There I was, simultaneously overwhelmed and paralyzed by something that should have been a gift: a completely free day with no demands on my time. I’ve been on sabbatical for the last few months, yet I haven’t felt this overwhelmed in years.

The problem

At the root of my overwhelm is the fear of not making the best use of my time. I’ve been working since I was 15, and my biggest problem has always been the lack of free time. Now, faced with a wide open calendar, choosing what to work on leads to analysis paralysis.

Is this really the most impactful project to spend my morning on? What about my running deposit, that always takes at least an hour, shouldn’t I start there? Isn’t that project dependent on finishing this other project?

As of this writing, my task manager has 549 tasks spread over 52 projects, and questions like these cause me to obsess over task choice instead of actually performing work.

I’m a long time follower of David Allen’s Getting Things Done productivity philosophy, but until very recently, choosing what to work on has been relatively easy, since the prioritization of my tasks was driven by deadlines given to me by school or work.

This sabbatical has made it clear that my task management system was highly optimized for reacting to demands. I’m now seeing that my system is ill equipped for proactively managing how best to allocate my time.

What I need is to simply show up, know what needs to be done next, and get to work, while at the same time having the confidence of knowing that nothing will be overlooked.

The solution

After kicking around a few different ideas, I’ve landed on an approach that’s helping me keep anxiety low and execution high. I call it bird’s eye planning. Think of a falcon surveying an expansive swath of land, narrowing into a single section, zooming in to find a mouse, then diving in for the kill.

The stress and overwhelm I was feeling before stemmed from trying to assess every potential project and deciding which actions to take from there. It would be like the falcon’s gaze darting across the entire swath of land, trying to identify all mice, then choosing which to dive in on.

Now, I group all of my projects into categories and time box my calendar according to those categories. When I’m entering a time box for a particular category, I spend a few minutes surveying just those category’s projects, a small slice of all my open projects, and only then select the tasks I intend to accomplish in that designated window of time.

By scheduling time boxes for each category throughout the week or month, I can rest easy knowing that I don't have to make progress on every possible project for a category while I’m in that category’s time box. Projects that don’t get worked on today can be picked up in that category’s future time boxes.

Even when a category is brimming with projects, I try to only keep one or two active at any given time to keep the decision making scope as narrow as possible. As active projects get completed, on-hold projects get activated, and new projects get added to the holding tank, patiently waiting their turn.

Identities as categories

While the categories can be anything, I’ve found a lot of benefit to aligning them with my desired identities. In my post Forget the balance, focus on deposits, I describe how I think of these identities as “life accounts” in which I make regular "deposits" of effort and attention which compound over time.

10 of my projects support my desire to grow into an insightful writer. The identity of "Insightful Writer" is one of my life accounts, and therefore has a regular set of timeboxes into which I make consistent deposits of time and effort. This regularity allows me to confidently spend today’s Insightful Writer time box working on this very essay, knowing that I’ll be able to chip away at my other writing projects, like enabling comments on this blog, during a later time box.

Conclusion

While I discovered this planning tactic from a place of time abundance, I think it can also be applied when you’ve only got nooks and crannies of free time to work with. In fact, it’s at the heart of the “wheatgrass shot” analogy in my last post on Blocking burnout by holding space.

If you’ve got a lot of projects competing for your attention, give bird’s eye planning a try. Group all your open projects into categories, time box your calendar according to those categories, then make your choices about which tasks to do at the beginning of each time box.

My sense of overwhelm and anxiety has greatly diminished since taking this approach, and if your to-do list looks anything like mine, it's certainly worth a shot.

Falling to Systems

The sweet release of bird's eye planning