The other night, I had a dream that someone asked me to come up with a bulletproof business model for news. I literally woke up in a cold sweat in the middle of night, existentially terrified that I couldn't come up with a way for news to be profitable on that kind of deadline. What were they thinking?
Then I went back to sleep and found myself in a hot tub full of developers, who tasked me with writing a 100-page book chapter that definitively solved identity on the Internet. Some nights, you can't win.
Those are two of the roles I play at work: someone who thinks a lot about business models and go-to-market strategies (although, thankfully, not for news) and someone who thinks a lot about technologies on the Internet and where they need to go. Another role is the guy who looks at the source code and figures out why it's not working; probably the role I play the least is the guy who writes the source code to begin with.
Ideally, all of these people would actually be separate, but one of the things about startups is that the founders end up playing the role of everyone who's missing, until you can find enough money to pay someone.
It's like you've got to be a hyper-generalist, which is lucky, because that's what I've always been: I'll happily write you some code, but I'll also put together some visuals in Photoshop, or create an audio story, or write a book. (Two, so far.) And it's fun. I'd actually hate to be pigeonholed into just being one thing. It's not something that's ever happened in the history of my career.
A long time ago, when the universe was younger, I was the Web Administrator at Oxford University's Saïd Business School. I was hired to manage the website, and I did that. But I also ended up writing a lot of code to power the website, which wasn't technically in my job description. And then, for some reason, I created one of the desktop wallpapers for the institutional computers. And word got around that I could do that, so I ended up creating images for events. And then people realized I was a useful person to have in conversations with visiting entrepreneurs, so I started being pulled into those. And that's how I met Ev and Biz, among other people, who were working on Odeo at the time. Biz became an advisor on Elgg, my first startup.
A lot of emphasis is put on founders saying "no" to things and having focus. But sometimes, if you just keep pulling on threads and following opportunities, you can find yourself in completely new places.
The personality trait that really works in your favor is optimism. I'm a hopeless optimist. Not so much about myself, necessarily, but certainly about the projects I'm working on. I tend to think that if I can only keep pushing in a certain direction, as long as I'm smart about it, keep evolving based on feedback and maximize the possibilities of meeting someone who might be able to throw the project in a whole new light, something amazing will happen. This is certainly a position of privilege (there is no such thing as a meritocracy), but the nice thing about the Internet is that "maximize the possibilities of meeting someone" doesn't have to mean being in the same room. Being social and loud can happen from afar, across many different kinds of media.
Having written this, I think this is also probably a problematic statement. Only people with certain lifestyles and resources can afford to do this. It's not, unfortunately, open to everyone. I do think that if you are able to have optimism, and to not just publish but discuss, in an open way, at length with people, you can create projects that move you forwards. I'm lucky as shit, and that's important to acknowledge - but getting the most out of that luck is still important.
More importantly, I think what I'm saying is that cynicism as a personality trait doesn't work. If you're constantly looking for the reasons why something isn't going to work, or why something out of the ordinary isn't going to be as good as the status quo, you're never going to get anything off the ground. The real answer is that, no matter how much research and planning you do, you don't know until you put something out there, and probably not until you've put something out there and continued to hammer on it at length. It's like a long, difficult experiment where the people who succeed are largely the ones who have managed to last the longest, by hook or by crook - and if that isn't optimism, I don't know what is.
I didn't mean to write about startups here; I have another website for those topics. I think I want to say something much broader: I believe in optimism, whatever you're doing. Not blind optimism - I also believe in research, feedback, personal evolution and, perhaps most importantly, not sticking with lost causes to your own detriment - but optimism, nonetheless. Let's call it informed optimism: it's stupid to not research what you're doing, get a realistic sense of your odds, and create contingency plans. Nonetheless, the people who always jump to the worst thing that can possibly happen are the people that rarely make anything substantive happen at all. You've got to be able to fill all the missing gaps yourself, in life as well as in work, and that only really works if you can know that tomorrow will be better.