Since my life was turned upside-down in mid-2012, I haven’t had a good answer to the question “what do you do?”. I’ve been doing things, of course. I’ve traveled, consulted, advised, invested, and written. I spent a lot of time in museums and a lot of time staring at the ocean. I did things I wanted to do, and I did things I needed to do.
This has been the first time in over a decade that I haven’t had a full-time job for a long stretch. My knee-jerk response to that lack of definition was to jump back into a familiar structure. At the beginning of 2013, I rushed into a role at a startup that turned out not to be the right fit. Since then, I’ve cautiously evaluated the opportunities that have presented themselves.
To make things a little more surreal: a few weeks after I turned 30 this past October, Twitter went public, confirming that I never need to work again. (I’m still getting my head around that.)
So, what do you do when you don’t need a job?
I considered a bunch of options. Agonized, even. I thought about going back to school for subjects as diverse as computer science, philosophy, art, political science, economics, and architecture. I thought about writing full time. I was approached by VC firms, and by a number of startups looking for technical leadership. At my most frustrated, I even thought of pulling a jwz and flaming out of tech entirely, maybe to make music or volunteer all the time or who knows what.
None of that felt right.
When asked about my background, I usually mention that I grew up in DC and got my professional start there building software for campaigns and non-profits. This was well before the technology-driven victories of the Obama campaign, and even before Howard Dean’s pioneering use of online fundraising.
One of the instrumental figures in the Dean campaign’s use of technology was Clay Johnson, who I first met during Twitter’s breakout year at SXSW 2007. Clay immediately went on my mental list of people I’d like to work with someday. Since then, Clay has led efforts to open public data at the Sunlight Foundation, written an influential book on conscious information consumption, and has been fighting for procurement reform and innovation as a Presidential Innovation Fellow.
Several weeks ago, I found myself sitting on the couch, a little demoralized after exploring yet another job opportunity that didn’t feel right. My lovely and talented girlfriend put on an episode of The Daily Show in which Jon Stewart was (justifiably) ranting on a recurring topic: the inefficiency of the VA. At that moment, my train of thought: “Someone in tech needs to do something about this. I should do something about this. Who do I know who’s probably trying to do something about this? Clay.”
I’ve joined up with Clay, his talented technical co-founder Adam, and government relations whiz Sid at The Department of Better Technology. Simply put, we’re making software that makes government work better.
Now this feels right.
DOBT operates by a set of values that have, through experience, become very important to me: allowing and encouraging remote work, operating internally without titles, self-directed time management, and a non-dogmatic approach to building quality software products. I’ve seen enough business madness, and DOBT eschews it all. We’re working to build something sustainable at both a financial and human level.
Supporting diversity in tech initiatives has been a personal cause, so it was equally important to me that the people I work with understand the necessity of overturning the exclusionary monoculture that so defines our industry today. DOBT is not only a company with a commitment to diversity, but we’re advocating for a streamlining of minority- and woman-owned government contracting set-asides. Those reforms will unlock some five billion dollars for workers who have been economically disadvantaged.
Lastly, what attracted me to DOBT was the idea of working with a group of people who believe in government, and believe that technology can be a force for positive momentum in government. The HealthCare.gov debacle is just one example of what an uphill battle we have to fight, but it’s unquestionably worth the effort. For all its faults and frustrations, government is a pillar of civilization and deserves a foundation of well-crafted and open technology.
I still believe in technology, I still believe in government, and I still believe in startups. I’m happy to be putting that all together again with my new colleagues at DOBT. I hope you’ll consider joining us.
Addendum, May 5, 2018: yesterday, it came to my attention that my former DOBT colleague Clay has been publicly accused of sexual harassment and attempted sexual assault. I am extremely disappointed in Clay and saddened by this news. I was unaware of these allegations at the time we worked together — a failure on my part to do sufficient diligence. I hope to see Clay do right by his alleged victims in whatever capacity they deem appropriate.