Why You Should Do More of What You Dread

Do you think you do your best at the job tasks you enjoy most?

If you’re like me, if you’re like my team, probably not. Your breakout moments — the ones where you solve a huge problem or strengthen a relationship or convince a holdout — probably come from facing a problem that you dread.

The moral of this story is NOT: “so everyone should try new things! Break out of your comfort zone! Rah-rah!”

The moral is — wait, let’s look at why. Why are people often more effective when they’re facing down dreaded challenges?

  • Clarity. Most people are better at articulating negatives than positives. This means you start out a dread project with a clearer sense of what you’re actually trying to do. Editing is easier than writing; pushing back against something specific is easier than not having constraints.
  • Optimization. Who wants to spend more time doing what they dislike? You’ll naturally gravitate towards fast and imprecise methods, which are often the best way to make progress quickly against the things that matter most.
  • Lower standards. Wait, this is a good thing? Well, yes — lots of knowledge workers take so much pride in their work that they set too high of standards for themselves. Those standards cause you stress and push you towards tried-and-true methods vs. experimentation.
  • Focus on “done”. This is related to “lower standards” — when you have a dreaded task, you’re just looking forward to the moment when you can cross it off your list. Fun tasks, you don’t necessarily want to end. Even at a subconscious level, you’re probably postponing that moment of completion in favor of more fun noodling/iterating.

Hopefully seeing these articulated will spur you to stop procrastinating and tackle a dreaded task today. (or try to apply this type of thinking to a ‘fun’ task).

(Note: when I say “work you dread”, I don’t mean work that is soul-deadening or meaningless or rote. That kind of work is bad for everyone. As a manager, a big part of your job is reducing the amount of that your team is exposed to; as an individual contributor your job is to let your manager know when you’re being burdened with it.)