Category archives: Work

In October I gave a talk at Monktoberfest in Portland, Maine, a small and intimate tech conference with a big impact in the industry. It’s quite unlike any other conference I’ve been to, which is explicitly the point. I’d been hearing about the conference from friends for years, and it somehow still managed to exceed all my lofty expectations.

Monktoberfest asks that your talk be something you wouldn’t be able to hear at any other conference. Mine was about values and how they show up at work and what happens when there is a gap between your stated and enacted values. It’s a theme that percolates through a lot of my writing and something I’ve spent many sleepless nights ruminating on, and giving this talk to such a receptive, empathetic, and compassionate audience was incredibly meaningful to me.

You can watch the talk here:

Seeing as I am personally allergic to watching any YouTube videos longer than five minutes unless I absolutely have to, I’ve also included a lightly edited version of the text of the talk below.

continue reading →

I’ve been thinking a lot about leadership lately, for no reason at all connected to the news or the state of social media or the way we’ve constructed an economic sytem that allows petulant man-children to set billions of dollars on metaphorical fire because strangers on the internet made fun of him while simultaneously pretending that homelessness is an intractable inevitability that can only be solved by brutalizing the unhoused rather than taking away those billions of dollars from aforementioned megalomaniacs.

Sorry, where was I.

continue reading →

The concept of “work” is a Rorschach test, an inkblot that you can project pretty much anything onto. There are definitions that speak of a meaningless Sisyphean grind inside an oppressive and cruel economic system designed to extract the maximum possible short-term value from all its constituent parts. There are also definitions that evoke the sincere joy of putting care and attention toward something worth nurturing, and shepherding its growth through consistent, deliberate effort. Your definition of work probably says more about you than the actual concept itself.

continue reading →

At any given point in my life I’ve wanted to be spending more time writing. This includes the tween years in which I wrote and published fanfiction every afternoon after school, undergrad when I studiously scheduled three blog posts a week despite having very little of substance to say, and that year and a half when I ran a daily newsletter that took over my life.

I’m very happy I chose not to pursue writing as a career. I’m very happy with the career that I do have, and I’m very glad that I get to keep writing for no reason other than to write. I have never pitched a publication not because I think my words are in any way precious (I desperately need an editor) but because I didn’t want to worry about anything other than the writing. I can afford not to think about the profit incentives of publishing or the imagined audience of an institution, and so I don’t.

Writing as just a hobby, though, means that I’ve never figured out how to carve out a satisfying amount of time for it. It was a thing I did for myself, which means I could always find a reason why it wasn’t as important as something else I needed to do for someone else. And because writing time was scarce, I didn’t want to spend any of it frivolously, working through anything other than Deep Ideas I’ve already been chewing on in my head for months.

I like that my thoughts come slowly. I think the writing I produce when I’m using it to figure out what I think is leagues better than the writing I do when I’m broadcasting conclusions. But it does mean that there are lots of subjects I want to explore that I discard because they’re not worth 3,000 words wrung out over 8 months, and while that’s not exactly a loss to the world I do think that prevents me from growing as a writer.

Essentially, inside me there are two wolves. One knows that the only way to get better at writing is to write more, and the other doesn’t ever want to publish anything I haven’t obsessively thought through for half a year. The second one has anxiety and should not be listened to, which is to say that I’m going to try and write more short things that may not be fully formed. Please do not yell at the anxious wolf.