All along, you’ve been laying important groundwork for making use of your tools. So in truth, you “got started” several chapters ago, since without that preparation you’d run into much bigger difficulties when it came time to start launching apps. But you usually only have to do that once—while this “get started” is something you may come back to when you Fail Successfully or Consider Everything.
The things you do when transitioning to a new system are similar to what you’ll be doing as ongoing processes after you’re using the new one. The differences, and they’re big ones:
When you start, you have a lot of things to move in, and this takes time. Once you are migrated, working in your new system should take less time than it does now. It will likely be faster than your old system too, but if not, you’ll get more bang for your buck out of it.
You might be learning new software. It takes time to turn all those menu commands and buttons into muscle memory.
On top of that, you’ll also be using your old system for a while longer, because your life can’t go on indefinite hold just because you’re getting organized.
No two ways around it: this takes more time than just sticking with your old system. But once you’re done and using your new system, you’re going to feel more on top of things than you do now, and when you work on something, you’ll know that’s the right thing to be doing then. Psychological studies show that people who are focused on their work in this way are happier. It may take longer for you to improve your productivity (as you define it), but this benefit should be a nearly immediate reward.
I’ve already made frequent mention of your “old” system: what you’re currently using that you want to improve upon. This probably caused great mirth among those readers whose “system” consists of an email inbox with 8,000 messages, hastily scribbled lists of things to do, and 30 pounds of paper they carry around in their shoulder bags.
Whatever it is, you already have a bunch of places where you jot down organizational ideas, store reference materials, and make notes about what you might want to do in five years. If you’re rather disorganized now, you might have many places where you do this. You should figure out what they all are, virtual or otherwise. Don’t forget the stack of papers and mail on your desk (or dining room table, if you eat in the kitchen), the voicemail and voice memos you might have recorded, any documents in the cloud that aren’t on your devices, or the widgets and receipts you’ve jammed in your glove compartment.
Finally, include your calendar. It’s not uncommon to stick with the same calendar you’re already using; that makes the next steps easier, but it’s not required.
Don’t do anything with those places yet. It’s enough to have a list of them. Spoiler alert: you’ll be working with this shortly.
You’ll be replacing a fair number of these places with your new system, but perhaps not all of them. The glove compartment is a nifty place to quickly stash things you can’t deal with until you get home. That’s why you’ll use pointers in your new system to check it periodically for anything there that needs attention.
You’re almost certainly using new software, and maybe a new gadget or two, as you’re getting started. Some folks take to these things as if they’re shiny new toys, while others enjoy the process about as much as blisters while they’re breaking in new shoes.
Your instructions are slightly different depending on which is you:
If you’re not a technophile, learn your new tools just enough to reduce friction when you start using them. It’s disruptive when you’re writing a document in a new word processor, to suddenly have to figure out how to use that footnote feature you’ve never touched before. The same thing applies here: know enough of the basics of your software and tools, such that using them isn’t a constant process of checking the online help.
But if these are shiny new toys, you might fall into the other trap: spending all your setup time fiddling with everything to make it “perfect.” You pick up your phone to set up an app, and 30 minutes later you’ve spent that entire time setting up the feature that downloads NASA photos daily for your wallpaper.
There are generic tricks for learning new software, which I recommend if you’re not happy about adopting new tools. New-toy people should try to limit their app setup to only these steps:
Click on every menu, and read the menu items carefully. Some of them will mention features you didn’t know exist, and the way menus are written can jog your understanding of when you would use it. (I discovered last week that TextEdit, the basic Mac text editor I’ve used for years, has fine-grained paragraph spacing; it’s not obvious but it’s buried in a submenu.)
Skim the table of contents in the app’s built-in help, on its support website, or even in the accompanying PDF manual (an endangered species, sadly). This gives you a sense of the terrain for the software, and will probably reveal features you’d never find by clicking around.
Read only the parts that relate to things you’ll do immediately, and skip what seems esoteric or less useful. But do make a quick note of what they are, in case you need them sooner than you think.
Open the app’s settings or preferences window, and note what options are there. As with the table of contents, you’re mainly acclimating to what the options are, whether or not you’ll ever use them. You might find yourself coming back here if something about the software is immediately annoying. If you see anything obvious that you know you want, go ahead and flip that switch. Don’t do this if you’re currently uncertain what it does.
A review period is the formal phrasing for “figure out every Sunday what I’m going to do this week.” It’s bookended by recurring tasks you complete with your task app: updating your projects, moving things around, sanity checking your due dates, and other maintenance. At the beginning of every review period, you decide which things you want to accomplish between then and the next review—I’ll explain how shortly.
The default timing for this is a week or two, since most of us have handy weekends when we can set aside some time to do this. Exceedingly busy people managing multiple projects may prefer to have shorter review periods to handle the extra complexity. The more often you review, the less time each one should take.
I don’t recommend less frequent reviews, at least not to start. Reviewing your system is an unfamiliar behavior, so get into the habit first by checking in frequently. Later on, you can lengthen your review periods if you prefer.
If you find that you’re not on top of your commitments as much as you like, your review period is too long. Reviewing your system is also how some of it gets sufficiently lodged in your head to have a sense of the big picture.
This one’s optional. A review period is too short to tackle any major project, only the parts of it that fit into it. On the other hand, New Year’s resolutions are usually troublesome because they’re too long: for half the year, you think you have plenty of time to get to it, and the second half, you realize you’re as busy as when you put it off.
A planning window is simply your scope for how far in advance you want to have things organized, with a rolling start date set to “now.” If it’s March and you have a three-month window, anything you intend to complete (or at least start) by June is in the scope of your system, and should get some planning and organizing. Anything beyond June is Somebody Else’s Problem, specifically, the problem of future-you who’s going to get to it later. A planning window is a deliberate decision to have a cutoff, for things too far in the future to worry about.
You already know what your first project is, but it may not have occurred to you that it is a project. You have a new planning system. The first thing to plan with it: using it. In my industry, we call this “eating your own dog food.” It’s a good practice.
Make a new project in your task app, and add a task to it: “Review the tasks and projects in my task app.” Set it to repeat with a due date at the end of every review period. This is a firm due date, as it’s not a fixed deadline, but the longer you go without, the more likely it is you’ll have productivity management problems.
What should you name the project? Depends on your personal style. You could create one project where you store all your “meta” tasks (that is, the tasks you perform in order to manage your tasks). I prefer to use one master list where nearly everything that recurs is stored: “take out the trash” is on the same list as “review my system,” but have different contexts, start dates, and repeat frequencies.
Switching from your old system to a new one all at once is an excellent way to drop important projects on the floor and miss your deadlines. If you do this, you’re relying on your new task app before you really know how it works, and you’ve shut down anything in your old system that kept you on track. Instead, you run them both simultaneously as you gradually migrate from the old to the new.
Add a recurring pointer for every place you identified in Document Your Old System. Your old organization and lists are no longer where you add new work, but instead are collection points for things to add to your new system. The pointer is a prompt to add things from each old place to your new one.
For places with lots of stuff, don’t try to do it all at once. That’s why you’re using recurring pointers to tackle this. When you work on moving your projects and tasks, do it until you have to do something scheduled, get bored, or get too brain-fried to usefully continue. This is also an excellent time to Use Sprints, so you don’t have to hit exhaustion before you stop.
However, one thing you do want to get to quickly is your calendar. If you’re changing to a new app, you’ll need to move your data over. (Look for an option in your old app along the lines of “export a calendar file” or “.ics file”; that’s the lingua franca of all calendar apps. Your new calendar app will have an import feature.) Either way, when your data is where it’s supposed to be, your task is to consider every future event and decide whether it’s hard, firm, or soft. Add at least three calendars for these categories—you can use more if you also want to say something like “Work Appointments” for hard events and “Family Chores” for firm events at home—and change upcoming events to one of the new ones. “Upcoming” is defined as “however far you need to plan ahead and know how much time will be available.” Don’t forget to share your new calendars with whomever else should see them.
As for everything else, it should be fairly straightforward once you’re used to your new task app. When you get to a project in your old system, add it to your task app, then flesh out its component subprojects and tasks. If your old system has documentation for the project you want to keep, the easiest way to do this is to print it as a PDF—most task apps allow you to attach that file to your project directly in the app. Otherwise, create a pointer to the document along the lines of “If you need to review completed tasks, go here.” (Also what you do if your old system is on paper which you don’t want to scan or take digital photos.)
Finally, cross out the project the project in the old system, and replace it with a pointer to your new one. You may still be using your old system as a starting point for a while longer; this pointer tells you to work with it in the new place. Continue using your old system for other projects until you have a chance to migrate them.
Once you have everything in a place well documented in your task app or elsewhere in your new system, keep the place if it’s an ongoing collection point that you’ll continue to use. Add pointers in your task app to make sure you go back to it regularly. Abandon places you will no longer use, and delete any pointers you might have created in your task app that send you there. Then do something with those places to make sure you no longer use them; for example, if you have a stack of to do lists that you used to regularly consult, file them away somewhere hidden so you’re not tempted to use them again.
Creating granular and specific tasks is also a habit you can start now:
Bad: “Once a week, work on moving my stuff into the new software.”
Good: “Spend 30 minutes taking pictures of the papers on my desk, storing those for reference in the cloud, and planning their followup in my software.”
Set it to due every so often, then deferred for a few days each time it’s done. Duplicate this task to set it up for your other places with a little editing, each with its own instruction for you. Make more important places recur more frequently, so you’ll get through them faster. (You’ll see this kind of task again, where you tackle a mountainous task with repeated but brief effort, when you Use Sprints.)
In addition to having regular tasks to move your old stuff into your new system, there’s one more reason to go to your old places: as quickly as possible, you want to look where anything urgent or due soon is hiding.
How you do this will depend on how you used to track these. It’s probably not necessary to scan anything more than a month or two old—unless, of course, somewhere in there is last year’s reminder to pay that annual bill that is consequential when missed.
If you know there’s a place that you won’t finish cleaning out for a long while, and something in there might bite you if you aren’t reminded of it, give it the fastest review you can for only those things. Don’t get distracted and make it a regular clean-up. You’ll get to that on the schedule you’ve already created.
If you can’t do this all in one sitting, it’s another recurring task. Set it to recur quickly enough that you’re minimally worried about where all these items might live. If you’re still concerned that won’t be soon enough, do all your urgency scans first before you move anything else. This is less efficient (since you’ll be reading every old list twice), but might induce greater peace of mind.
Here’s how you “naturally” migrate over time, in addition to anything you’re doing to move old stuff to new places. Anything new that lands on your plate gets organized in your task app (or someplace your task app points to), or stored in a collection point for later. No exceptions.
If a new item arrives with urgency attached, and you haven’t yet figured out how to make your new apps and gadgets fire off sufficient alarms, do so now. You can’t let “this is really important” be your excuse to backslide. Every habit you already have is trying to pull you back to what you used to do. You’re taking on this transition for a reason. Allow yourself to use the old habits for “important” things, and pretty soon you’ll be in the old system again, or in a state of permanent migration.
Painful. Don’t do this.
This is how you keep everything straight while you’re mid-transition. Set up a pointer in your old system to tell you to look at the new one, then set more in your new task app that point you back to the old one. At first, you’ll be using the old system’s pointers much more often, but over time your new task app becomes a more useful starting point. When you find there’s nothing worthwhile in the old system any longer, congratulations, you’ve migrated.
Now that everything’s in place, let’s go through how you’ll be using it.