My Digital Productivity System for 2023

This is one part of a multi-part series on how I get things done.

While I have always loved pen and paper there are a few areas where digital tools bring a unique value; scheduling and documents.

As a director of engineering, my days are calendar driven. While the allure of a paper-based calendar is strong it is ultimately impractical for my needs. And, once I have a digital calendar in my tool belt, it becomes convenient to use for anything that has a date attached to it.

While there are paper-based alternatives for scheduling, files are digital now. I spent a high school summer printing digital patient records to revert a doctor’s office to paper charts. A little part of me died that summer; no one should repeat that experience.

And, of course, there is the intersection of these two areas; meetings. My workflow there is detailed enough to deserve its own section which we will get into below. Let’s dive in.

Scheduling

Setting meetings aside, there are a variety of scheduling needs for tasks that are worth considering.

First, there are time-sensitive tasks, anything that must happen at a specific date and time. For instance, putting the Thanksgiving turkey into the brine. These are nearly the same as an actual meeting but without the duration. Digital calendars excel here, primarily for their notifications that ensure you don’t forget these important items.

Second, there are recurring tasks, anything that happens on a regular cadence. From weekly reviews to chores around the house, I have several reminders at a variety of cadences to drive my productivity routines. These aren’t as time-sensitive but are a critical part of externalizing tasks to clear your head.

Third, there are future tasks, anything that doesn’t need to happen this week. If I have a task due next month I’ll add a reminder the week before to my calendar. This helps me remove clutter from my analog system and when the task pops back up I file it back into that system.

Finally, there are “time blocking” tasks. With time blocking, you schedule your tasks directly on your calendar, like a meeting, as opposed to working from a to-do list and fitting tasks around your other commitments. In this situation, the scheduling isn’t driven by a deadline, but by making deliberate use of your time. I don’t use this often but when I have a hard deadline approaching or I’m juggling too many things I will pull in this tool to help.

My tool of choice for the first three use cases is Google reminders. With the Google ecosystem, there are annoyingly too many different ways to put tasks on your calendar; from reminders, to tasks, to scheduled keep notes. I have landed on reminders since they are the simplest option of the bunch, though I do cheat with scheduled keep notes when I need a checklist for recurring tasks like my weekly reviews. For time blocking I just use Google Calendar, just like I do for meetings below.

Documents

My earliest attempts at digital document management were beautiful, bespoke, hand-crafted folder structures. The organizational compulsions took great joy in finding just the right taxonomy to bring order to the chaos. As the volume of documents grew, it became clear that tending to my documents was a net negative on my productivity. That is when I came across Tiago Forte’s PARA approach to managing digital documents. I was skeptical at first, I so loved the structure I had built, but after a trial run, I knew I was never going back.

The PARA system organizes documents based on their actionability rather than their content as most other systems do. This shift turns your documents into tools for productivity. At its core, the system contains four top-level folders (one for each letter of PARA) and recommends no more than four folders deep. This keeps the structure manageable; easy to navigate and easy to fit in your head.

Projects: The folders here map nearly one-to-one with the projects in my analog system. Mirroring your document and task management systems is a powerful practice. I can quickly find anything I need for the projects I’m working on. I can even use this structure to park projects that are on hold by removing them from my analog system and then pulling them back from here as needed.

Areas: The folders in here map to broader scopes that don’t have a specific deliverable but still require regular focus. I have folders here for each of the teams I support, for committees and boards I sit on, and for key relationships I maintain.

Resources: The folders here capture documents I refer to as needed rather than regularly. Good examples are recipes, headshots for online profiles, information on DnD which I’m learning to play with my son, zoom backgrounds, and so on.

Archive: The folders in here have fallen out of use in any of the other folders. The bulk of these are completed projects but there are folders for areas like previous jobs and resources I no longer refer to (my Covid folder!).

In each document product I use (Dropbox, GDrive, Quip, etc.) I have these five top-level folders keeping a very consistent and familiar look and feel wherever I am.

0 Inbox 
1 Projects 
2 Areas 
3 Resources 
4 Archive

You’ll notice I’ve added one more folder named Inbox. This is a convenient dumping ground for automatic capture. To the extent possible, I try to automate capturing any files that cross my eyes. If I download a file on my phone Autosync will automatically add it here. If I scan something using SwiftScan it will end up here. And if someone sends me an email attachment Zapier will send it here. I review these files weekly and while I discard 80% of them it makes keeping the valuable 20% mindlessly easy. Having that project file from that email you received 6 months ago at your fingertips has saved my butt more than a few times.

Meetings

Meetings are where scheduling and documents cross over. The reason for this is almost every meeting I attend has an associated shared document.

Most of my meetings are reoccurring ones with a variety of different groups of people. This could be a 1–1 meeting with someone who reports to me, a peer group or team meeting, or an external meeting with a contractor. The shared document creates a running log of what we have discussed in the past and forms a holding area for topics we need to discuss in the future.

Having these meeting documents is another way I can reduce the clutter in my analog system. A purely analog option would suffer from the personal nature of pen and paper. A collaborative document allows everyone in the meeting to jointly own the agenda.

Google Calendar is my tool of choice here. Others swear by flashy calendar apps but Google Calendar does everything I need. More importantly, as one of the most popular calendar apps out there, most 3rd party tools like Zoom integrate with it. In particular, it works with Clockwise, the automated calendar manager you need but didn’t know existed. It will optimize your free time, move conflicting meetings, block off time for events on your personal calendar, schedule lunch blocks for you, and more. I can’t imagine working without it anymore.

Ubiquitous Capture

Finally, there is one more minor but valuable component of my digital productivity system; the ability to capture an idea or task at any time wherever I am. Before smartphones, I was rather proud to wander around with a small notepad and a pen wherever I went but those days are unfortunately behind me. The reality is I do always have my phone in my pocket and I’d rather keep my daily carry to an absolute minimum.

There are several options in this space but I went with TickTick, the simplest option I could find that had excellent quick capture options. It has very nice global shortcuts on Mac and quick-add shortcuts on Android. It is heavily customizable which I like only because it allows me to turn off and hide almost everything, turning it into a simple capture tool. Tasks and items that land there get quickly moved into another system the next time I’m at my desk.

Keep It Simple

My focus with this system is simplicity. It doesn’t include power user tools for personal knowledge bases or networked note-taking. By using a few, core tools, I can flex to any environment. Each new job comes with a new set of company-approved tools and I’m able to fit my workflow to the applications at hand given a place to store documents and a calendar for tasks and events.

There isn’t one best productivity system to rule them all but I would encourage you to give this a shot. If it feels too constrained and too simplistic, perhaps that is a sign that you are juggling too much and some constraints would be helpful. If it feels too complicated, I’d love to learn ways to simplify the system without losing the core benefits.