For as long as I can remember, my life has been full of contradictions. In college, I split my time between the University of Oregon’s football team and gaming, including serving as a guild master in the online world. Usually, these roles are split between two very different personalities—a 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 don’t 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 Alphabet’s 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 technologist’s 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. I’m 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.
Don’t 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 I’ve 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, I’ve 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 don’t 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, it’s up to you to open the door and let it in.
When you’re a kid, it’s always easier to be on your best behavior when Mom is watching. It’s much more challenging to be well behaved when her attention is focused in another direction. I’ve found this to be true throughout life as well. It’s 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 it’s 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 I’m acting in this moment if it were on display for everyone to see or upon self-reflection several years from now.
Regardless of the eyes on you at any given moment in time, how you treat people always matters. Always be a good person, even when no one is looking.
People talk a lot about the importance of striving for balance in life. For me, it’s much more important to aim for intensity and focus. Wherever I am at any given moment, I try to be fully present in that place and activity. When I move on to the next place, I strive to be equally and fully in that moment. Whether you’re a working parent, a professional, a student-athlete, a home keeper, or anything else that involves multiple facets of life, it’s important to direct your attention. It is through focus that you will be able to fulfill your whole self.
When you’re at work, bring the best version of yourself to the office. When you’re at home, bring the best version of yourself to the dinner table. Don’t shortchange every interaction in your life because your focus is always distributed between everything you have going on all at once. Try to be wholly focused on where you are. Wherever you are, be there right now.
When my wife, Aisha, and I first met with the priest who married us, he told us, “The most important thing you will do at certain points in your marriage is to go for a walk.” As he saw the confusion register on my face, he went on to explain that we wouldn’t always be young lovebirds. We wouldn’t always have the bandwidth to focus the bulk of our time and attention on our relationship.
At some point in our marriage, the priest said, Aisha and I would have a choice: we could either argue with one another or we could go for a walk. On that walk, we could take a moment to breathe, rather than reacting to one another in anger or impatience.
I am not perfect at this, but I always remember the priest’s words when I find myself getting impatient or short-tempered with my wife—or anyone else in my life, for that matter. This lesson has proven to be so important in my own life and marriage that I like to pass on the wisdom I was given by gifting a pair of sneakers as a wedding present. With the shoes, I also include a note that explains what the priest told Aisha and me nearly twenty years ago.
You will lose your patience sometimes. In some moments it will be easier to be empathetic than in others. When you find yourself in one of these more trying situations, take a moment to tie up your sneakers, go for a walk, and take some deep breaths. It will help you get some perspective. The old adage indeed proves true that a happy marriage is made up of two good forgivers.
This is particularly important when it comes to those you love the most. Sometimes it is much easier to be patient and compassionate with strangers than with those we are closest to. Always remember that those who love you the most are the most deserving of the best version of you.
In the pages that follow, I’ll share some of the biggest lessons I’ve learned in my life so far, both personally and professionally. Many of them revolve around these themes of contradiction, serendipity, kindness, whole-self, and patience. Others are downright funny, some are outrageous, and a few are even poignant.
I’ve had the incredible privilege of learning many of the most important lessons in my life from some of today’s most prominent leaders, including Microsoft and Starbucks CEOs Bill Gates and Howard Schultz. I’ve learned some of these lessons in extreme scenarios I’ve been lucky to be a part of. This includes serving as one of the youngest chief information officers (CIOs) of a Fortune 500 company at Starbucks during the company’s turnaround, and sharing stages around the world with some of today’s most prominent business leaders, politicians, and personalities. However, I’ve also learned just as much from lesser-known figures, like my mother and father, and through more run-of-the-mill situations, such as my interactions with my wife and eight kids. The latter have been equally important in shaping who I am and in what I believe and, in many ways, even more powerful.
Hopefully, you will take something away as well. At the very least, I hope you’ll be entertained by some of my greatest victories and foibles, as well as a behind-the-scenes look at some of today’s most innovative and groundbreaking companies and leaders.