The silly thing I do to conquer my most dreaded work

One step at a time. (Image by János Bencs)

One step at a time. (Image by János Bencs)

For years, I was obsessed with getting to Inbox Zero on my email (meaning that I had dealt with every email in my inbox, leaving it completely empty), so much so that I would often spend four to six hours engaging with email in a single day.

I got incredibly fast and efficient at dealing with email, but email became my entire job. I needed more people on my team. I corrected that problem, and sometime in the fall of 2018 I let go of email as a measure of my productivity. The result was this blog, three new projects, and a new career. Not bad.

In the meantime, the emails in my inbox piled up, since they were no longer my focus. It cost me—I missed out on opportunities and relationships and enjoyed many a late fee. I acknowledged that I couldn’t ignore electronic communication altogether, so I would “triage” my email on a daily basis while less urgent emails accumulated, and then clean out the inbox completely in longer sessions every few weeks.

More recently, I’ve set the intention of doing this “clean out” on a weekly basis instead of whenever I get around to it. Otherwise, the deferred decisions become overwhelming and exhausting. But how do I overcome my resistance to what is still a challenging task?

The answer is very silly, and it totally works. You are welcome to steal it. It is designed to accommodate the vagaries of what my friend David calls a “Creative Divergent Mind” (which is a positive way of framing the challenges and gifts of ADHD).

Here’s what I do:

I add up the number of emails I need to process (i.e., make decisions on and respond to) across my three work-related accounts.

I then add several tasks to my to-do list based on the number of emails. For example, if there are 50 emails, it might look like this:

  • Process 20 emails (10 minutes)

  • Process 10 emails (10 minutes)

  • Process 5 emails (5 minutes)

  • Process 5 emails (10 minutes)

  • Process 5 emails (10 minutes)

  • Process 5 emails (10 minutes)

As you can see, I’ve made the fifty emails into six tasks, with an estimate of how long each set of emails will take to read, make decisions on, respond to, and so on.

The different time estimates take into account not only the fact that some emails are quick to deal with, but also the fact that decision-making gets harder and slower as you go. There’s something about acknowledging and honoring this fact that lowers my resistance to the task.

There is a gamified aspect to this work as I check off each set of emails and try to come in under the time estimate. However, I’m often gratified instead of frustrated when I go over the time estimate. When it takes me 22 minutes instead of ten to write thoughtful responses to a set of five emails, I can say to myself, “See? See how hard this is and how long it takes? No wonder I had put this off until now.”

There are some tasks that make me feel like I can’t handle another minute of this, a pain that is almost physical. I’d liken it to sitting in the middle seat of an airplane at 2 AM on a redeye flight, unable to sleep, trapped, hungry, and needing to pee. It’s a moment of such discomfort that if you had a poorly functioning limbic system (or were a toddler), you’d stand up and scream.

And yet, most of the things I have to do, I signed up for and can do under the right circumstances. The multi-task approach to my email minimizes the discomfort and overwhelm. The work becomes manageable when divided into tiny bite-sized pieces. I can celebrate tiny milestones of progress and experience the hope of release.

I’m not too proud to treat myself like a toddler if it gets the job done. And like a toddler who balks at a new food that later becomes a favorite, I might even enjoy the work once I get into it. I swear by this silly method for conquering my email. It doesn’t matter how granular I had to get to do the work if I end up feeling proud of what I accomplished.

Let me know how it goes if you try it.