My State of 2019 – Personal Productivity

Mmmm, personal productivity and personal productivity systems, some of my favorite things! I can’t tell you the number of hours I’ve spent over the last 10 years playing around with todo list apps, document management, note taking apps, etc. I feel like if it was released for Mac or iOS I’ve used it. I’ve also found that I’ve spent far more time messing with my “system” vs. actually using it to get things done.

Part of what I wanted to accomplish in 2019 was settling on something and using those tools to get work done. I was partially successful but moving forward into 2020 I want to finally settle down with a set of tools and not spend anymore brain power thinking about tools and systems and spend my time actually doing the things I need to do.

There are a ton of apps out there to help you manage just about every part of what would typically be a productivity system. On the Mac users have been blessed with a ton of great choices. Let’s talk quickly about todo list apps.

Todo apps

The big names in this space are Things by Cultured Code, OmniFocus by the OmniGroup, and Todoist.


OmniFocus is definitely for power users. I used it for years but spent more time trying to figure out how to configure and maintain it. At the time OmniFocus also had terrible recurring date support. I recently gave OmniFocus a spin and that has since been fixed and it might have the most options of any app I’ve tried. But it again proved to be too much for my needs and it is still on the expensive side.


I tried Todoist in the past because it was multiplatform. As a web app it’s accessible anywhere you’ve got a browser. It has a nice set of features and a Teams version if you need collaboration capabilities. Unfortunately it doesn’t support start and due dates and just didn’t fit my needs.


I finally settled on Things 3. It has a beautiful interface and has the right mix of features I find useful day to day. Here is why I like it:

  • Pleasant user interface
  • Very good recurring task support (things like ‘3rd Friday of every month’)
  • Items can be dragged into any order you want in the lists
  • Today view has a “This Evening” subsection that is useful for separating out daytime tasks vs. night.
  • Headings in projects. This is a great way to break a project down into sections
  • Rock solid sync

Some people think Things is too simple and I’d argue those people really haven’t given it a proper look. It definitely has an opinionated way about it but it works well for me. I plan on writing later about the system I’ve come up with in Things for managing tasks that finally works for me. It’s the system I’ll be using moving forward into 2020.

Document Management and Notes

Another area where I have spent countless hours playing with different applications and systems is how to store important documents and notes. For the longest time I was using DEVONthink 2 Pro edition to store everything; notes, important documents, the works.

Then at some point I stopped doing that and just dumped everything into a set of folders on Google Drive. I did that because I wasn’t really using DEVONthink for much more than a dumping ground and wasn’t really using any of its power features. My documents were also “locked” into this proprietary software. The folder system worked fine as Google Drive indexes all of the files for search-ability. Then I became concerned about privacy because, well, it’s Google. I also ran into a problem with access, I couldn’t get to Google Drive from work. So I moved that set of folders into Microsoft OneDrive because I was already paying for a personal license for Office 365 and I could get to OneDrive from work because we use Office 365 there as well.

At that time I also split off notes from documents. Scanned receipts, medical information, etc. was kept in the folder structure on OneDrive but I moved all of my text notes for work and personal use into a repository at GitLab. It was free, versioning was easy, sync was simple, and I could get to it from absolutely everywhere including work. I was using the Visual Studio Code text editor to edit my notes, which I write in Markdown.

Then Bear came along and I fell in love with that application (are we seeing a pattern here?). Bear has a great UI and a wonderful set of features. If you want sync however you have to pay for a yearly subscription. I did and I enjoyed Bear a lot but the major problem with Bear is that it uses iCloud for syncing documents and that is another system that is blocked at work. I’ve been dealing with that situation by various means up until recently when it was getting close to my Bear subscription ending. I have been wanting to get rid of as many subscriptions as possible and Bear was one that I could easily get rid of without feeling too much pain. But it wasn’t just the subscription that lead me off of Bear.

For various reasons I decided that I really just want my important documents kept locally. It was clear to me, after a bit of thought, that I don’t need access to them from everywhere and from a security standpoint there is less to worry about.

From a notes perspective I generally have notes in one of two categories: daily notes and notes related to software development. For my daily notes I’ve decided to use the app Agenda. Its on iOS and Mac and its designed for time-based notes. I still have the problem with iCloud syncing but I can manage that in the same way I was using Bear.

For my software development notes I’ve turned to a tool designed explicitly for that purpose: SnippetsLab. SnippetsLab supports Markdown, supports creating GitHub gists from snippets, and can sync with iCloud or just about any other sync solution.

For everything else? I’m back at DEVONthink. It turned out that being locked into a proprietary application wasn’t all that big of a deal because when I moved everything out it was a simple matter of exporting the files. DEVONthink 3 was recently released and that was a major upgrade. They also made the upgrade available at a pretty substantial discount during the holidays so I bought that and decided that was going to be my tool moving forward.

Moving forward into 2020 I plan on keeping that system in place and working with it.

Cloud Storage

The last area I have spent considerable time, expense, brain power, and worry over is cloud storage. I’ve used them all, and switched back and forth time after time. My latest turn was with Dropbox and I’ve found Dropbox to both be really expensive and the best by far of the major sync solutions. But as part of looking over 2019 and with the planned theme for 2020 of stability I took a hard look at do I really need any cloud storage?

Yes I do need some but most of what I sync needs to be through iCloud which I’m already paying for at the 200gb tier. My Windows sync needs are actually met with iCloud as well because Apple recently rewrote the iCloud application for Windows to use OneDrive’s file-on-demand feature. My Office 365 subscription gives me 1TB of cloud space in OneDrive but I’ve decided to drop that because I never use the Office 365 applications and the OneDrive client on the Mac is terrible.

Google Drive isn’t even a consideration. Unless you pay for a G Suite business account you can’t get an on-demand files feature.

That leaves Dropbox and I almost paid for a year. As noted before their sync client is excellent. I like the new desktop application they introduced recently, and Dropbox Paper is a great notes system. At the end of the day though I don’t need to store anything there. It’s completely pointless to spend the money without a need greater than being a tech geek and wanting a Dropbox Plus account.

So, for 2020 the plan is to settle on iCloud for all of my cloud storage needs. Things will handle my tasks as it has been doing so ably. DEVONthink, Agenda, and SnippetsLab will handle my document and notes needs.

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