We’d barely made our first venture investment when I tattooed Homebrew’s logo deeply into my right shoulder. What did this moment represent, besides a strong conviction we’d never rebrand? It wasn’t a victory lap, that’s for sure, because it takes many years to prove you’re great as a VC. No, it was memorializing the decision to *start* Homebrew, independent of the eventual quality of outcome. Of course I believe that Satya and I have the potential and capacity to be excellent investors and now approaching our third fund there’s ample evidence that at least we’re not terrible and, hey, we might even be good at this. But that wasn’t what I was capturing when that needle jabbed into my skin, depositing a little black ink each time. What I was capturing — what I was owning and memorializing was that it was a really good decision.
There’s a tendency to wait for an outcome and then use that data to pronounce whether the decision itself was a good one or a bad one. Careers, investments, relationships — was it a success? Then it was a good decision, right? Oh it failed? Bad decision.
Not necessarily. Maybe it was the right decision, just a bad outcome. You should make that decision 100x more times, because the probability or magnitude of good outcomes are actually in your favor. In any system with relatively low cost of failure and repeatable game scenarios, it would seem that getting the decision right is actually what matters.
I meet people early in their professional lives who spend too much time calculating the anticipated outcome versus understanding why they were making the decision in the first place. This title versus that title. This salary. That equity grant. And so on and so on. Trying to reverse engineer the right decision using lists of pros and cons, versus an understanding of who they are and who they want to be. My advice to them is usually pretty simple — answer this single question and don’t let fear hold you back from making the right decision. If you build that muscle memory and apply it at each junction, your career will be fine. And you’ll end 2018 in an even better place than you’re starting.
[I use “place” symbolically, but you know, if you’re literally working at a place that you don’t like and think you want to make a better decision, many Homebrew companies are hiring]