One way I have described myself is as a “professional amateur”. I am both deeply proud and deeply ashamed of that. Let me explain.
For basically my whole career, I’ve been learning new fields and professions from the outside-in. While I have an undergrad degree in Urban Studies, which ostensibly prepared me for interdisciplinary work regarding cities (and you could argue that’s exactly how my career has turned out), in practice I’ve spent the past 15 years learning other stuff and basically pretending to be a professional at it. Design, programming, running a startup, tech policy, law, activism, “internet architecture”, market structure, venture finance. In every case I’ve ended up diving in despite not really knowing anything, and figured it out as I went along.
(An aside: it’s pretty hard to do this without the internet. Curious about history? Start reading some Wikipedia articles. Want to learn to code? Head over to Codecademy, then make best friends with StackOverflow. Confused by a legal term? Google it. Need to install shingles on your roof? There are YouTubes for that. So, it’s easier than ever to be kind of good at something. Which is so fun.)
I also enjoy lots of different things, and feel like I’m better than average at most of them, (though I’m sure that’s a fallacy): baseball, singing, carpentry, ice skating, writing, cooking, water skiing, juggling, tennis, playing drums, playing piano, rock climbing, etc. I am not the best at any of them, but I take a lot of pleasure from all of them.
The good way of looking at this is that I can confidently call myself a curious person. And generally think of myself as capable, Curious and capable. I like that. I can get behind that.
The bad way of looking at this is that it lacks focus. And probably dedication & determination. Feeling stuck on that music thing? Fuck it, go build a shed.
And, it’s in tension with the idea of a “Half, not half-assed” approach. Do less, but do it really well. Then move on to the next thing. I admire that approach, and really do believe it’s central to building a successful product. But it’s hard to pull off — as Eddie Wharton put it on Twitter yesterday: “the best ideas are easy to articulate, but hard to master.”
So, that’s the context. I’m not looking for any answers, but just putting that out there in an effort to understand my real self. But reflecting on this, perhaps there are a few rays of hope:
1) “Half, not half-assed” can apply to a lot of different things, and you could argue it’s more about tight execution and shipping than it is about a more broadly restricted agenda (37 signals, who coined that term, built lots of small, successful apps — though they ultimately shed them all and re-focused on Basecamp). Maybe it’s fine to have lots of interests, and to invest time in different things, but make sure you actually ship. And when you do, make sure it’s tight, focused, and not half-assed. (For example, USV has a relatively narrow investment thesis that constrains our outlook, but still ends up applying very broadly across sectors)
2) Perhaps having a “beginners mind” is a “deep” skill unto itself. It certainly fits with the VC business, where one hour you’re talking healthcare and the next, video distribution. As Andy points out, there are plenty of times when that’s not enough, but perhaps it’s something.
So, there you have it. For better and worse, here I am: a semi-pro, semi-proud, professional amateur.