Endless shelves

Dropbox is raising their prices, as is seemingly every other digital service of late. So I’ve been scaling back where I can. Dropped Netflix and Hulu down a level, canceled a few subscriptions here and there. There’s an intentional inertia to these services (eels, John calls them) that makes them hard to shake. If I get rid of Dropbox I have to rejigger how 1Password works, for starters, and I can’t even remember what all other services I have syncing through it. What will break if I stop using this? Do I even feel like figuring that out? It’s exactly the kind of annoying project I hate taking on, but if I don’t take it on, the procrastination gets rubbed in my face every month to the tune of $11.99 + tax.

And that’s just the practical inertia. There’s also the sort of emotional intertia that explains why I still have unopened boxes in my closet that have been with me in three different homes now. The mental energy one needs to go through old shit, to actually look at it and process it, is not an energy I tend to have in abundance. That infinite closet of cloud storage means we can pile all kinds of shit in there. You don’t even have to stack it if you don’t want to! The shelves go on and on and on. A rummage sale of remnants of your own digital life.

But I am trying to shake it, trying to have less, even digitally. It got dark fast earlier today (the today of when I wrote this); a storm rolling in. I found I was able to redirect energy I’d thought to use on a run to finally start cleaning up Dropbox, the biggest of my infinite closets. Abandoned projects, abandoned blog posts, photos of when I was fat, or sad, or fat and sad, or with people I don’t get along with anymore, or that I regret losing touch with. And good things, too, of course; things I’m proud to have written and made and had completely forgotten about … and hey, all of my hoarded pug photos are now in one place. More of a timesaver than you’d imagine.

It’s weirdly emotional work, just tapping away at my arrow keys, hitting command+delete on every third item or so. But it’s healing in a way. Digital or analog, it feels nice to unburden, to put things in the trash. It wasn’t taking up space, but it had weight. Feeling lighter already.

Fits and starts

My habits go in fits and starts. Discipline is hard for me. But I stick with more than I don’t, eventually, and I’ve learned to be easier on myself when things slip. I used to get frustrated about my bullet journaling habit, for instance. For a week, two, three, I’d use the shit out of that thing, and then suddenly, for no particular reason, a week would go by where I didn’t even carry it with me. And then I’d have a mini-existential crisis about it. No good.

Like anything I intend to do regularly — exercising, writing in my journal, day planning, practicing piano, eating vegetables, whatever — I think I’d be a happier, healthier, and more productive person if I did them every single day. And I probably would. But I know I’m a happier person if I don’t beat myself up about not living up to that standard.

Moving forward by degrees is still moving forward.

Seeking momentum

A friend who’s working on a new book (hi Corey!) asked if he could pick my brain about book marketing, seeing as I’d recently released one. Most of the advice I was able to share was just stuff I’d learned from others. Abby Covert sent me a very nice and helpful email of tips when I asked. My friend Brian, a great designer, let me pick his brain a while back about how to communicate better with designers and the AIGA crowd. And ABA connected me with Leslie Zaikis, who sent all kinds of lovely checklists and ideas to help launch and promote the book. There were more. And I suspect someone will be picking Corey’s brain a year from now with similar questions for him.

I hope I was helpful. But the truth, as I shared with Corey, is that I feel like I limped over the finish line on Writing for Designers. It was tough because writing is hard, and because it was my first book, and especially because the process of writing the book overlapped with some really difficult stuff in my personal life. I didn’t have much energy to do nearly as many of the promotional things I would have liked to do before, during, and after the launch back in October. Which isn’t to say I didn’t do anything; I organized a launch party, I sent SO MANY emails, I did a webinar for one meetup group and visited another in person, and lots of other little things here and there. But I felt like I’d left a lot still sitting on the table.

So I’m trying to get back to it. A few opportunities have sailed, sure, but October wasn’t that long ago. The book isn’t even six months old. And it just came out in print a little while ago. I’m in a steadier place now, and I’m trying to use this place to build momentum. I know from experience that you can’t force it. A little bit each day, then a little bit more.

So I’ve been trying to write and tweet more, about writing and design, but also just in general. I’m trying to be zen about having done the best I could at the time, even if it was less good than I wanted, and continuing to do the best I can going forward. I think that’s the real best advice I have to offer: do what you can today.

Shut up, you

Been using the app Streaks for close to a year. I know this because I borrowed the idea for a “Don’t Die” habit from @hotdogsladies, and that one is closing in on 365.

Habit tracking is about building habits, right? Obviously. You want to read more, so you make “Read for 5 Minutes” a habit, and if you get used to doing that, reading for five minutes or more a day becomes habitual, to where you eventually don’t need the reminder. Except that’s not really why I use it. It’s not the main benefit for me, anyway.

The main reason I track little “good things to do every day” habits is so I can tell the ugly little voice in my head SHUT UP, YOU. If I’m putting too much pressure on myself, or was just unable to pull off any uniquely productive work in a day for whatever reason — I didn’t write anything worthwhile, didn’t take any good pictures, maybe didn’t even leave the house — I can still look at Streaks and say “Today wasn’t so bad. You read. You texted with a friend. You did DuoLingo. You flossed. You ate a vegetable.” And so on. Or, if I didn’t do any of those things, I can still say “No big, man. We’ll get a jump on it tomorrow.”

I mean, I’d rather not be someone who has to regularly remind himself that he’s not a worthless piece of shit. But I am that someone, so I do. Have to remind myself, that is. And habit tracking helps.

Write every day, yes, fine, I’m trying

My journal is full of entries, my Ulysses inbox is full of notions and half-starts. So I’m writing a lot. I’m writing a lot. Good. Great. But I’m not quite getting to what I want to with a lot of it. I want to be on that Austin Kleon wavelength, you know? That easy, collected, curious tone of a blog written by someone who knows what they’re into and what they’re about, and also knows what people are into about them.

This is maybe the fifth post I’ve started writing tonight. Gotta finish something to be able to publish something, so I’m gonna commit to publishing this one now and keep going.

The difficulty isn’t word making so much thing making. I can make the words go all damn day. The first draft of my book was twice as long as they wanted (whoops). So that’s not hard. Laborious maybe, but not hard. It’s the discipline, the shaping, guiding the words somewhere, toward a thing, a unit you can post and share and promote … or at least pick a damned title for. That’s hard. For me, anyway.

My buddy Rob tweeted recently about not trying to make his posts perfect, and instead just publishing more, which I think is a great sentiment. Perfectionism is a big bad in my productivity rogues’ gallery. But I don’t think that’s quite what I’m wrestling with lately.

“So what am I wrestling with?”, he asked himself, in the hopes of prompting an answer from within.

Yeah, not sure.

I think some of it, tonight especially, has been tripping over … what, ambition? Lack of discipline? Something that starts small and might make for a nice little post blooms out into stubs for several posts, or an idea for a project, or no wait maybe I’ll start a Twitter thread about this! So instead of one simple little finished thing I have five little unfinished things or one big unfinished thing, and in either case they’ve sort of sucked the air out of the room.

My experience with these things is that it’s often a matter of habit. Get used to stopping, proofing it, naming it, hitting publish. Sometimes to finish you’ve just got to stop. So let’s.

(Update: Wrote this several nights ago and not sure why I didn’t publish it? This is maybe a different problem.)

Digital junk drawers

There’s a joke that having a writing deadline is the best way to get your house clean. Personally, I channeled this form of productive procrastination into digital spaces while getting to a finished first draft of the book. This was also partly out of thoroughness and desperation — “I know I’ve thought thoughts about this before, did I write it down? WHY DIDN’T I WRITE IT DOWN?”

During this procrastinatory polishing, I cleaned out and killed:

  • An old Scrivener project for the book that I started before the contract was official
  • An old GitHub repository for the book I never really made use of
  • Various text drafts in orphaned folders from when I imagined tackling a similar topic as a self-released iBook in 2014
  • My entire personal Evernote archive
  • nvAlt and thousands of associated text files
  • A work-specific journal in Day One with a few hundred entries
  • Several misc. folders of app screenshots
  • Dozens of mindmaps that had built up in iCloud that I thought for sure I’d need again but were all junk
  • Thousands of junk bookmarks in Pinboard from some social media automation I set up back in the day
  • Two underused IFTTT accounts
  • Six or so novelty Twitter accounts I’d never updated after the first month
  • And lots of other things I’ve already forgotten about

I also processed through a dozen or so analog notepads and small paper notebooks.

Most of this stuff was garbage. Just noise. With ever-bigger hard drives and near infinite cloud storage, our digital closets can be as big as we want them to be. But I’ve found that that’s not without a psychic cost. I felt like I was trying to do my work inside of a giant junk drawer. The elegant chamfered aluminum edges of a closed MacBook Pro can bely just how untidy things really are within.

Cleaning out my digital workshop out in this way helped me feel more productive with the tools that I did still have, and allowed me to approach my use of them with a clearer purpose. I actually use Pinboard now, for instance, and it’s become part of my blogging workflow and book marketing workflow. Bear — which I used to replace nvAlt, Evernote, Apple Notes, and an analog notebook of lists — has fewer notes than any one of those collections had previously, and is actually useful to look at now.

Feeling like I had permission to do this was one of the biggest side benefits of writing a book. Having a very specific project, with a signed contract and a due date, eliminated other possibilities (in a good way), which eliminated excuses to hoard digital things, and gave me more actionable clarity on what was still valuable. “Is this going to help me write this book? How about the next one? No? Then it’s gone.”

(Don’t worry — my PUGS PUGS PUGS folder is still growing exponentially.)

Sketching a blog post

Used a couple of Sharpie twin tips and my Baron Fig Mastermind pad to prototype my latest post for the Brain Traffic blog. Normally when I use pen and paper in my writing workflow it’s very messy and haphazard — notes jotted in random places, maybe a partial mind map, maybe a bullet point of outlines. This time I pushed myself to be very deliberate. It only took a few minutes longer than my usual approach but ended up being much more useful.

It was fairly easy to translate it back into an outline, though I ended up restructuring things a bit. The funny thing is I think this sheet does a better job of explaining the main ideas than the post does. Sometimes sentences are overkill. 🤷🏻‍♂️