with the captive audience. After the meeting, the CTO pulled me aside to congratulate me on a great session. He also told me, Nobody ever stands up in those meetings. For me, this was a milestone moment during which it was confirmed for me how important it was to follow my own business instincts rather than trying to conform with what everyone else around me was doing.

Throughout my career as a business and technology leader at companies like Starbucks, Best Buy, and Alphabets Chronicle, I stood up many more times. I built and led very successful teams, integrated technology into the core of these companies, and participated in some of the biggest transformations in business today. There were times when my teams played a role in using technology to transform entire markets with technology. But, first, I had to hone the confidence to share the technologists point of view in all aspects of business.

I think it is the athlete in me that has allowed the nerd to step forward. Whereas techie personalities are often happier to work behind the scenes and leave the rest of business to others, in sports you have to possess an acute understanding of your position, expertise, and strengths and weaknesses. Most of all, you have to share all of this to make the entire team stronger. I was able to translate this same mindset into business, which has provided me with the confidence to strengthen the entire team through different thinking, new ideas, and bold innovations.

While my contradictions are extreme, everyone has them. Im sure you do, too. These contradictions might apply to your career, philosophies, point of view, style, or anything else. Sometimes it feels like we should tidy up our contradictions so that we fit more easily into a certain box. My life is a testament to how powerful these contradictions can be if you are willing to accept, get in touch with, and explore them. And, most of all, if you are willing to be proud of them.

You never know where those contradictions might lead you. Mine led me all the way from an average, immigrant - led middle - class household in Simi Valley, California, to some of the most successful companies in Silicon Valley. Not to mention a lot of cool detours along the way.

Dont get me wrong, I still have a lot to learn. But a few things have become clear to me in the course of my forty - three years so far, beginning with the fact that contradictions can be our friend.

As I sit back and think about the lessons that have been most important in my life so far, I can identify a few themes. The pages that follow contain a wide variety of stories from my life, but underlying most of them are these important lessons, which Ive taken with me and attempt to apply moving forward.

Serendipity is no joke. The entire trajectory of my life has been drastically impacted by the simple fact that I was just as polite and helpful to a modest - looking guy who came up to the tech counter at Office Depot as I was to all of the more important - looking , buttoned - up professional types. This seemingly small decision nudged the door open for very important things in my life. Little did I know how powerful that modest - looking guy actually was, and how much he would impact the course of my entire professional life from that point forward.

Because of this and so many other events in my life, Ive learned that serendipity is about much more than just being in the right place at the right time. Far more importantly, it requires a flexible, open mindset and a willingness to take some risk. It is only with this that we can allow unexpected people and circumstances to come into our life and transform it.

You can try to map out every minute detail of your life, which might get you from Point A to Point B. But, in the process of sticking to a rigidly structured map, you may very well miss out on detours you dont even know exist; in gaming we call these side quests. Often, it is along these unanticipated detours that the most profound and unexpected joy and growth await. The most profound things can happen when you are willing to put yourself in situations that allow room for serendipity to do its thing. This might include everything from meeting someone special to signing up for a new challenge at work. Most of the important things in life require a certain amount of effort on your part, but they also involve an undeniable element of alchemy.

Stay open. You know what they say: when you hear opportunity knock, its up to you to open the door and let it in.

When youre a kid, its always easier to be on your best behavior when Mom is watching. Its much more challenging to be well behaved when her attention is focused in another direction. Ive found this to be true throughout life as well. Its easy to treat others with integrity and respect when people are watching. There is a direct benefit to you in doing so. More effort is required when everyone is looking in another direction.

Whether its family, friends, coworkers, or complete strangers, I always try to stay in the moment and be aware of how I am treating others. The more stressed out or short on time I am, the more important this becomes. In the midst of my daily interactions, I make a point of asking myself if I would be proud of how Im acting in this moment if it were on display for everyone to see or upon self - reflection several years from now.