Being alone, together

First, some inside baseball. This letter is just over 1900 words. It's actually two subjects in one, and though I considered splitting this into two issues, one topic segues neatly into the other in a satisfying way I decided not to give up. Also, I've chosen to embrace the fact that this very small list of subscribers all know they're signing up for my newsletter. (Some of you may be breathing a sigh of relief that this letter isn't even longer.)

I've decided not to promote this newsletter publicly (via Twitter, my website, or other Social Channels™), but I do want to share it with (a) people who would like it, and (b) my friends. In other words, I want to write to people, I want that list of people to grow, not shrink, and I want there to be a distinction between "my readers" and "everyone in the damned world".

For this moment, my plan is this: I'm going to email friends who I think might want to subscribe exactly once. I'll say to you four who are already subscribed that if you wanna forward this, especially to mutual friends who may like it, please feel free. If nothing comes of any of that, it's fine—a growing internet following is not why I'm doing this. This is why I'm doing this. But, like anyone, I do enjoy company.

How to be alone
On Tuesdays my wife and daughter go out for a weekly appointment, during which I go out to have lunch. It's the only time during the week when I can count on being alone.

In some respects, I haven't used the time very effectively—I usually piss away half 30 of my 120 or so free minutes riding to and from wherever I'm eating, and what's left doesn't allow me to do much more than sit quietly, eat, and make notes. But even that is a gift these days, and today it occurs to me: Tuesdays would be a great letter-writing day, and writing a letter over lunch sounds like a lovely use of my Tuesday time.

Though I almost never post to my blog anymore, I'm actually writing constantly. It's just been unusual for me to publish the things I write. In fact, in recent months (years?) it's been unusual for me to even write them down.

I have a bad habit of talking to myself as I walk, having conversations about things as if I were on a panel or a guest on an imaginary podcast. (Yes, it looks insane. I sometimes wear a Bluetooth earpiece or headphones to lessen the effect.)

On reflection, the things I talk about in these conversations are things I would write down if I were writing, and might then publish if I believed in them a little more. Often the things I talk about with myself are not that interesting. The imaginary podcast format is telling, because frequently my obsessions are tech- or tech-industry related. If this were an actual podcast, it'd be a decent if unoriginal knock-off of ATP or The Talk Show.

But, as asocial as it feels to talk like this out loud, these conversations with myself do seem to help me refine my opinions and understand what I think.

In the last week or so, I've noticed I talk out loud a little less. and write things down a little more. The notes I make aren't necessarily in a transmittable form. They have a tendency to meander. Some points are half made, others are belabored. But they're somewhere other than in my head, or the airspace immediately adjacent, which feels like an improvement.

For you process nerds: I capture everything in an iOS app called Drafts. It's a Markdown-savvy text editor with an inbox and a ton of "workflow" actions for sending the text you hit down into other services—Dropbox or Evernote, mostly—or to other apps via iOS 8's Share sheet. Drafts is meant to be a buffer, somewhere text is captured on its way to a more permanent home somewhere else. This letter is starting out in Drafts, from whence I exported it to Dropbox, from whence I opened it on my computer for copying and copyediting in the TinyLetter editor thing.

A lot of the notes I capture are functional: lunch orders, phone numbers, tasks, things that hang out for a short while before being filed or discarded. Others are more important, but as reminders or prompts for something I need to do or that I need to think about more. This use of Drafts is like a digital version of a pocket full of napkins, or a desk full of post-it notes. I have a setting turned on that displays the number of un-archived notes on a badge on the app icon. It has never yet been zero.

Finally, some notes represent thoughts, opinions, plans, ideas—the stuff I want to work through, if not share. These ones I've been exporting from Drafts into a journaling app called Day One, where I'll tag them with a major theme and the kind of writing I think I was going for (blog, talk, newsletter). To put all this another, much simpler way: I've realized that when I talk to myself I'm journaling, and that journaling need not be limited to capturing memories of events.

To date, nothing I've journaled has been pulled out and published, though I'm sure the practice has started to help sharpen my thinking for when I do write in public. A post for the Typekit blog is coming together in just one day instead of many days or weeks, and isn't as absurdly long as other things I've written. Plans and strategies for work are getting simpler and easier to explain. A journal can be a place where I can put down all my thoughts, then just pick back up the ones that seem most salient and helpful.

This isn't a fully realized system, let alone a silver bullet, but it's a thing that seems to help. It helps because it helps me remember the difference between writing and publishing, and that the weight of publication need not also be a barrier to writing, and that even writing or speaking to oneself helps you feel less alone.

It's possible I'll use this journal full of notes as a starting point for future letters. Or, I'll just sit down, eat a burger or a surprisingly delicate country-fried steak, and start writing from a blank page.

On Twitter,, and the new old web
My friend Mary posted the following to her Tumblr, and I read it after I started writing the last letter but before I finished this one: Decided that what twitter and tumblr amount to, or maybe what writing amounts to is the impulse to talk to myself. If we put it down for others to read, then it’s only to excuse the insane habit of talking to oneself, or because eventually one finds that the act of talking to oneself was really a conversation all along.
One of the things most on my mind since Brooklyn Beta has been whether Twitter as we know it is dying. A lot of very smart, very popular people seem to think that it is, between Twitter's unique outrage-magnifying quality—consider the endless stream of outrages like #ferguson and #gamergate, and how inescapable they seem if you even try to take in more than a tiny, private slice of Twitter—and the medium's unique ability to enable trolls, bullies and worse to harass people (especially women) on a massive scale.

This is one of the things I've journaled about, at first with the idea that I'd pull some bits out for my next newsletter or a blog post, now simply to make sense of it all.

The questions seem to be these:

I see people I like dropping offline or retreating to private accounts. I understand why, but it still makes me sad, like some friends or fellow regulars at my favorite bar have stopped coming by. I've toyed with doing the same thing, but it's possible I'm less invested, or that I'm protected by a white-male privilege bubble. At any rate, I don't feel urgency about leaving, but I do sense something changing, if not decaying.

I also sense a connection between discontent at what the social web has become, and this weird neo-retro movement embodied in projects like and newsletters like this one (or this one, or this one). Something about handcrafted HTML pages served by a dead-simple shared host, and writing delivered, human to human, over dumb old email, now feels warmer and more human now that we have a more baroque, more commercial interweb to compare it to.

It's a sense of warmth those of us who were around for Web 1.0 are *(apparently) trying to recapture. Though I don't have a account, I did just set up a tilde-style web server of my own, though unlike some others I know I'm keeping to myself.

Things like tilde accounts and TinyLetter seem like listening to records on vinyl. (Data point: other than live shows and streaming, vinyl is one of the few parts of the music business that's growing.) It's possible to appreciate the virtues of a simple web hosting account, or a plain, simple newsletter, only because we have the modern web to compare it to. In many cases, the new web is how we're promoting and finding audiences for the new-old web. Put another way: it's all the new web. Though parts of it are decorated in a retro style, it's all Cloud Computing under the hood, with the meta-story of its making carried via Twitter or Medium or whatever.

Even so, I'm glad there's some corner of it where I don't have to know what Angular is.

As for Twitter: I'm still thinking about it. Twitter, like the whole web, is actually made of people. Most of the people there are not evil, but some are. Most of the people there aren't hurting, but some are, and some of them are my friends. Most of the people aren't outraged; some aren't outraged enough. It's telling that the people who seem most despairing at the state of Twitter are also people who've dedicated years of their lives to making web stuff and participating in web communities. Twitter is our neighborhood, and it has broken windows we feel powerless to fix.

What I'm certain of is that retreating to private groups and neo-retro web page-making may be an answer, but it's not a solution. (Really, I think the kids coming up after us have taken care of some of the problems of social media for themselves—their social networks are private by default and leave no paper trail.)

I'm tempted to see all of this as an inflection point before what comes next: the time when we decide together what kind of web we want next, then go build that.

- DD