It's easy to waste time worrying that you haven't done something you should have done when you don't have a clear picture of what you're currently committed to—both to others and to yourself.
The solution to that problem has three parts: A system, a habit, and a piece of permission you give yourself. I learned what I think is the best version of the first two of these from productivity guru David Allen's great book Getting Things Done and his writings and lectures on the topic since, but some of it boils down to good advice any of us might have gotten from a parent or grandparent. "Write it down" and "Measure twice, cut once" are just another way of talking about these same two ideas. As for the third, it is in essence the Discardian mantra: "Let it go".
The system part is to get this stuff out of your head (and your calendar and your inboxes, etc.) and keep it in one master place. That place might be a digital tool (like OmniFocus) or it might be as simple as a paper notebook. Whatever it is, make it easy to get your ideas and commitments into it as soon as they cross your mind.
Constant and fast capture has several benefits. Obviously, one is that you're more likely to remember your ideas and obligations if you write them down. Another is that the faster and simpler you make it to capture these things—by using OmniFocus's quick entry shortcut, for example, or by always having that master notebook with you—the harder it is for those thoughts to seriously distract you from another task at hand. You can park the thought in the right place and carry on with what you were already doing. The last big benefit is that the more you trust and use your system, the better you become at focusing on the right things at the right time.
As writer and teacher Clay Shirky said, "Behavior is motivation filtered through opportunity." In order to be making the right choice of what to do next, you need to understand your motivations (as I discussed in my last post) and make sure you have a complete and current picture of your obligations and options. When you know what you want to achieve and what you've said you'll do, it's much easier to identify the best match between the current opportunity—including your available resources and energy level—and the tasks on your list. But look out: If you don't have a purpose-driven list, other motivations will take over.
This is where the habit comes in. Until you pull back and consider those tasks (and the projects of which they are a part) in light of your goals and values, they can feel like a giant, depressing pile of undifferentiated to-do's.
How do you transform all that stuff you want to do (or someone else wants you to do) into something which will motivate you and keep you calm? You review it regularly. Every week you quickly look over the most important things. Periodically, you review the less important things. As you do that (along with looking at the past and coming couple weeks on your calendar), you'll add any commitments you haven't captured yet and you'll cross off those things which are complete or no longer necessary. By doing this every week, you will be able to trust on the days between that you will be soon returning to that big picture view where any date-bound obligations can be identified and scheduled. During this review—ideally through the very structure you use to organize things within your system, as I discussed last time—you will remind yourself of where these tasks and projects fit in relation to your higher level goals and the roles you want to be playing in the world.
It's easy to resist doing a review—it can take a couple hours for most busy people. But, as David Allen points out, "The additional amount of time and energy that you’ll have to spend, caught in the 'last minute' syndromes which will arise from avoiding a Weekly Review, so far outweigh what the Review requires, pure economics demand that you stop and do it – now!"
One of the things which keeps the review more manageable is to only be looking at the important stuff every single week; other things can be revisited on slower cycles. Use those shiny buckets I talked about last time—the roles you currently want to be playing in the world—as the identifier for what is important right now. For example, if you've currently got a bucket labeled "Awestruck Parent of a Beautiful Newborn Baby" now is unlikely to be the time that you also have in play that bucket labeled "Beginning But Getting Better Marathon Runner". It's fine to quickly note any less important ideas for the future—so you quit trying to carry them around in your head—but focus your time and energy on the projects and tasks for your active roles.
That brings me to the last element of solving the problem of worrying you haven't done everything you should and that is granting yourself permission to define "should". All of us can pile far more expectations on ourselves than any one person could achieve, let alone achieve while enjoying a happy, relaxing, rewarding life. Whether it's a single task, an entire project, a goal requiring multiple projects, or even something as big as a role you play in the world, you are in charge of deciding where it falls in your priorities. It might be currently active, it might be inactive and something you'll review and perhaps revive in the future, or you might exercise "completion by deletion" and drop it from your lists entirely. As I've said before, you can do anything, just not everything. Recognize that you will change over the years and filter your expectations of yourself to maximize your happiness and service to your highest values.
It is that permission to let go which is one of the essential ingredients to sticking with a system like this (and to getting back on track when you veer). Productivity guru and humorist Merlin Mann noted that "The danger of tracking everything is setting yourself up to a) have to keep revisiting them and maybe b) feel bad about not doing." This danger led to my labeling the inactive section of my system as "Things to think about again sometime". Thus I remind myself that these inactive things are not a commitment to do, just an acknowledgement of a thought that I will reconsider at some point in the future, so it can get off my mind now.
Getting stuff out of your head and safely parked somewhere in your system—whether paper or digital—combined with picking today's top few priorities is vastly more productive than perfect fiddly management of all possible tasks. The best systems will support all three aspects I've discussed. They will make it easy to capture an idea for later without losing focus on your current task. They will support weekly review for the important stuff and less frequent reviews for the lower priority things. They will enable marking projects inactive and getting them out of the way of your current focus.
Constant capture to a trusted system, weekly reviews, and choosing to let go of some expectations previously laid on yourself are powerful tools, but can be tough to get into constant use. The value of such organization and habit change can be profound, though. Coach Clarissa Rodriguez said, ''Even if you only save an extra ten minutes a day, over the course of a year that adds up to forty hours… Who couldn't use an extra week in their year?''