Connecting the dots
Exactly 5 years ago, this week, I arrived in San Francisco. It was the first time I’d been to the Bay Area, California or basically anywhere west of Hamilton, Ontario.
I was there for a job interview, but it felt more like a pilgrimage. For the last decade — my high school and university years — I’d been deeply inspired and influenced by this 50-mile spit of land. Early on, it was the magic that was Steve Jobs’ Apple. Later, the culture-shifting influence of companies like Twitter and Facebook, as well as hundreds of little startups surrounding them. I took Apple’s annual keynotes as seriously as football fans take the Super Bowl, skipping school to watch them live. I consumed every talk, interview or podcast I could find featuring startup founders, software designers and programmers. At that point, I hadn’t met others who shared the same passion, but I had a feeling San Francisco would be a place I could meet a few.
At this point, in the fall of 2011, I was also a year and a half into the most beautiful relationship of my life with my partner, Clare. She was just about to go back to school and would be stationed in Ontario for another few years. So, while this opportunity in San Francisco seemed enticing, my visit to the Bay was motivated more by curiosity rather than a serious plan to move away from her.
I landed and had an interview on my first day in the city, and returned to my hostel to learn about some tragic news: Steve Jobs, after his long fight with cancer, had passed away. My long-time hero, a man I’d built up in my head to seem immortal, was gone forever. I was deeply saddened. I had always dreamt that I would one day watch a Jobs keynote live, maybe even meet the man. But I had let that dream be just a dream for too long and now it was too late.
Clare and I spoke that night and I told her how regretful I felt that I hadn’t taken the chance to come out here earlier. I told her that I felt like the Bay was calling to me — I had to be here. So, together, we decided to take on the challenges that come with a long-distance relationship in hopes of pursuing our dreams — for her, a Midwifery degree and for me, a chance to hone my craft; designing technology around the people that understood it best.
I moved to the Mission a month later and the next four years proved to be the wildest ride of my life. I met some wonderful human beings who became my closest friends and collaborators. I learned that technology is as much about philosophy as it is about science. I got in with an ambitious bunch of people who set out to bring the world’s best education to everyone. I conquered bay area hills on my bike and reached my athletic peak. I even managed to ruin Valentine’s Day for everyone and then have Verizon make a commercial about it.
This period allowed me to discover the kind of work that kept me up at night and got me up in the morning. It let me realize what I was good at and how I wanted to contribute it to society. I developed a strong work-ethic. I saw what could be possible when people come together, put egos aside and strive towards a virtuous vision.
Last year I traded my long-distance relationship for a remote gig. I’d feared that leaving the Bay would be a step backwards in my career — it’s been anything but! I’m more excited about what I’m working on now than ever before. I’ve been challenged in ways that have accelerated my growth beyond anything I’d thought possible. My life/work/play/health balance has never been better and I’m more inspired than I’ve been in a long time.
Steve used to say you can’t connect the dots looking forward; you can only connect them looking backwards. Looking back, I see patterns in what’s possible when you manifest your hopes and dreams, even (actually, especially) when you have to sacrifice so much to reach them. I hope the next five years will be filled with even more risks and rewards. I hope to continue following my heart, my gut and my curiosity.
