What to do when you don’t feel like working

Hamilton Chan
5 min readOct 15, 2020

When my kids asked me over the weekend how much work I had to do, I answered: “Infinite. I have an infinite number of things to do.”

That is in direct contrast to their homework, which is very much finite.

Unsatisfied, my kids followed up with: “But how many hours total will it require?”

My answer: “Still infinite.”

No wonder I get lazy over the weekends and end up sitting at my desk, consuming news over the internet, but somehow steadfastly refusing to make any progress on my work.

This is the plight of the modern day knowledge worker. Whether you are a corporate attorney, a writer, an entrepreneur or any other worker who makes a living via a laptop, the runway for your work extends over an infinite expanse.

You will never be done! No amount of work will ever get you closer to the end, because there are always more things you can do!

If you’re an entrepreneur, you could work on the vision statement for your company. You could help create new digital ads, for which you could create new content, for which you could Photoshop new images or cut up some new video edits. You could A/B test additional campaigns. You could check out last week’s web analytics. You could install better trackers and coalesce your data through Segment. You could also go for a run and get in better shape. You could learn a new recipe. You could wash some dishes. You could clean up the papers that have sat on your desk for months. You could text a friend. You could email a new prospect or set up a new marketing automation campaign. You could network via LinkedIn. You could read more news, and you could certainly buy more tech gadgetry to soothe the pain from your interminable To Do list, which you could decide to host on Todoist instead of Pivotal Tracker or Trello. Oh my, the list is indeed infinite!

Objectively, you know that everything you get done does represent forward progress. A jogger may have infinite miles ahead of them, but each run logged in a given day per week is a notch towards improved stamina and greater fitness.

We procrastinate on our infinite work because of infinite reasons. We procrastinate because of our own unreasonably high expectations, because it’s not pleasant to do the work, because we just don’t feel like it. But really all the reasons boil down to one: we procrastinate because we do not anticipate reward.

As fatally myopic animals, it is intensely difficult for us to value the rewards of tomorrow over the rewards of today. We are emotional beings, and want what we want today.

So what do you do when you don’t feel like working?

First, write about it. Vent. Complain. Put together a blog post! :)

Why? Because in doing so, you are at the very least doing something creative. You are creating. You are putting words on the page. You are not being passive, you are activating your finger muscles and your prefrontal cortex. Your limbic system is getting a break. Write. And journal. It will be a release from the prison of your mind to eke out some content and let it spill and soak onto the page. Your neuroticism will no longer be trapped in your head, and will fatigue itself in the blaring light of the public world.

Second, get a small win at all costs. Maybe it means clearing one piece of useless paper from your desk. Just file one thing. Treat it like getting 1 yard on a play in football when you’re 4th-and-1. Stick your cleat into the ground, gnash your teeth into your mouthguard, lower your helmet, and drive forward as if your entire being depended on it. You must claim those few inches at all cost.

In fact, I will do the very same thing right now. My desk is a mess, and I will file away some papers.

And… done! I just took about 10 to 15 minutes to sort through dusty old papers on my desk, and I feel much better. Small win … check!

Buoyed by the small win, what other small wins can I make? (Admittedly, I am midway through watching a Rams football game, which I paused only so that I could fast-forward through the commercials later. You can see why all of my metaphors relate to football).

Ah, I need to deposit a check. Let me finally figure out for the first time in forever how to do that on my phone.

And … I am not kidding, I literally just did this.

Phew! Just accomplished 2 tasks that I’ve been procrastinating on for months.

So great — I’ve proven that, motivated by the desire to write a blog post about procrastination, I can notch two 3-yard carries in 20 minutes. But how repeatable is this?

What about all the other monsters that sit in my To Do list, waiting to be slain? I just squashed a couple of annoying mosquitoes, but the big hairy high-impact meaningful and important work sit as steady as Stonehenge.

Easy! Now that you’re in a moderately productive mode, the coast is clear and you will be able to get more done. You’ve already sparked the most precious of all universal forces — momentum — and the rest of your To Do’s will acquiesce to your will.

Should you lose momentum, no worries. Reread and repeat these instructions: 1) Write out your frustrations, pushing you into creation mode; and 2) Gnash out a small win, no matter how small and no matter what it takes.

With any luck, you will rekindle within yourself the joy of getting work done.

My view still stands that the work ahead of me is essentially infinite, but the work behind me — my accomplishments and my creations — are very much finite and quantifiable.

And that is the only way to look at it.

--

--