"Undermining my electoral viability since 2001."

On the Challenge of Becoming Relevant

At the core of my ambition is a hunger to be relevant. This isn't anything special; you can sub out "relevant" for "important" and "important" for "powerful" and everybody wants to rule the world, but I've been thinking about what sort of longer-term career arc I'd like to have, and while I don't ever see myself beating the workahol or ceasing to be an entrepreneur I think it's important to have some notion of what I really want, and to see a way to get that while working at less of a breakneck pace than how I normally roll.

Sustainability is a key for the long haul. Sustainability and fulfillment. In the long run, I'd like to be able to move the world with my words, and have that be more than a hobby.

Specifically, I'd like to develop an independent platform as a pundit to promote and promulgate my own views and Just What Should Be Done in this here 21st Century. That's right, it's simple megalomania.

But seriously, I have had enough exposure to the world of politics to know that opinions matter, and enough experience working with up-and-comers to know that there are millions of hungry minds out there who are looking for something more than what they're currently getting from either the establishment of independent press. I want an audience that's big enough to matter. If at all possible, I'd like it if that were part of how I support myself and my putative family.

Figuring out how to get there from here is no small task. Traditionally if you wanted to be an opinionator of repute, you usually scrapped that together after a successful career in journalism, and/or because some publisher somewhere took a shine to you. In the internet age, the rules are quite a bit different. Here's what I see out there:

There are still amazing institutional perches. However, much as I might admire and follow the work of Paul Krugman I don't really think gunning for a spot on the NYT masthead is the best use of my time. I'm more interested in folks who have managed to hack out an existence in a bit more of an entrepreneurial model.

Occupying the grey area between institutionally-endorsed and bootstraped is Andrew Sullivan, who I agree with a lot less, but who shows that if you cultivate a large enough and loyal enough audience you can break six figures pretty easily. He had the benefit of years at The Atlantic, and the platform of Tina Brown's Daily Beast to launch his new venture, but still kudos to him.

Closer to my heart is Duncan Black (aka Atrios). He's had fellowships here and there, but runs his own show. It's his blog, and he posts pictures of his cats every friday, and late night links to prog rock videos. He also fundraises from his readers every year. I doubt he's making a killing, but he's kept it up for a decade, and again if you can get a couple thousand people to kick in, it's not terribly hard to start seeing a way to make ends meet. Another blogger of the same ilk (and another fave of mine) is Digby. She and Atrios show that it's possible to be a modestly influential voice absent institutional endorsement, and to make that your vocation.

Further up on the ambition scale would be Markos, who I still owe a debt of gratitude for helping me start down the path that led to where I live now. He parlayed a blog which he ran — and on which I was an early member — into what is one of the most powerful online political communities in the US. Critically, he owned his own platform, his own technology, rather than doing it on Blogger or someone elses's masthead. He gets to publish as he pleases, including doing a few books and a column for the uber-insidery The Hill along the way. He's still firmly rooted in grassroots organizing and activism — GOTV, fundraising, etc — which is less where I want to be, but the model of building a like-minded community around you and using that to enhance your relevance has a lot of appeal.

Less on the political side, I think what Nivi and Naval did with venturehacks is pretty amazing, and they've got the kind of meta/community road by starting up Angel List, though to their credit neither of them really uses that as a personal platform. I don't have a huge passion to comment on the mechanics of startups for the audience of start-up-ers, but I am deeply inspired by what they did in terms of changing the rules of the game and radically democratizing the process of getting funded.

Finally, as long as we're talking debts of gratitude, quick shout-out to Justin Hall, my original inspiration, who's been at it for 19 years and never made his blogging commercial. Still moved plenty of lives along the way, mostly by just keeping at it and sticking close to the edge. Like a well loved indy outfit, he's still true.

So yeah, how do you become a professional gadfly? Inquiring minds want to know.

Clearly at the moment I don't write well enough, on focused enough themes, or with the frequency that's required to build a real base of relevance. I've got a little bit of a thing going with my day job, thanks. But looking ahead a few years or more, I'd like to think about how to start establishing myself as a voice that people turn to and respect. At a minimum, it should earn me a few ego strokes.

This isn't easy though. Striving for relevance is an anathema to popularity — desperation, the worlds worst cologne. The question is how one goes about building a personal brand, a power-base, a mind share. Trying to do so with the topical issues and global politics is a lot harder than with the technical stuff I am proven at: there's a lot more competition, no way to objectively demonstrate expertise (talk is silver, code is gold), and you won't find people googling up your old blog posts to solve their problems. I frankly don't really know how to go about building a reputation as a thinker or writer outside my existing social sphere, and the idea of trying to do so directly is kind of... terrifying.

Maybe that's a good sign. It feels scary like getting up in front of an audience of strangers is scary. That's good fear in my book.

The practicalities of all this are still totally murky. Obviously I can't really do much for the next couple years, though maybe with some discipline I can make a start. Honestly I'm writing this half in hope that I'll get some good suggestions. Any tips from the peanut gallery?