Productivity Tip: Synchronizing tasks for the individual

This week's Productivity Tip... As a kid I used little Day Timer notebooks to keep track of my schedules and projects. Of course my duties in high school were minimal compared to today, but those pocket-able sprial-bound notepads were great for capturing and tracking all my "stuff." In film school I met a videographer who kept track of his schedule using a PalmPilot. I loved how, for years, my PalmPilot kept perfect sync with my Mac -- provided I put it in the cradle every day and hit the Sync button. Today, we don't have that sync button. The "cloud" has removed the need for it, right? Well, that depends.

Brain sync

There's a famous story of Charles Schwab, at the time the president of Bethlehem Steel, who advised Ivy Lee (his generation's Covey or Allen) that he could increase Lee's team's efficiency with one simple tip. That tip was to write down the six most important things you have to do the next day before going to bed. At the end of the next day, anything still on that list went onto the next day's six things, and so on.

Inspired by this, and by Federico Vittici's use of Drafts and Day One, I've started a similar ritual. Instead of one daily pass, however, I've started journaling in the morning (using Day One) and reviewing my tasks at night (using OmniFocus). You can do both of these using Drafts, in fact. Lists can be sent to Clear as tasks -- which I do if the day has only single-task items needed -- or OmniFocus, or Due, etc.

The reason I call this "brain sync" is that I now have, via Day One, a running list of my personal and professional thoughts and goals every day. Coupled with a focused task list, I can reflect on where I am at any point. Making the simple list at the end of the night helps me sleep better, knowing exactly what my priorities are for the next day. Waking up and jotting down thoughts often yields solutions to problems, but also keeps a running log of what my mushy brain thinks is important contrasted with the hard reality of my task list. The goal is to align them over time, as much as possible.

When to sync

The Cloud: Syncs all the time, in theory. If you use iCloud, your iOS or Mac device will sync more or less seamlessly in the background at intervals regularly enough to cause few issues for an individual user. With iCloud, the system monitors a specific folder outside of the app itself, so changes made on your iPhone to, say, a Byword document, will appear on your Mac when you open up the document there.

There are some issues with cloud sync, however. Depending on the mechanism, you might run into version conflicts. Services like Dropbox allow you to roll back, but iCloud really doesn't. Also, if you force quit an app while a sync is in progress and the app isn't using iCloud, you could end that sync session and wind up with problems. This is a rare one, but it's something to consider if you're the type of person who routinely "cleans up" their list of open apps on iOS.

Apps: If an app is using iCloud, sync "just happens." Dropbox also has a sort of background sync, and apps that are in the process of uploading data can continue to "stay live" when closed for up to 10 minutes. Provided you don't lose your network connection, that should be ample time for Evernote and other such apps to sync their data.

There are times when you will want to manually sync, however. In OmniFocus, for example, the default is to sync when opened. I also like to click the sync button if I've just gone through entering a bunch of data (after a review on my iPad, or if I've just powered through some errands).

Then there are some apps which allow you to see when a sync happens, or force a sync when you wish or maybe even require you to manually initiate a sync. Again, I recommend doing this before closing the app. When I move a timer to the next day using Due, for example, I like to pull to refresh the timer so my Mac isn't sitting there chiming for a couple of minutes before sync happens.

Paper: If you're using a mix of apps and paper, for best results sync at least once daily, then do a top-down check once a week to make sure everything is on track. It's sort of like reconciling your bank accounts.

How to sync

Cloud: I highly recommend using the sync service preferred by the application you use. iCloud is Apple's effort to push a ubiquitous sync solution in iOS. Unfortunately, as of this writing there are some serious problems with iCloud. Gus Mueller goes into the gory details, but I have hope that with WWDC looming, Apple is going to fix this.

OmniFocus uses Omni's own sync service, and I have almost never had issues with it. Omni's sync is now available to other apps from the company as well, which makes for a delightful experience.

Apps like Drafts and Simplenote use Simperium. There are tons of apps out there with Dropbox integration (I use Byword with Dropbox), and of course Google's products are all starting to get connected and sync up. Most of the time, all of this stuff "just works," and it works much better than it used to!

Paper: How you sync if you blend paper and digital will, of course, depend upon the mix of the two. If you're lucky enough to be able to easily transcribe your paper stuff into digital stuff, you're way ahead of the game. Things like the Livescribe pen are expensive, but you can also use Evernote to scan your handwriting and do its best to find your words (it does pretty well, in fact). Personally I'm not afraid to spend some time scribbling notes in my project books or notepads, then spend about 10 minutes a day transferring what I need to OmniFocus. Perhaps the best of all worlds is this fancy Evernote Moleskine, which I haven't tried yet.

What I do, now, is keep a collection of 3-ring binders. Each binder is a particular context, more or less. There's one notebook for home, comprising my DIY projects (repairs and improvements), tasks like checking on insurance and so on. There's another for work, which contains projects and plans for TUAW. Like Behance's Action Method, anything that needs to be done beyond a single-step is a project, and gets a sheet in the notebook. One sheet, that's all, for every single project I cook up. I wind up using leftover ruled paper I buy every school year for this.

I use dividers, emergent task planning sheets and the like in these notebooks, but ultimately those are all for my mush-brain to write out and try to analyze. Once I have a specific path organized and ready to go, I put in the relevant project tasks into OmniFocus or my calendar (or sometimes Clear).

This setup gives me the flexibility of being able to plan with sheets of paper -- and that's how my mind works best -- but digitize and distill the action steps needed to get there. Each week I sync up tasks completed and marked in my digital tools with the notebooks on the shelf, ensuring I can see progress towards the goals.

Each project has a page, with a goal. Each project has a set of tasks. Those tasks go digital, then are scratched off digitally, then on paper. If reshuffling and more planning are needed, I find it's easier to manage this in paper form, with notes in margins, arrows pointing to milestones, etc. There's a benefit to me to having all of this on paper and having to double-check things. This is actually a rather new system for me, so I'll be detailing progress and usage in posts to come. For now, I wanted to give a concrete example to anyone out there with so much as a simple notepad they use to track tasks. My recommendation is that you try to sync at least once a week, and consider tools to help transcribe your notes.


We're currently enjoying the best way to sync so far right now, but cloud services have their caveats. Network problems, data collisions and more can turn sync into stink. I find myself doing more work on paper first, then transmuting it into digital forms for dispersal and action. That way I have some form of backup for my thought processes. No matter what you do, consider a "brain sync" twice a day to help keep you focused on those most important tasks, whether you keep them digitally or on paper -- and never forget to back up your critical data!