On making things worth loving

It feels important to me to try to send this first letter to no one in particular*, before I've put out my link and asked people to subscribe. I have a long history of making (and talking up) big plans about internet things that I don't end up following through with. Now, when I give people the link to this newsletter, there will be no question of whether I'll write something or not. It's already been done.

(* Almost immediately after writing this I mentioned it to work friends, who immediately subscribed. So I'm no longer writing to no one or to myself—I'm writing to two specific people, plus maybe others later. That still feels better than blogging, which is writing to either everyone or no one. Thanks, fellas.)

One of the nice things about a newsletter is that keeping up with it feels achievable. I don't need to worry about what blog software I'm using, or whether I'm happy with the typography, or whether my link will get buzz or traction or if it will trend. In fact, I can write it from what has become my primary computing device in daily life, in the physical context that's become basically my whole life: baby in one hand, smartphone in the other.


This letter isn't about being a new dad (which isn't to say there won't be one later on), but I will say that having a baby requires you to either focus or perish, because there is simply no time or energy left to spend on things that aren't valuable. Every free, adult moment is precious. Conference trips like the one I'm on now, to Brooklyn Beta, are a mother lode of such moments. (I'm actually borrowing these newsletter-writing moments from the thing I'm actually trying to do—make a small change to the Typekit site—which is itself an interruption from what I'd love to be doing, which is working on my book. It's like the structured debt financial engineering craziness that caused the Great Recession, with debt obscuring debt obscuring debt, but for attention.

Brooklyn Beta's slogan/statement of purpose is "make something you love". The event—it's technically a conference, but there's a shaggy-dog aspect to the programming that seems obscured by calling it that—is itself made with love, and consequently people love it.

But I'm truly not sure that I have ever made something I love, and in fact the ability to make something with love can feel really remote, so it's hard to feel quite at home here.

I've been doing art-like things since I was 15, and for that whole time​ people have suggested to me that I'm intrinsically more left-brain than right. But that suggestion never quite seemed to crystallize into anything like advice about what to do with my life. Like: no one in a position to tell me what I should do in school ever told me I shouldn't be pursuing painting, or experimental filmmaking, or film criticism, but while I was doing those things I'd hear surprise (mostly from peers, not teachers or advisors) that I wasn't in a science program, or something more mainstream like business or law. (True story: I once horrified a sculpture teacher by using the word "cost-effective".) Instead it was like, well, I guess you know best what you're interested in—it just doesn't seem like you as I understand you.

Is it possible I'd have been happier in a comp-sci program, or trying to be an MBA or a lawyer, than pushing myself for a whole decade to learn about art? Am I a sciencey person putting on an art mask, or an artsy person with a bizarre need for logic and structure? More likely, having written it out, it's that both are correct, but being stuck between two types or models or sets of expectations is just a weird, awkward place to be, and not a very comfortable place from which to make work worth loving.

I don't mind where I've ended up—I can't think of too many paying jobs more perfect for me than product manager at Typekit—it's just hard feeling that the path I took should have left me with more interesting stories, interests or passions than I feel like I have. I don't think I'm lacking for stories, but a lot of the stories I do have about myself are covered by a layer of darker things. There are things I need to talk about to get them out of my head, where they fester and rot like dead fish, that would (completely legitimately) be classified as oversharing, but it's hard to think about other, lighter things, or to take in what's great about other people, over the stench.

As noir as all this sounds, this is what I see in the mirror Brooklyn Beta seems to holds up to me, where I'm comparing myself, my career, and how I feel about things to what I see in all the other awesomely talented people in this community. The tension I feel between a wish to create and a need for order is real, it's still here into my fourth decade, and it really feels like something I need to figure out as I think about what I want to put forth in the world.

It's a story totally about myself, a rather intimate one to boot, which makes it hard to tell under the best circumstances. It's probably an impossible story to tell in the context of startups and the web, and really, not a lot of fun at parties.

So what else?

I haven't decided yet whether I'm going to publicize this newsletter. Right now, it feels nice that I haven't put it Out There as something The Internet should find Interesting or Trendworthy, but I would rather it found its way to people who might want to read it. I'm open to ideas.

I think Kathy Sierra has taken down the magnificent, horrifying thing she wrote about being harassed, and the internet's culture of harassment. It's sticking with me as I think about the kind of world (and specifically the kind of tech world) I want my daughter to grow up into, but apart from that I feel I have nothing to add to the conversation except this: Andrew Auernheimer (let's not glorify him by using his handle like it's his name) is a terrible person. That his Wikipedia page identifies him as a "gray hat" hacker seems problematic given how much blacker his blacks are than his whites are white.

So far, I've seen a lot of iPhone 6es in real world use, and only one iPhone 6 Plus. The normal 6es were all being used by web designers, developers, and tech people, almost all of them male. The lone 6 Plus was being used by a lady in the waiting room at my daughter's pediatrician's office. This ridiculously unscientific poll makes me think in the coming year(s) we'll have a world where Apple has sold millions of ginormous phones, yet none of us will know anyone who uses one.

For my part, I've made my choice: iPhone 6, because the 6 Plus is just too much. Space gray, because in my heart I doubt I could ever be a white-iPhone person. 128 GB, because I'm taking a lot of video of the seconds after my baby was smiling and giggling. Unlocked, because I have a work-paid-for cell phone plan, but no chance of a work-paid-for device upgrade.

Looking forward to my world getting a few dozen pixels wider.

- DD