Briefly Reflecting On The Last Year

With 2018 winding down, I’ve finally gotten some downtime to digest the big changes I’ve personally undergone this year. They’re all good changes. After years of having pretty bad luck, I feel as if I have gotten a bit too lucky. Today is the day I begin to write my annual “Reflecting On 2018” post for tech, startups, and VC — but I don’t think I can get my mind in a place to do that work until I clear my brain first.

This year, our family (and me personally) went through some foundational changes. On the work front, I had the opportunity to join Lightspeed as a venture partner; and with Haystack, the seed fund I launched in 2013, Haystack finally recruited incredible help to come onboard, Haystack became slightly more institutional in nature (including fund infrastructure, leading deals selectively, etc.) and Haystack began to lay the foundation for a larger, more complex enterprise in the future (stay tuned).

But 2018 for me was also defined largely by personal decisions for myself and our family. With our eldest kid entering kindergarten, we searched around the Bay Area for a place to put down roots. For the past few years, I wasn’t sure I would have a career, or if we could stay in the Bay Area. When I moved to Palo Alto in 2011, I had no idea how the region and tech overall would transform into what it is today. Back then, we all didn’t realize the stakes.

While I knew selecting a new “hometown” was an important decision, I didn’t anticipate how hard it would be, and also how much of a responsibility it was. I was fortunate to be raised within one school system. I know folks will always say, “but kids are resilient” in response to moves, and I’m sure they are, but I wanted to see if we could plant them in one place. We all had to make sacrifices with this move. It took about a year’s worth of time for me to obsess over all the angles.

Now with our 3 kids in school — the two little twins are in nursery school, while my daughter started Kinder — I feel like this is an incredible gift we’ve been able to give them. It pales in comparison to what mothers have to go through, the physical stress, the sacrifice — but I feel grateful for the opportunity many others have shown to me to make this possible for my children. It is a huge reason why many of us obsess over work, why we pour everything into what we do. After a good year of planning the move, I am rewarded with the pleasure of walking my daughter to school almost every day of the week. We bump into other kids across grades on the stroll through the neighborhood to the school. Sometimes, she wants me to stay an extra second after the bell rings; other times, she runs into a buddy on the playground and waves at me that “she’s good” and I can go early. With so much of our collective work inputs driven by luck (which is derived from sacrifice and hard work), this new little morning tradition I have now in 2018 feels like the luckiest output in the world.

Now that I’ve written this and begun to clear my head, expect more writing here from me, over this holiday and into next year. With all the big work and life changes last year, I didn’t get to write as much as I would’ve liked to or need to. If I don’t write about my environment, I find that I don’t learn as quickly and that my brain gets clogged. So I’m looking forward to the next few weeks of writing and reflecting, and to prepare for what will likely be a very unpredictable 2019.