"Undermining my electoral viability since 2001."

Do you like what you do?

Since getting engaged I spend more time thinking long-term about the world and my career. I've always had a yen for the big picture, but figuring out how yours truly factors in has taken on more urgency of late.

Some of it comes from explaining "what would you say ya do here" to a pool of putative in-laws who understandably have a number of questions. Part of it is needing to figuring out how I'm gonna cash the existential checks I've written with my existing career moves, to make good on my potential, to pursue the bigger-vision in more than a hand-waving context. A little bit of it is wanting to feel solid in an identity that's separate from the pop-culture caricature of Silicon Valley that's part of the current zeitgeist.

It's not a simple question. I have the most nebulous career and title in the world, "entrepreneur" and "founder". When I talk to people in the start-up game, I often extend the label to be "utility founder", like in baseball where you have a utility infielder; someone who can play shortstop, second base, or first or third in a stretch. The truth is I don't have a single job description. I have several. People in my field tend to get that. Filling multiple positions is par for the course in early-stage companies.

In the Aristotelian ideal a company has an org-chart with a bunch of roles, defined and routinized and efficiently run by competent professionals with years of experience. In startup reality you have a lot of people doing double (or triple, or more) duty operating to fill the boxes you want to eventually populate with dedicated staff. It's hard, but that's what founders sign up to do. And although it can be nebulous, this is actually the most awesome job description I could imagine. It's the only way I know how to operate, and transitioning from just "doing what I do" to understanding it as a discipline, and learning to get really good at it, is an exciting process.

It's not just my personal tastes — there are significant operational advantages to running this way. You have a level of agility that's impossible in more solidified structures. Gap-filling means that cross-functional coordination happens de-facto because the same individuals see things across multiple theaters of action. When it clicks, you can seriously outperform more rigid, stodgy organizations. That's one of the key reasons why well-run start-ups and small organizations can be "disruptive": demonstrating breakthrough productivity by re-imagining and solving previously "unsolvable" problems doesn't happen when you follow an existing playbook. That's how we roll.

At the same time not having a clearly defined role to play creates personal angst, especially as an organization grows. It can also create confusion. One of the key skills of being an entrepreneur is understanding how to build an organization, from a small inital cohort to an increasingly larger one, recognizing when and how to ceed control. Data helps, but there's no science to this; building a company that serves an emerging market or offers a new product or service isn't something that's templated. It probably never will be.

This is the only person I know how to be, or want to be: someone who dives deeply into a problem space and tries to build a solution. It started with things I could do personally, but quickly became about larger-scale goals. As I like to say, I met my current business and partners because I was trying to take over the government.

My personal history lends itself to technical insights and good turns of phrase. It's an unusual combination, but hardly an unhelpful one. To put it in geek terms, I'm persuasive human middleware. I know enough about how things work to be useful and insightful in crafting (and maybe even implementing) specific technical solutions, but I also have enough sense of the bigger picture and communication skills to coordinate and motivate across a wider spectrum, both within the project and externally.

What's been really exciting for me personally is figuring out how to work with other people who are truly excellent at some part of this process, and starting to create something where the whole becomes more than the sum of the individual smarts or effort. I still struggle with the urge to personally "superman" various things, to eschew the team process and go commando on a solution, but it's getting better. The "superman" mentality stems from having good results with isolated individual effort — people do what works — but the more I experience what's possible when a more coordinated process functions effectively, the more I want to have that happen.

Am I making this up as I go along? Yes. But that's a feature, not a bug. And making it up as you go along is different from pulling out of you-know-where. The experimental method still obtains: formulate hypotheses, test them, gather data, review, revise, iterate. To me this is the essence of any creative process, whether you're cooking dinner, making performance art, developing a product, or building a company. It's good to have a vision, but you never know where the journey will take you, or what you'll discover along the way. It's an adventure. That's what I love.

So, ultimately yes I'm pretty happy with what I do. Shocker. There are aspects that feel unsustainable from time to time — and it's ain't all rainbows and sunshine — but that's all part of the creative process. You have to rev the engine to push things forward, and not everything is going to be a win. You don't learn much without some negative results. As long as you don't burn yourself out or get stuck in overdrive, as long as you have balance at the meta level and stay healthy, it's all good. The badness happens when you lose the joy, or get in way over your head.

Real risks, but an appetite for risk is one of the entry requirements. Personally I wouldn't have it any other way.