Put Your Head Down For Five Years, And Then Look Up

Back on August 15, 2011, I emailed my friend Joel with an idea, part out of excitement, part out of frustration. I think about it every August. Last year, I wrote about it here. For me, mid-August is like the beginning of the year, because I can point back to it as when it began for me. In 2014, some things were changing, but most of them were the same. A year later, almost everything has changed. I am in a new place in the Valley. I have much fewer work arrangements, but those now are much deeper. I will be making fewer investments, but will put more wood behind those arrows. I will have less free time, so I will have to be more protective over how I spend my time.

That summer and leading into August 2011 was rock-bottom for me. Now, four years later, nothing is settled yet, but I am in a better place and with each passing day, I gain more clarity over what I want to do next. Maybe it is just one elongated refinement of an idea that will eventually sharpen into one that makes sense and, more importantly, fits — not by being an interlocking part — but by slicing in.

I grew up working in and around restaurants. I had many jobs as a busy boy, dishwasher, line cook. I remember in one of my roles, the sous chef was a great guy but also a hard ass, he drove everyone really hard. One day after work, as we would often all go get a drink, I recall him telling me about when he started out as a cook and how hard it was for him (without formal training) to go from a dishwasher all the way up to sous chef. He worked in very competitive kitchens. He said that he used to have a boss in the kitchen who would tell everyone during their first days on the job: “Put your head down for five years, and then look up to see where you are.”

I haven’t put my head down over the past four years, as I’ve used my blog and online networks to share ideas and learn about industries I have no former experience with, but in figurative terms, I have put my head down, worked at startups, help run deals, helped hire people, helped others raise money, helped others guide to exit, and so on and on. It feels good to just be helpful, if even an ounce helpful, and it’s a great way to bootstrap learning. I’ll likely put my head down more this next year. And, then, I will hit five years, and then, I will really look up and see what is all around me. The magical part of about the Bay Area is that fortunes can change quickly. A lot can happen in a year. And sometimes, there’s only one direction to go.