How do you handle boring and repetitive tasks?

TextExpander Talk
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Long ago in another life, I worked a job that required a lot of data entry, mostly filling out forms for alcohol licensing. We had forms for state, city, and local jurisdictions. Most of them asked for the same information over and over, but we still had to fill them out by hand because they were all slightly different.

It wasn’t the most fun job in the world, but as Don Draper said, “That’s what the money is for.” However, I had a couple of tricks for making it more tolerable:

  • Audiobooks and Podcasts: This is one of the main ways I kept myself sane. I also had a long commute, so I listened to so many books and podcasts while I was working this job. At the time, I was listening to a lot of tech podcasts like This Week in Tech, which is where I first learned about TextExpander.

  • Text snippets: I was in a typical Windows-only corporate office, and unfortunately, this was years before TextExpander was available on Windows, so I had to use another tool. I so wish we had the type of organization Snippet sharing TextExpander now offers. I had to manually recruit people who were interested in automating the work, set them up with the tool (bypassing IT to do so), and bring over the Snippets on a thumb drive.

Some of the information was different for each form, but much of it was reusable like:

  • The names of our business entities
  • Our corporate headquarters address
  • Our corporate phone number
  • Officer names

Even with only a few of us using text snippets, it probably saved that department hundreds of hours (whether IT liked it or not).

How do you make repetitive tasks more efficient or at least tolerable?

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How we frame the “boring” parts of our jobs can make a huge difference in how we approach them.

I had a real lightbulb moment after listening to a podcast on The Benefits of Boring. It got me thinking about how the tasks we often find tedious are frequently the essential actions that underpin success and keep the wheels turning.

This really resonated when I returned to an engineering role last year. You tend to forget the less glamorous bits when you’re away! Suddenly, I was back to doing regular code reviews, managing my local build environment, dealing with the CI/CD pipeline, and updating packages.

Sitting down after hearing that podcast, I realized those were my “borings.” They weren’t necessarily the most fun or creative parts of the job, but they are absolutely critical for building quality software, maintaining stability, and ultimately, keeping the business moving forward.

Just shifting my mindset around these tasks – seeing them as foundational rather than just chores – had a surprisingly big impact. I found I stopped avoiding them or putting them off. I started tackling them more consistently, approaching them with a better understanding of their importance, maybe even a little more willingness or ‘joy’.

I found that documenting my workflows has been helpful, it gives a baseline to think about optimization. Maybe even use a GenAI tool to find ways to improve the workflow.

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