Planning And Strategery Over The Holidays

The end of the year and holidays in general are, at least for me, a time to plan out the next year. Sure, as Mike Tyson mused, everyone has a plan until they’re punched in the face, but even if that punch is coming, having the time and space to let my brain rest a bit and mill around the house (even with kids and their chaos) let’s me think about what I want to focus on the next year and what I want to eliminate. I’m sure many of you reading this do some version of the same. It’s really the only time of year in the startup and investing world left.

Some folks entirely unplug in the evening, more do it for the weekends and even in the holidays. I find that hard to do, personally. In many ways, work/email has eaten into the evening-share minutes at home. But, most of us love what we do, and others around us do the same. That’s an old story. Weekends can be more sacred time, as Fred Wilson wrote about it earlier this year; I still do a ton of work on the weekends (doesn’t feel like work) because it’s the only quiet time I have during the week. Then there are holidays where folks go entirely off the grid, as Brad Feld has written about taking digital sabbaths. I hope to reach for these later in my career, but they feel far away right now with little kids and unproven funds.

The reason I like this time of year and the 2-3 week slow down is that it’s a real break from meetings. While I love what I do, it is a people-intensive, meeting-intensive business. I am a people-person (whatever that means), and I like meeting a variety of old and new faces each week. But meetings can generate some unwanted follow-ups, or just space in your brain. Each year at this time, I tell myself I will be more judicious with my time. And once Labor Day hits, schedules devolve into a mess.

What I do now is literally print out a 12-page calendar and start blocking off time. On Mondays, I am down on Sand Hill at the Lightspeed partner meetings; on Fridays, I am holed up in my home office taking no calls or meetings. From Tuesday to Friday, I walk my daughter to school. I’ll try and budget one evening per week for meeting friends or a work event and try to stick to it. I’ve already said “no” to a bunch of events or dinners for Q1 of 2019. I then hand this calendar to my EA to help set boundaries in my schedule, and ask my colleagues to always speak up if they see me lurching over my stated goals.

I’m going to try and write every day here — I have a backlog of topics I jotted down in 2018 but didn’t have time to think through. For the first time, I am entertaining the idea of getting office space — but I probably won’t. For the first time, we may actually brave the elements and take a family vacation via road trip, as our kids’ school breaks line up. I am going to preserve energy in the summer for the fall, which is always crazier I anticipate it to be. In terms of available hours, I am already in a finite territory, and that feels good — to leave those hours open for meeting new founders, and having the best opportunities compete for those limited slots.

Of course, there’s always a potential “punch in the face” coming. But, we cannot control such things, we can only be prepared for them if they arise, and my preparation is (hoping to) play offense with my time and attention in 2019. My kids are slowly growing up (and taking up more time), and the portfolio from earlier funds are maturing, and I’ve only known an incredible bull market driven by technology since I moved back to California in 2011. Now, looking ahead, I have to expect some cyclicality to be factored into the equation. That’s a topic I’ll muse on tomorrow…