I have a lot of projects in-play at any given time, which I think is an unavoidable by-product of being a solo designer with entrepreneurial aspirations. At the moment, I’m finding that my major challenge in managing those projects is not, as I’d presumed, being better organized with project documents. Instead, the limiting factor is the ease with which I can make a context switch. The easier it is for me to remember what I was last doing on a given project, the easier it is for me to make a bit of progress on it.

Managing Information versus Making Decisions

These days, I’m spending my time split between the home office, Starbucks, and my friend Sid’s photo studio. All of these locations are within 5 miles of each other, but there’s a lot of data that I need to bring with me. Fortunately, all three locations are now Internet-enabled, and I’ve been able to push most of what I need into the cloud:

• For consolidating project status, communications, and deliverables, I’m using a Basecamp Basic Plan for $24/month.
• For remembering events, I’m using Google Calendar tied in with my Google Apps for davidseah.com. Google Apps is also my mail handler and client.
• For synchronizing and backing-up my working files, I’m using a DropBox Pro 50GB plan for $99/year.
• The website is running on a Media Temple (dv) Rage 3.5 dedicated virtual server, which also manages a host of other websites, which is my main internet presence.

Now, all this stuff is just for holding data that is ready to be transformed into new data. Deciding what to do at any given moment is not handled by any of these systems. For that, I’ve used a combination of the Emergent Task Planner and a large notebook (my beloved Cachet Classic Graph hardcover) for “central dispatching” in the morning, but lately I’ve been dissatisfied with how it’s been working.

The biggest issue is working between three different locations, which means that I need to make sure I have my ETP and notebook with me in addition to whatever physical materials I need (books, cameras, laptop computer, etc). The inefficiency is that I have to check the notebook or ETP before I leave the house, which means taking it out of my crazy-full bag (and occasionally forgetting to repack it, which is a day-killer).

Moving Decision Making into the Cloud

So while I like my paper notebooks, I’m now trying something different: using a cloud-based To Do list application to maintain the “big picture” on ALL of my projects, and then opportunistically assigning time to them as it strikes me. In other words, I’m trying to create a constantly-changing buffet of benefit-producing opportunities.

After looking around for a bit, I settled on Wunderlist because it was available on all the platforms I use. Plus, it’s a cute little application. I have it start up automatically on both my desktop and my laptop, so I always have it running in the background. The synchronization features ensures that the lists are up-to-date on all my computers and devices.

Why Wunderlist?

I dislike the task / subtask model of task organization, which ruled out quite a few to-do list applications that use “Tree View”-style controls. Wunderlist, by comparison, uses a folder metaphor; you select the folder, and you see the contents within it. What I like about this is that you see one list at a time, which makes it easier to focus on what you want to get done right now. If you have a Tree View display, you have to manually scan the list to find the part you’re interested in EVERYTIME you are looking at the list. If you ask me, that undermines the effectiveness of a to-do list.

Wunderlist has a few other useful features, such as the ability to add a comment to a task and set a due date. It also has some rudimentary filtering ability so you can see what’s due tomorrow. While the user experience feels sort of like a late-90s Macromedia Director application, it appears to be working well enough for my needs.

The Current Setup

My main goals with regards to Wunderlist is three-fold:

• BEST OPPORTUNITY: To keep track of projects on spectrum of hi-yield possibilities
• CONTEXT SWITCHING: Remembering what I need to do next on a project, so I can pick it back up quickly
• PRIORITY QUEUE: Keep a working, maleable list of what I think is most important

Here’s a snapshot of Wunderlist to give you an idea of how I’m organizing it:

The most active list is the tracking inbox, which contains the things I’d like to get done in the next day or so. The most pressing items are at the top of the list, and the really critical ones are marked with a star. It is always sorted from most-important to least-important, and you always take the most-important element at the top of the list first. This is the “priority queue” I mentioned.

The rest of the lists are project folders, which contain step-by-step recipes for getting them done. For example, my “project: mailstation” folder has the following items:

• find a nice table for livingroom mail station
• find a main bin for “mail to be sorted”
• find a sort solution for 5-7 classes of mail
• find a way of handling oversize mail
• find a way of handling magazine/catalog storage

Here’s the contents of “Money: Products”:

• International amazon setup, check to see if it actually worked
• Overview of PCEO System (15 minutes)
• @staples to buy stamps, envelopes for fountain paper notebook sample kits
• Write blog post about sample kits
• Link ETP product SKUs on Amazon.com somehow
• Print gun safety poster

If it’s not clear, the idea behind these folders is to collect things to do that are related to a particular outcome. In the first example, this is the creation of a place to keep my paper mail so I can process it more efficiently; each of these tasks is an involved search-and-acquire task that requires me to visit a lot of furniture stores. I don’t want to buy a piece of junk furniture, afterall. The folders also allow me to strategize then visualize WHAT I need to do. This fulfills the CONTEXT SWITCHING criterion.

With both the Tracking Inbox and Folders of Projects, I now have a rich source of tasks in context to my immediate needs AND my future plans. Now in the morning, I can review the projects and re-prioritize tasks as needed. Then, I can choose to schedule my “most important tasks” with some degree of confidence and bust out an ETP sheet. Or, if I’m feeling “hot” on a particular project, I can just jump in; I might see something in a project list that is, for whatever reason, exactly what I am in the mood to do.

It’s also nice to be able to review the week by looking at the DONE tasks, which Wunderlist sorts in order of completion. You can see what’s done by folder, or see ALL the done tasks. It’s smart enough to group tasks by date, as well, so you can see when you last put in a good chunk of work.

Current Assessment

I’ve been using Wunderlist in this way for about two weeks now, and I think it’s helping me stay on top of everything I want to do. I’m tracking directions and effort, with a bit of context management thrown in.

You’d think that so many to-do list items would be a drag, but since I’m thinking of them not as chores, it’s actually not bad. They’re more like fruit to be plucked when they ripen, and it’s exciting to scan the lists looking for ones that are ready to drop. Could it be that I work better thinking in terms of abundance of choice, as opposed to putting blinders on to focus on just a few things at a time?