Stack of documents with binder clips and pen on wooden table, closeup view

3 questions I ask when planning in uncertainty

I know you’re bombarded with tips that claim to unlock the one perfect way to work right now, I am too. Those articles and social media posts make it challenging for me to write about the topic. I cry BS on the snake oil cures of productivity. Life (and work) is a process, a journey that’s often messy, and it’s rarely one that follows a stable or straightforward path.

It is rare than anything I plan works out exactly how I thought when I made those plans. That’s true this year! It’s been an overwhelming one to the extreme — conflicting advice as to how to stay safe, sudden disruption to schedules and environments, grief, and loss.

The secret is that there is no one true way. Plans and your method for creating them will change and evolve over time. While it’s impossible to know with absolute certainty about the future, it’s also possible to find a way to move forward without an endless spiral into inaction and panic when things go sideways.

What can help is to create moments of stability and calm to give yourself the distance to evaluate and figure out what needs to change. Use the best tool you have to create the best plan you can knowing what you know at that time. Hindsight bias is a bitch, but don’t let it dictate your plans.

One way to do this is to schedule blocks of time for planning, review, and work. I like to have check-ins throughout my week and depending on how I feel work is going during the day. These are not involved or formal! I step back (ok, I roll my chair back from my desk) and ask myself the following 3 questions:

  1. Am I working on what I thought I would be right now?
  2. Is what I’m doing moving that task forward?
  3. Is something else bothering me and affecting my focus?

Time Blocks to Stay Focused

If something has preempted my schedule, I try to figure out why. Is it a case of “ooh shiny”? Often this happens after I check email and am distracted by something new that came in and disrupted what I was thinking about. To combat this, I set a timer/alarm for when I want to stop working on this unexpected task. I also make a note to reschedule what I’d originally planned. This is why I like time blocking. I have time set aside for different types of tasks (including checking email and messages on social media). They reduce what I term, squirrel mode, where I run around scrambling on different tasks.

Attention Residue and Next Action Tasks

When I shift focus on tasks, especially when I do so unplanned there’s often attention residue and my forward progress is muddied. The solution for this is to take a moment to write out with action verbs what I need to do to move the task forward.

Quick brain dumps

If other projects are trying to steal my attention, I pause and scribble out a quick brain dump of what’s cluttering my head to get them out and allow me to focus on the task at hand.


I hope that these three questions help you to plan and make revisions during times of uncertainty. Stay home (as much as you can) and socially distance. Wear a mask. Wash your hands.