For most of my career, I’ve worked on several projects simultaneously at any given time. This means lots of information coming and going from and to different people, keeping track of documents and commitments, scheduling meetings, etc. Most of it happens on my computer, which for almost twenty years has been a laptop. (Meaning: it comes with me.) In the past few years, more mobile devices (e.g., iPhone, iPad) have also joined my toolkit. There’s a lot of things going on in these information environments. Keeping everything organized impacts my effectiveness; the time I spend looking for stuff isn’t valuable to my clients. Early on I realized that the only way I’d be able to do this would be if I developed organization systems, and stuck to them over time.

For example, I always have a “projects” folder on my computer. Each project I take on gets an individual subfolder in there. These folders use consistent naming schemes. These days it’s usually the client name, followed by a dash, followed by a (brief!) unique project name. Why not per-client folders? At one point I realized I had to strike a balance between depth and breadth. Going n-folders deep often meant not locating things as quickly. Of course, over time this folder can get crowded. Eventually, I determined the projects folder only needed to contain active projects; I set up a separate “archive” folder where I moved completed project folders.

This system works well for project documents, but that’s not the only information I deal with in my projects. I must also communicate with people. This entails using email apps, messaging clients, contacts lists, calendars, etc. I make commitments to these people (and to myself), and need ways to track those commitments. I’d love it if my computer had a “project mode” I could enter that would focus all of this information on a per-project basis. I’d only see the notes related to the project, the contacts for that project, the email for that project, etc.

There was a stretch in my career when I used an app that implemented this functionality, to a degree: Microsoft’s Entourage. Entourage was part of MS Office for the Mac, a replacement for MS Outlook. The two apps had some similarities; like Outlook, Entourage also offered unified access to email, contacts, calendar, to-dos, and notes. Unlike Outlook, however, Entourage offered a “Projects” tab that allowed me to filter information per-project. When operating in this mode, I could look at notes, emails, contacts, to-dos, and appointments for particular projects. I could also link a folder in the computer’s file system to the project inside Entourage, so was always one click away from all the other project documents.

This setup was close to ideal for me. Alas, it also had drawbacks. For one thing, it wasn’t easy to sync project contexts between multiple devices. This wasn’t an issue when I was using just one computer, but it became an issue as phones started growing more capable. However, the biggest challenge with the project tab in Entourage is that it required a lot of maintenance work. If a new person joined the project, I had to set up the contact in the project. While there was some automation around tagging email per-project, it wasn’t perfect. The most natural thing to do here would be to tag all emails coming from one person as belonging to one project. However, sometimes I’d be working on a couple of projects with the same people. As a result, I’d end up having to do lots of per-email tagging to keep things organized. This created lots of overhead.

Eventually, Microsoft discontinued Entourage in favor of Outlook for the Mac. Outlook was an improvement in many ways. Alas, the Project tab didn’t make the cut. At this point, I migrated to Apple’s detail Mail, Contacts, and Calendar apps, with OmniFocus thrown into the mix for task management. Instead of a monolithic app like Outlook, the default Mac apps follow the Unix “small pieces loosely joined” philosophy. This makes them much better for their intended tasks, but worse at keeping per-project focus.

Even with all the additional work it required, I loved working with Entourage. The ability to create rich contexts that encouraged focus allowed me to juggle projects more effectively and made me more productive. I wonder what a modern take on this concept would be like, given today’s more cloud-centric, AI-powered information environments. Such a system would surely be better at keeping things tidy without requiring so much input from the user, and sync between various devices. I’d love to try something like that—especially if it worked as a filtering layer over the apps I already use.