In 140: I’m moving back to Galiano Island and joining Etsy to form a new, distributed team to understand and improve the economics of Etsy shops.

After leaving Twitter at the end of last year, I knew I’d be taking a few months to think, talk, and prototype my way through what I wanted to do next. Those who know me will not be surprised that the longer I did this, the more my thoughts started creeping up the ladder of abstraction to the meta-issues: never mind what I want to work on, do I actually want to be working, anyway? What does it mean to have a job versus start a business, and what would push me towards one or the other? What are the conventions around doing a startup, why are they there, and are they important? How would my answers change if my situation were different? And so on. As a result, and with Tim O’Reilly’s advice to work on stuff that matters in mind, I started looking for opportunities to work on changing the nature of work. Three companies that I think are doing an exceptional job at that right now are Y Combinator, Kickstarter, and Etsy.

Why those three? I believe that all of them have the following property: there are people who will start businesses because these companies exist, who otherwise would not have done so. I think that’s a good thing for the world. I would rather see a commercial landscape made up of smaller groups of people acting more independently, with the vastly improved communication and coordination possible on the internet providing the efficiencies that society used to get from large companies. This is not a new idea; I first heard it articulated by my friend Christine Herron many years ago when she was a Director at Omidyar Network. Apparently she pitches better than I do: I never got her as an investor, but her description of eBay as a force for social good has sat in the back of my mind ever since.

I won’t go into detail on my thoughts on all of these companies, or others that I think are interesting for related reasons like Stripe, Shopify, and Uber. I do think it’s worth making the following comparison, though: Y Combinator, at one end of the scale, helps start relatively few businesses, but some of them will become huge and most have ambitions to do so. Etsy is at the other end: there are currently about 800,000 active shops, but most of them are tiny and always will be. The team I’ll be starting at Etsy doesn’t aim to change that, but it does aim to help make them more economically viable despite being tiny. I’m particularly interested in ways that Etsy sellers can act collectively to improve their economics: can they end up paying wholesale prices for supplies? Reduce their individual costs of shipping? Gain a better, joint understanding of how pricing affects the demand curves for their products? To borrow some terms from a classic essay on open source: how do we make the bazaar that is Etsy as efficient as cathedrals like Amazon and Walmart?

Of course, there’s a somewhat bitter irony in the fact that by working on this, I will not myself be starting a new business. Not this time around, anyway; one of my primary goals at Etsy (and they know this) is to learn from their successes, and I suppose from their failures, and become a stronger entrepreneur myself in the process, for the inevitable time when the startup bug hits me again.

There is still a way, however, in which the form of my job will follow its function: like Etsy sellers, who are empowered by the internet to run their businesses from anywhere, I’ll be working remotely, with only occasional trips to Etsy’s New York office. Not only that, but the default assumption for those on my team is that they, too, will be working from anywhere in the world.

This is a big deal. The freedom to live and work from anywhere has a huge impact on me and my family. San Francisco is an amazing place, as is New York, but these are not the only amazing places in the world. Should we decide to spend half the year in Canada, half the year in Hawaii, and then a year in France to start my kids on a second language, I want to be able to do that without feeling like I’m compromising my work or my career by doing so. My wife and I have the incredible luck to have the right to live and work in any of the US, Canada, and the EU; it would be a shame not to take advantage of that. That Etsy is letting me do this, not just as an individual contributor, but as a manager, and not just for myself, but for my entire team, is exceptional and, in my opinion, far-sighted.

Which is not to say that we’re planning to be truly nomadic. For many years, we’ve owned a house on beautiful Galiano Island in British Columbia - just north of the San Juans, for those who know that part of the world. Galiano is roughly the size and shape of Manhattan, but is, I like to joke, slightly less dense, with a full time population of about 1,100. It’s also just far enough away from Vancouver, the nearest city, to make a daily commute awkward. This makes for lots of privacy and natural beauty, but a limited economy. The community attracts artists and writers and craftsmen and, more recently, filmmakers and technologists: those who can do their work in relative solitude, but still plug into the larger economy around them. That’s never quite been us, in the past - because of the constraints of our jobs, we’ve always had to keep at least one foot on the mainland. It’ll be great to be there, and exclusively there, for longer stretches of time. It’s a fitting place from which to start this project.

I was pleased to find out while writing this that there’s a view of Galiano for sale on Etsy: the point of land in the painting below is the first thing you see to starboard as the ferry from Vancouver pulls into the dock. I’m looking forward to seeing it again on my way home.