This one rule strips 90% of chaos out of my day

As a productivity nerd, I spent years honing my task management system so that I never missed a thing, but despite all my organization, I'd still find myself scrambling to prepare for a meeting or losing track of my top tasks once my day began and the chaos began creeping in.

All that changed when I stumbled onto a new rule for my to-do list, which led to a new practice that's been a complete game changer for keeping chaos at bay. In this post, I’ll get into how it works.

How the die was cast

Do you ever look back and realize where your habits started? When it comes to how I work, I can trace things back October 2014. I had recently joined the management ranks at a large healthcare consulting company, and I was in my second year of an MBA program that gobbled up my nights and weekends.

Managing a team and being in a client facing role meant that my days were often chaotic. Each morning my inbox would be filled with emails that often needed a response, and my calendar was always at least 50% full of meetings that I had an active role in.

More often than not, I felt like I was just trying to keep up with whatever the day was going to throw at me. Inbox zero was a rare treat when I could achieve it, and my to-do list was always brimming with dozens of tasks that had to get done in the near future.

Believe it or not, I had been a strong adherent to David Allen's Getting Things Done productivity system, but it still didn't feel like it enough. I'd find myself scrambling to prepare for a meeting that was less than an hour away, or pushing back a really important task after getting dragged into the weeds on some other project that wasn't in my plans.

Over the next nine years, I'd have many other jobs at many other companies, but this way of working didn't really change much. It wasn't until I found myself on sabbatical that a new pattern finally emerged.

The experiment

For the first time in my professional life, I found that I got to choose what to spend my day doing. Despite all that freedom however, my to-do list still felt overwhelming. With no meetings or deadlines to govern my attention, how could I still be feeling overwhelmed?

After a bit of reflection, I realized that my problem came down to two issues: The menu of choice was too long, and I didn't look at it often enough.

For years I would mostly stick to a weekly review where I'd budget a couple of hours to assess the 50-60 active projects I had going on at any given time. After finishing this review however, anytime I'd pull up my to-do list, I'd be faced with a wall of over 40 tasks that I could do, interspersed with a handful of tasks that had to be done.

It took me a while to realize that my eyes would simply glaze over when I saw a list that long. So I decided to try an experiment.

I'd resolve to keep my to-do list to 20 tasks or less on any given day. During my weekly review, I'd pause the majority of my projects so that only 10 or 12 were active at any given time. The result was a short menu of available tasks that most importantly, felt manageable.

By keeping the list short, I found that I'd rip through the actions much faster, and enjoy that infectious feeling of progress and momentum as I checked items items off the list. Crossing an item off a small list feels like a much bigger step forward than shaving off a task a huge list, and there's nothing quite like the feeling of clearing the whole list for the day.

I also found myself looking at that dwindling list several times a day instead of once a week, which meant that I always had a line of sight into the day's most important tasks, which helped me say no to competing demands with more confidence.

By keeping up the weekly review, I was still reviewing all projects, active or not, which helped thwart the anxiety of missing something important that was suppressed from my daily short list.

The lightweight nature of the short list led to a new ritual. Each morning I'd spend maybe five minutes reviewing my short list and making decisions about which of these limited tasks were most important, and which might be better saved for another day. Then I'd get to work.

The most surprising thing that came from this experiment is that the morning ritual still ended up being very helpful even after I reentered the workforce.

An unexpected benefit

Even though I'm back to a knowledge working role with a hyperactive Slack culture and dozens of demands coming at me at all hours, I still protect that first hour of each morning to set the day.

I treat it like a pre-flight check to ensure I cover all my most important bases before I settle into deep work. My morning ritual now includes reviewing my calendar and quickly preparing for any meetings I have coming up, balancing my checkbook, screening email and slack for action items, and then most importantly, reviewing my short list and selecting which tasks need to be prioritized for the rest of the day.

Completing this morning ritual takes anywhere from 30 minutes to an hour, depending on how much new activity is needed to review in slack or email. Once I'm done, I have a clear idea of what my day needs to look like, I'm ready for each meeting I have coming, and most importantly, I don't feel like I'm constantly trying to just keep up.

Calmer seas

Keeping my to do list short allowed me to create a sustainable morning ritual that in effect is a compounding system. Clearing my head of all but a handful of items allows me to get things done faster, which allows me to build on top of completed work sooner, allowing me to get more done in a shorter amount of time, even when the environment is noisier than ever.

Setting the day is fantastic for figuring out what the next eight or so hours need to look like, but if you can fill that remaining time executing or building a compounding system, the sky's the limit.

In case you’d like to see a spoken version of this essay, be sure to check out this post on YouTube.