Obstacles to automating my workflow

I’ve always been intrigued (obsessed with?) software that automates small chunks of my daily workflow.

TextExpander on the Mac and ActiveWords on Windows can generate big chunks of text from a few keystrokes. I can generate a standard response to a student question or directions to my office or just today’s date by typing a few characters.

Macro programs like Keyboard Maestro (Mac) can automate more complex sequences like automatically opening several applications and executing some menu commands in each. When I found myself needing to manually copy data from a spreadsheet into fields on a webpage I was able to use Keyboard Maestro to automate the copying, switching applications, tabbing through fields, and pasting in text to make the process bearable.

Scripting tools like AppleScript and
Automator (Mac) or AutoIt and AutoHotkey (Windows) can allow such automations to be tightly controlled using a programming language. Automator in particular makes it very easy to quickly automate something like combining multiple pdfs into one big document or resizing a bunch of images.

I have played with these programs with varying degrees of success but I find several obstacles to gaining the benefits from these tools:

1. Taking the time and carving out the mental space to identify what can be automated. Most of the time I focus on doing whatever needs to be done. In the heat of the moment I need to put my full attention on the doing; its hard to step back and notice patterns that can be automated.

2. Taking the time and energy to set up the automations. Setting up a shortcut for my name or address or a frequently repeated phrase is easy. Setting up a macro to move data out of one program and into another can be quite involved. Doing that kind of meta-work can be very appealing, especially when I am looking to escape doing the actual work in favor of the fun and challenge of setting up a new system for (eventually) doing that work more efficiently. Typically what draws me in is not the many high-yield but unexciting automations but the intriguing ones that can soak up a lot of time with little to show for it. So I have the experience repeatedly that meta-work is not the huge productivity booster I want to convince myself it is, and I wind up leaving undone the many little tweaks that would have a big impact.

3. Training myself to actually use the shortcuts. It takes effort to learn these shortcuts. The ones I use all the time are easier to learn because the next opportunity to practice the shortcut comes up quickly. Such is the case with shortcuts for my name, phone numbers, email addresses, the date, and the time. I have enough opportunity to type these on a daily basis that it is easy to develop new habits. On the other hand I have shortcuts for words I use a lot in my writing, to save some time typing, but some of these I just don’t use often enough to reach the critical threshold of having them set in my mind. In a sense, setting up automations and shortcuts is like creating my own private language for doing my work. I then have to learn this new language and gain fluency with it.

Taken together the obstacles above mean that there are some opportunities for streamlining my work that I should be taking advantage of, but don’t. In future posts I hope to explore how to tap some of these opportunities as well as some of the non-obvious benefits of this kind of automation.