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Ideas in the Wild: How Serendipity Took Stephen Gillett from Office Depot Employee to Fortune 500 CIO

To succeed in business and in life, you must be focused and committed. But it also takes serendipity to be successful, which means more than being in the right place at the right time. It’s about being flexible enough to allow unexpected things to enter and transform your life. Stephen Gillett went from part-time technology […]


To succeed in business and in life, you must be focused and committed. But it also takes serendipity to be successful, which means more than being in the right place at the right time. It’s about being flexible enough to allow unexpected things to enter and transform your life.

Stephen Gillett went from part-time technology specialist at an Office Depot to one of the youngest CIOs of a Fortune 500 company by keeping himself fully present and open to all possibilities. In From Simi Valley to Silicon Valley: A Story of Hard Work, Serendipity, and Questing, he shares his journey and the lessons he learned while working with Bill Gates, Starbucks’ Howard Schultz, and a host of other influential innovators.

I sat down with Stephen to find out what made him want to write the book, his favorite actionable idea he shares with readers, and how he’s implemented that idea in his life.


What happened that made you decide to write the book? What was the exact moment when you realized these ideas needed to get out there?

I am married to my high-school sweetheart and we have eight wonderful children. When I began to consider how best to capture an unexpected life full of enriching experiences and the ups and downs along the way, I decided that writing a book was the best path available to me. It was originally intended as a sort of time-capsule to capture these lessons and experiences for my children as they grow up and have lives and families of their own.

When others started to read the early manuscripts, I was encouraged to make the book more broadly available and share these experiences and lessons with a larger audience… so here we are. The book captures the serendipity I’ve experienced, where unexpected early situations yielded influences that shaped me for the next twenty years.

I’ve had the chance to work with some of the most influential business leaders of our time, all of whom taught me lessons on how to — and how not to — act as a leader. The book weaves in and out of all aspects of my life, from the son of an immigrant from the Middle East to a modern CEO in Silicon Valley. It is a tribute to the first forty-three years of my life, packaged up as a gift for my family and others to explore and take from in a way that is meaningful to them.

What’s your favorite specific, actionable idea in the book?

My favorite idea is the concept that you need to put yourself in the position for serendipity, or something unexpected to happen. Early in the book I talk about working at Office Depot as a junior retail analyst and the sequence of events that led me to that job put me unexpectedly in a position that would shape the next twenty years into something extraordinary.

I also shared about having the confidence to be bold, take risks, and show grit in the face of life’s biggest adversities. I love the notion of being a good person, even when nobody’s looking. I discuss the importance of being aware of those around you and helping them in the ways that you were helped. I know that’s more than one, but all these ideas are game-changers!

What’s a story of how you’ve applied this lesson in your own life? What has this lesson done for you?

I’ve tried to do the unexpected, whether it was taking a job at a company that everyone thought was about to go out of business, moving across the country, or quitting a promising athletic team to get a job working in tech. All of these lessons can be summed up by charting your own path, taking risks, having grit, and putting yourself in unexpected situations. More often than not, good things happened, but great adversity also came. How do you ride the waves of your own life, and when you fall off the proverbial surfboard, start paddling and get yourself up and back in the game. That’s what I’ve learned in my journey, and that’s what I share in the book.

For more advice on being open to serendipity in your life, you can find From Simi Valley to Silicon Valley: A Story of Hard Work, Serendipity, and Questing on Amazon.

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