A Transformative Year

I have sometimes joked that I never know precisely what I will be doing from one year to the next. As a freelancer, I am dependent on both the goodwill of editors and the persistence of business models outside of my control. This means that my primary sets of income one year could have shifted somewhat the next and be entirely gone the year after that. It means I have to be fleet and agile.

In June 2012, I was a very busy lad indeed, as I often am. I was writing a lot: for TidBITS, Macworld, the Economist, Ars Technica, Boing Boing, and others. I had a constant stream of features and short work that was passing through my hands, and wrote a book later in the summer about Messages for Mac OS X.

In the middle of that, I decided to crowdfund a book on — well, crowdfunding. How to run a good campaign learning from lessons of those who had done well (or failed and learned from it).

My workload was feeling relentless and unending, despite it being both personally and professional rewarding. I wanted to own something from start to finish in the figurative sense owning the process and the literal sense of owning the results.  The crowdfunding book was a way to break out of that cycle and create something new.

It failed. 

(Technically, it hit about 10% of the goal of $35,000 in about 10 days, and I realized it wasn't going to make it, so I pulled the plug rather than watch it inch to failure.) 

I hadn't built an audience to which I could bring the book and from which I could seek funding. I didn't have a large-enough group of people who would advocate to their networks of friends and colleagues to back it as well. (I also mispriced the rewards too high on the lower tiers.)

I'm not much of a sulker, so I threw myself back into writing and programming and other work, got called by Jeopardy! and won two episodes (taped in August, aired in October), and went to the XOXO Festival/Conference in Portland in September. In October, I took a trip north to speak at Çingleton Deux in Montréal. 

Those three events were a one-two-three punch for my professional life.

Winning Jeopardy! meant I knew I'd have a cushion of cash that would let me pay the family bills while potentially changing my mix of work. (The show pays out a few months after taping.)

XOXO blew the top of my mind off, and helped me realize that if I wanted to write that crowdfunding book, I needed to learn more, share what I learned, and build an audience that would be eager for such a book. It also thrilled me to hang with hundreds of like-minded people interested in changing the equation around creation, production, and distribution of arts, crafts, and more. 

Çingleton was a terrific and fun event for the camaraderie (so many of my favorite people from the tech world — many of them dear friends — were there), but it's also where I met Marco Arment face to face for the first time.

I came back to Seattle, and pitched Marco on me becoming editor of his just-launched venture The Magazine. I pitched the folks at Mule Radio about launching The New Disruptors. He said yes. They said yes.

I became editor of Marco's publication, and started devoting 40%, then 50%, eventually more than 75% of my time to editing it. We developed a great working relationship that let him focus on Instapaper and the art direction of our periodical.  

The podcast launched in late November and fairly quickly developed a modest but loyal audience. It is the thing I have done in my life that has generated the most feedback and the most positive response. The show is apparently changing people's lives by giving them the inspiration from the guests on the show to move forward in their artistic and commercial pursuits. I'm learning so much, and regularly get to talk with creative people who give me the same sense talking to them as I had at XOXO.

In April, Marco sold a majority interest in Instapaper. He and I talked then about the future of The Magazine, and it was clear that he had solved the challenges he had put in front of himself, and was looking for something new. I made it easy by offering to buy the publication; he made it easy by structuring a deal that would make it work for both of us. We closed that deal June 1.

The podcast just passed installment 27 this week — more than six months of weekly episodes. The Magazine  just came out with issue 18, about two-thirds of a year's worth of every-other-week issues, and the one-year anniversary is fast approaching.

I still write and contribute to other publications, and miss some of the variety I had. But I spent about 85% of my time in June 2013 differently than I did in June 2012.

That book I planned to write — I haven't forgotten it. But I know the title now. It's called The New Disruptors , and it will capture knowledge across my experience in making The Magazine work and from the guests on the podcast. It's coming, but not this year. That's for 2014.