A year ago today I left on a sabbatical from my job at Uber. At the time I genuinely didn’t know if I would be returning or if I would be moving on to something else. I also assumed that if it were something else, that it would be based in San Francisco.
During the break I had a real opportunity to think about life, my priorities and some of the trade-offs I’d been making.
Ultimately I decided to leave Uber. After announcing my departure I was fortunate enough to be offered many amazing roles (understatement) both in the bay area and around the world. But in the end I chose to spend some time advising startups with the goal of helping them avoid the mistakes I’d made in my career and fast-forwarding to the right answer as quickly as possible.
Many people have asked me why I chose not to immediately return to the valley (although I have since been back for a month in January).
First I’d like to clarify that I consider Silicon Valley my second home. I’ve spent most of my career there and most of my independent adult life there. When I first arrived about 10 years ago I immediately felt at home. I never really even felt home sick for Australia.
The reason I’ve chosen to spend some time away though, is multifaceted. There are things that have pushed me AWAY, and things that have drawn me TO other places.
Pushed me away (I list these things not in a mean spirited way - as I said above I still love the Bay Area!):
- It’s wearing to deal with the constant sense that you’re living on a knifes edge. While I was living there I didn’t actually realize that’s how I felt until I spent some time traveling on my sabbatical. It’s like background noise you don’t notice until someone turns it off. At any given time I had to worry about my visa, healthcare, earthquakes, violence in the streets, and increasingly the threat of violence from other countries like North Korea.
- It’s also wearing to see the abject poverty on the streets while walking to work past millionaires and billion dollar company headquarters.
- It’s cold. All the time. Even on warm sunny days if you find yourself in a patch of shade, wrong time of day or in the wrong microclimate you’re not going to be happy.
- Because San Francisco and the bay area attract so many people from out of town, it’s common for your dearest friends to ultimately move away. This can really leave you with a sense of loss and sadness.
- As Trump started winning elections and ultimately won the presidency, I felt a palpable change in both the country and the culture around me. It may have been placebo, but I genuinely felt a jarring gap between my own personal values and the values of the country I was living in. Something I obviously didn’t experience under Obama.
Things that drew me TO other places...
- I missed my family and childhood friends dearly. I missed so many weddings, personal milestones, and tiny moments of shared experiences.
- I found, with my advisory work, the profound freedom to work from anywhere in the world - I can’t be more grateful for this.
- In particular I wanted to spend more time and share more experiences with my brother who is like me in many ways, but also has far more raw talent and potential that I wanted to see flourish
- I wanted to see the world before settling down
- I found that there is now a massive and increasing opportunity to make real impact in other tech hotbeds around the world. China, SE Asia, Europe etc
- I wanted to recharge before starting something new
By far the thing I miss the most by being away is the people. Especially my friends.
Being part of that fraternity is pretty much the longest sustained thing I’ve ever done. You only spend five years in high school. 10 years in the community of Silicon Valley meant that I had found some profoundly amazing relationships with some incredible people.
There’s also a crackling and visceral sense in the Bay Area that the next person you meet could be someone who would change your life or a conversation that would spark the next profound idea.
Just being around these people pushes you to be better, think more broadly and challenge yourself to make a bigger impact.
At the same time, though, many of my cohort have left the Valley to raise families and engage in other opportunities - sadly leaving me with some sense of “you can never go home again”.
I have found the time spent out of the bubble has been immeasurably helpful. Not just for my own well-being but also for my career. It has helped me develop new perspectives and insights that I think will be invaluable for whatever full-time operational role I choose to take next.
In the end, I imagine I’ll come back to the epicenter of innovation and technology. But it probably won’t be before I do a lot more traveling and enjoying my new found perspectives and work/life balance.
Thank you Doriane For taking this photo and reminding me of the occasion with your very sweet words. I dearly miss you too my friend. You’re amazing!
