Simplified, part 2.

I’ve been a huge fan of Squarespace for a long time, since I started using the service in May of 2009. Coming from a self-managed WordPress install, it was like a breath of fresh air, in which things were well-designed and easy to understand. You could add complexity piece by piece in sensible ways (if you wanted to) but mostly it was great for writing and posting quickly and attractively. The mobile apps were a nice encapsulation of the experience and allowed you to do the basic things you’d want to on the go.

I eagerly awaited the release of v6 this year after hearing so much about the beta as people used it and said how amazingly new it all was. How could the service possibly top itself? What wizardry awaited in this new release? The launch came, and I immediately migrated my entire site to the new service.

That was my first mistake. I soon realized that none of the categories I’d created over the past few years appeared in my composition windows when I was posting. Which meant that I needed to either re-create each manually, or I had a much bigger service issue that I couldn’t possibly fix. I contacted support and spoke to a variety of different, eager-to-help representatives, but the issue went unfixed for several weeks, during which I was afraid to add content to the site, not knowing how it might affect things. It finally did get resolved, though, so I can say thanks for that.

In that same span of time, I realized that the iOS apps upon which I relied for quick posts from my iPhone and iPad were slowly becoming hobbled. I could not edit posts I’d created in the new system on iOS because of the limitations of the way the apps handled them. I wasn’t doing anything nutty; I post entirely text, with the very occasional image (almost never). Over a few weeks, I wasn’t able to even post new entries to the site at all. Two days ago, I noticed that all the buttons in the iPad app compose window do exactly nothing now. Which left me with a post in the app that I couldn’t save as a draft or publish.

I stuck with a service that I’ve used for years, because I loved the flexibility. Which recently was whittled away to literally nothing. The iOS apps are now broken beyond belief. One would assume the company would be hard at work on restoring compatibility. But instead, it released a new branded note-taking app… because that’s what its users need more. I know notes are so hot right now, but it would really be better to have the entire service work as advertised. Even on the web, I’ve experienced slowdown, hangs, and complete failure as I try to do even the most basic things.

I finally tired of waiting for something to happen, so yesterday I migrated the site to a hosted WordPress install. I paid for ad removal and a custom URL. At least WP’s iOS apps do something (namely, work properly). The theme I chose is simple and pleasant, and I’m able to continue writing when I want to (infrequently) but when I post, it goes somewhere. I’m getting serious about dropping things from my life that don’t work for me or make things more difficult than they need to be. Sadly, one of my favorite web tools became one of those weights that needed to be dropped. I’m not beyond sweeping the leg when I need to.

No mercy, sensei.

Simplified.

I’m a tinkerer. I’ve always been a tinkerer, I’ll always be a tinkerer. I fiddle, I test, I try, I look up, I download, I delude myself into thinking it’s all in the goal of figuring out some better way to do things. In some cases, it happens that it’s true. More often than not, I realize that I’ve gone down a road I didn’t need to, but the journey of discovery usually pays for itself.

I love this stuff. I really do. But time is fleeting lately, between craziness at work and a new tiny person with some serious demands on my time waiting for me at home. I started to wonder: can I strip away small bits of complexity from my workflows and actually enjoy what most people would consider the “Apple experience”? I’ve long crafted elaborate workarounds to avoid using the default apps that ship with OS X and iOS, but they’ve matured to a point with 10.8 and iOS 6 that I’m entertaining the idea of giving them a shot again. The place that sees the most impact (unsurprisingly) is with productivity apps, traditionally my most fiddly bits. It took some intestinal foritude to take these first few steps, but in the interest of personal self-discovery, I suppose it’s worth it.

I’ve tried dozens of task/to do apps. I go through them like tissues in cold season. I landed on using OmniFocus for tasks a few months ago. I was initially impressed with how flexible it is as a product (I’m a big Omni Group fan), and how you can adapt it to how you wish to use it. What I came to realize is that I personally wasn’t using more than a few of its terrific options, which made it akin to killing a mosquito with a rocket launcher. So I’m giving Reminders another look. With the release of Mountain Lion, a dedicated app ships with the OS, and it’s on iOS already. So far, it seems to be doing an extremely servicable job for what I need, and Siri integration is really nice.

I’ve used plain text files stored in Dropbox for basic note-taking for a long time now. I’ve long preached the flexibility of plain text as well as the fun of plugging multiple apps into a single stored location and being able to try all kinds of things. As it turns out, about 60% of the notes I take are of no value to me after a certain period of time, and so I deleted a bunch of them. This freed me up from the mental burden of thinking I needed to keep everything around. Once I cleared that hurdle, I decided to try Notes again. As with Reminders, OS X ships with a dedicated Notes app now, and I wanted to see if I could get by with it. I’ll still compose anything more than a transitory note in plain text and keep it in Dropbox, but for basic capture, I’m sticking with this for now.

I just got brutally honest with myself and realized that I never actually do cool things like converting my plain text captures into Markdown and then emailing myself HTML snippets while automating task generation. I love the idea that so many apps allow you to do so much more than the basics, but if I’m being honest, then I can’t pretend I use all that stuff. So if the Apple apps are good enough, then why the question at all?

My main hangups center on how much I trust iCloud. I feel like maintaining folders of .txt files that I can easily point to and drag somewhere else *feels* right to me. I know I can dig out the Mobile Documents folder buried in ~Library, but it’s not the same. And I could back up my OF database in Dropbox and have days’ worth of copies to fall back on should the app fail for any reason. With iCloud, I basically have to put my trust in Apple that these bits of information, upon which I rely for my daily organization are going to be there when I need them. I’m not super comfortable doing this, but at the same time, I’m trying really hard to let go of my need to grip everything so tightly. Partly because I’m tired of the endless tinkering with my workflow, and partly because I’m envious of people who don’t even have these thoughts. It’s a sickness, you know. A beautiful, enriching, crippling sickness.

The experiment’s underway. All my short-term text is in Notes, and tasks in Reminders across my devices and Macs. It’s a strange feeling, using apps now that I’ve long derided as “not enough” and realizing that they are in fact, just fine. I don’t know if I’ll stick with this – it depends on my neuroses about this data and how long I can keep them at bay – but it feels oddly freeing. Like a weight has been lifted. Fewer moving parts, fewer options and switches, and a focus on something else.

Actually doing stuff.

(to be continued, I’m sure…)