Summer explorations, part two: The serpentine path of satisfaction.

Part one of this series is here.


As I said in the last post, splitting task data was something I’d not done before, and it became a very interesting scenario. I toyed with the idea back in July, but it was purely a theoretical thing, a thought technology and not much more. It didn’t stick then. In fact, it took seismic shifts in my daily routine and workload to precipitate the change and have it remain intact. But that happened in the past few weeks, and now I’m using two separate apps for work and personal tasks as opposed to filtering those things in a single app.

Once that decision was made, the next thing that happened was a realization that the way I think about “work” and “home” are drastically different–but I was managing them the same way, with the same overhead, filtering, tagging, etc. It didn’t make sense anymore. When everything is in one app, you start playing with filters and views to separate things you don’t need to see in reasonable ways. Eventually you hit on something that works, and you’re happy. But what I realized as I broke this data apart was that the things I want and need to accomplish in my personal life are vastly different from the things I need to accomplish at work. More importantly, the way I think about these things and the way I set about trying to do them really ought to be different too.

So I stepped back, with two disparate data sets, and thought about it. Todoist is a perfect tool for work, with team collaboration, web integrations, and cross-platform support. But what’s the perfect tool for everything else?

I’d been using 2Do for the past few months, and I’m a big fan of the app. It totally changed the way I think about information, how I organize it, and how I access it. I was late to that party and I’m far from the only fan, so if you’re interested, I encourage you to read these other great posts.

But 2Do started to feel (as flexible as it is) like more than I needed for this. So I did what any rational person would do in this position. I tried 47 other apps.

I began with redefining the things that happen in my personal life: there are “reminders”, which are things I need to remember, usually at a certain time. And there are “tasks” which can be things that need to get done but have no date—or things I’d like to get done, whether tactical or aspirational. I took anything without a date and created individual lists in Notes. I told myself I’d refer to them on a regular basis.

Mm hmm.

I went back to Reminders, like a gentleman. Built-in, deeply integrated, and simple as can be. Set up a few lists. The perfect place to store the things I need to be reminded about. Even does those cool deep-link things between apps as of iOS 9. The Notes idea, however, quickly became a weak spot, so I pulled those items into a single note in Drafts, which I am in all day, every day. Figured if it’s right in my face, I can see it and take action. I would look through that list each day and if I saw something I needed to do that day, I would highlight it and send it right to Reminders for attention-grabbing. It was flawless! Until it wasn’t.

Reminders is great because of what it does, which is exist on all your devices without a bunch of extra effort and mostly capture things in a reasonably expedient manner. But what it doesn’t do is allow you to make changes to those items easily and quickly. Or sometimes sync reliably (I had weird duplication of tasks, and stuff marked as done come back from the dead multiple times). All it takes is a few cracks in the facade, and I’m running. So while in principle, having all those unchanging things (bills, medication alerts, household stuff) always available on any new device via iCloud, it just didn’t feel like enough to take the throne.

More disappointingly, even though I adore Drafts more than life itself, it really isn’t the place for me to house my tasks and take action on them. The idea of a single Markdown list of the things I want to do was intoxicating, but it didn’t fit with my mental model of how I manage things I actually need to do.

Then I went back to Wunderlist, which I’ve used in the past. Wunderlist is cool because like Todoist, it’s web-based, so you can do some cool stuff with it. The app’s come a long way and features excellent things like natural language capture now. But between some syncing weirdness, some UI glitching on the iPad, and general malaise, I decided within a few days that it wasn’t going to be the winner either.

Then I snapped entirely and put everything back in 2Do. I wiped all my previous data one Sunday morning and decided it was the right place. I told myself I would change the way I think about organizing things (more capture, more action, less fiddling, less overhead) and I was convinced I was done.

Until about 45 minutes later, when I re-downloaded OmniFocus, installed it, and put everything in there too. OmniFocus, my longtime on-again, off-again girlfriend, with whom I share history, with whom I am not truly complete, despite my weary wanderings.

For the next 36 hours or so, I had all of my personal life in those two apps. And then I just freaked out. No, seriously, I did. I had a baby anxiety attack, quickly righted the ship, realized I’m a total asshole, thanked the heavens that this was my biggest problem right now, and just said fuck it, it’s going to be OmniFocus again, and that’s that.

The more I thought about it, the more I realized that the way OmniFocus organizes and displays information is what I was looking for right now. It does bulletproof reminders and due times. And with what I learned about not using due times and surfacing things at the right time when I need to see them, I figured out what I needed to do.

If you’ve made it this far, I truly am sorry. And thankful. We should hang out.

So.

Anything that either has to happen at a certain time or should happen by a certain time gets a due date in OmniFocus. Everything else sits across a handful of projects. Flat hierarchy (for now), no folders, no sub-projects, none of that. Simple. Barely any contexts. Contexts are a luxury now. I only create one when absolutely necessary. I have four perspectives: “Today” (due and flagged), “Available” (everything without a due date), “Wait Up” (stuff I’m owed or stuff I owe – good for work and personal life), and “All” which is just everything, in case I ever need to dive in. I can use Drafts and Siri for capture everywhere, and things like MailDrop and calendar integration as well.

The idea is: things I need to do each day (due) show up no matter what. In addition to that, I comb through “Available” each morning and choose one or two things I really want to get done–and think I can during the course of that day–and flag them so they show up. I have to be brutally honest with myself, and only pick those one/two, but it’s made me start to plan around how I want things to get done a bit more, instead of just making lists and never actually doing them. Last week alone, I cleared about four or five little things that had been hanging around just because I pushed myself.

And therein lies the big lesson.

This isn’t about apps, or systems, or UIs, or web integrations. It’s about getting serious and allowing myself both the flexibility to do things, and not do things as life dictates. It’s about changing the way I think about work projects and the way I think about my personal goals, so that both get accomplished in the best way possible. By changing the way I visualize and organize, I’ve been able to reset what my actual goals are, and start clearing items out. But it wasn’t the apps. It required a serious mental shift, and I had to be ready to do it. I wasn’t before. Things changed, and conditions became favorable, I acted on it, and I’m pleased with the results. I still have lots of work to do to move through some longtime lists I’ve been carrying around, but the new ideals I’ve created will lay the foundation for how I manage those things going forward.

Final chapter: after all this nonsense, what does it all mean? I realize some things about myself (again) and crystallize how I want to think about things for the future.

Author: Seth Clifford

I'm here for the open bar.