This is a miscellaneous list of things I feel like I got better at in 2016 and hope to build on even more next year. Also see part 2 on time and project management.

Regulator expressions

Maybe just through sheer resolve, I finally got better at writing regulator expressions in 2016. If you work with text files in any capacity, learning regular expressions is well worth your time. They are so much more efficient than writing loops in scripts to clean up text files, and they really take ad hoc “find/replace” fixes to the next level in text editors like Sublime Text.

There are infinite practical use cases for regular expressions if you can punch through their opaque syntax. For example, I can search for all hyphens that occur at the beginning of a line if I want to manipulate the indentation of a Markdown list.


I continued to increase my time investment in Python, which has become my all-purpose programming language for manipulating large numbers of text files and even leveraging Terminal commands. There is something that’s just very friendly and universal about Python, and it’s cross-platform support makes me believe that the time I put into it today will continue to payoff for a very long time—even in a possible future where macOS and its Apple-centric scripting languages fade away.


2016 was the year I finally parted with Evernote, and I couldn’t be happier with my decision to go all-in on DEVONthink Pro Office. I’ve been able to bring all of my content management under a single roof and enjoy the unrivaled organization tools, search operators, OCR, and security that DEVONthink offers. If you are a macOS/iOS person, I can’t recommend DEVONthink products enough.

As 2016 draws to a close, and I begin organizing tax season information, it’s hard to believe I used to manage tax docs offline because I didn’t trust Evernote’s cloud storage. Now everything is securely accessible on my Mac, iPhone, and iPad.

Static blogging

I left SquareSpace for Jekyll in 2016. Eight months later, I still love the concept of a static website and the flexibility it’s given to my writing workflow on both the Mac and iOS. I also learned so much in the process of converting my blogging setup to Jekyll—Python tricks, etc. It was a great move, and I love the independence of having my own site, even if it’s just a small flicker of light compared to the social/aggregator sites that many think “killed” blogging. They haven’t killed this one.

Long live the GIF!

This year, I realized that the latest version of ScreenFlow lets you make GIFs. It’s simply another export option. GIFs take almost no time to create and are so much better for showing someone how to do something when you want an animated image but don’t need audio. If a screenshot is worth a thousand words, a good GIF is worth a thousand follow-up questions that don’t have to be asked.

Miscellaneous Mac tips

Sometimes the small, barely noteworthy adjustments to workflows make the biggest cumulative difference.

  • I learned that I can change the default folder for screenshots from the Desktop folder to Downloads (or any folder). My Downloads folder is an all purpose inbox that gets regularly cleaned by Hazel. It’s also easier to drag temporary files from the fan view of my Downloads folder in my dock than it is to show the Desktop.
  • I started using “All my files” in the Finder to quickly locate recently modified files for uploading in web forms, or to locate a file I accidentally saved in the wrong place on my Mac. The “All my files” search folder has been there forever. For some reason, I started taking advantage of it just a few months ago. It’s also a simple reminder of just how powerful the Mac filesystem itself is as a content management system.
  • I (surprisingly) embraced Siri on the Mac: “Show me keynote files I had open yesterday” and similar commands work flawlessly. Speaking really specific commands like that is much more efficient than doing custom Spotlight searches.
  • I moved to PDF Expert for almost all PDF editing and annotation tasks for two main reasons: 1) PDF Expert has gotten really good at the things I do to/with PDFs on a regular basis and 2) in macOS Sierra can no longer be trusted not to break PDFs.